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Chemical Structure| 939-26-4 Chemical Structure| 939-26-4

Structure of 939-26-4

Chemical Structure| 939-26-4

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CAS No.: 939-26-4

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Product Citations

Product Citations

Henderson, Ian M. ; Zeng, Fanxun ; Bhuiyan, Nazmul H. ; Luo, Dan ; Martinez, Maria ; Smoake, Jane , et al.

Abstract: Interest in development of potent, selective inhibitors of the phosphatase from the receptor type protein tyrosine phosphatase PTPRD as antiaddiction agents is supported by human genetics, mouse models and studies of our lead compound PTPRD phosphatase inhibitor, 7-butoxy illudalic acid analog 1 (7-BIA). We now report structure-activity relationships for almost 70 7-BIA-related compounds and results that nominate a 7- cyclopentyl methoxy analog as a candidate for further development. While efforts to design 7-BIA analogs with substitutions for other parts failed to yield potent inhibitors of PTPRDs phosphatase, ten 7-position substituted analogs displayed greater potency at PTPRD than 7-BIA. Several were more selective for PTPRD vs the receptor type protein tyrosine phosphatases S, F and J or the nonreceptor type protein tyrosine phosphatase N1 (PTPRS, PTPRF, PTPRJ or PTPN1/PTP1B), phosphatases at which 7-BIA displays activity. In silico studies aided design of novel analogs. A 7-position cyclopentyl methoxy substituted 7-BIA analog termed NHB1109 displayed 600-700 nM potencies in inhibiting PTPRD and PTPRS, improved selectivity vs PTPRS, PTPRF, PTPRJ or PTPN1/PTP1B phosphatases, no substantial potency at other protein tyrosine phosphatases screened, no significant potency at any of the targets of clin.-useful drugs identified in EUROFINS screens and significant oral bioavailability. Oral doses up to 200 mg/kg were well tolerated by mice, though higher doses resulted in reduced weight and apparent ileus without clear organ histopathol. NHB1109 provides a good candidate to advance to in vivo studies in addiction paradigms and toward human use to reduce reward from addictive substances.

Keywords: Receptor type protein tyrosine phosphatase ; Cell adhesion molecule ; Addiction ; Drug reward ; Opiates ; Stimulants

Alternative Products

Product Details of [ 939-26-4 ]

CAS No. :939-26-4
Formula : C11H9Br
M.W : 221.09
SMILES Code : BrCC1=CC=C2C=CC=CC2=C1
MDL No. :MFCD00004123
InChI Key :RUHJZSZTSCSTCC-UHFFFAOYSA-N
Pubchem ID :70320

Safety of [ 939-26-4 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H290-H314-H317
Precautionary Statements:P234-P260-P264-P272-P280-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P333+P313-P362+P364-P390-P405-P406-P501
Class:8
UN#:3261
Packing Group:Ⅱ

Computational Chemistry of [ 939-26-4 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 10
Fraction Csp3 0.09
Num. rotatable bonds 1
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 56.78
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

0.0 ?2

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

2.43
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

3.65
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

3.58
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

4.05
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

4.01
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.54

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-4.06
Solubility 0.0192 mg/ml ; 0.0000869 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-3.34
Solubility 0.101 mg/ml ; 0.000458 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-5.34
Solubility 0.00102 mg/ml ; 0.0000046 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

 Low
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

 Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

 No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

 Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

 Yes
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

 Yes
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

 No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

 No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.06 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

 0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

 None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

 0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

 0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

 1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

 No; 1 violation:MW<2.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

 1.52

Application In Synthesis of [ 939-26-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 939-26-4 ]

[ 939-26-4 ] Synthesis Path-Downstream   1~22

  • 1
  • [ 56-40-6 ]
  • [ 939-26-4 ]
  • [ 6960-34-5 ]
  • 2
  • [ 62327-21-3 ]
  • [ 939-26-4 ]
  • [ 208169-56-6 ]
  • 3
  • [ 939-26-4 ]
  • [ 63024-44-2 ]
  • 5
  • [ 14752-66-0 ]
  • [ 939-26-4 ]
  • 2-(((4-chlorophenyl)sulfonyl)methyl)naphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% A mixture of THF, K2CO3 (0.77 g 0 006 mol) and sodium 4-chloro- benzenesulfinate(0.75 g, 3.7 mmol) was stirred for 15 en blanket and cooled to 0-5 C. <n="19"/>Naphth-2-ylmethylbromide (0.81 g, 3.7 mmol) was added to the reaction mixture. The mixture was stirred at 65 - 67 C for two hours and the solvent was removed by distillation. The resultant solid residue was recrystallized from isopropanol to give the title product, 0.30g, 51% yield, 99% purity by HPLC
In 1,2-dimethoxyethane; at 70℃; for 5h; Example 67: 2-[1-[(4-Chlorophenyl)sulfonyl]-5-(methylsulfonyl)pentyl]naphthalene <strong>[14752-66-0]sodium 4-chlorobenzenesulfinate</strong> (211 mg, 1.06 mmol) and 2-bromomethylnaphthalene (235 mg, 1.06 mmol) were added to dimethoxyethane (5 ml).. The resulting mixture was stirred at 70C for 5 hours.. After cooling to room temperature, the solvent was concentrated under reduced pressure.. The residue was added with ethyl acetate and from the resulting mixture, the insoluble matter was filtered off.. The residue obtained by concentrating the filtrate under reduced pressure was washed with hexane to yield a white powder (90 mg). Then, a toluene (10 ml) solution of the resulting white powder (60 mg), the 4-(methylsulfonyl)-1-butanol (59 mg, 0.388 mmol) obtained in Referential Example 3 and cyanomethylenetri-n-butylphosphorane (91 mg, 0.379 mmol) was heated under reflux for 21 hours under an argon atmosphere.. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure.. The residue was subjected to medium-pressure chromatography on a silica gel column, whereby from the fraction eluted with hexane:ethyl acetate(=2:3), the title compound was obtained as a white solid (62 mg). Melting point: 146.0-147.0C. IR (ATR) ν: 2931, 2861, 1581, 1508, 1473, 1457, 1392, 1359, 1309, 1274, 1191, 1147, 1126, 1081, 1010, 968, 902, 869, 819, 752, 734, 703, 646, 624, 566, 522, 472, 453 cm-1.1H-NMR (400MHz, CDCl3) δ: 1.34-1.51(2H,m), 1.78-1.99(2H,m), 2.25-2.40(1H,m), 2.50-2.62(1H,m), 2.84(3H,s), 2.89-3.03(2H,m), 4.19(1H,dd,J=11.2,3.9Hz), 7.18-7.36(4H,m), 7.39-7.61(4H,m), 7.69-7.90(3H,m). MS (m/z): 451 (M++H). Elemental Analysis for C22H23ClO4S2 Calculated: C 58.59%; H 5.14%; Cl 7.86%; S 14.22%. Found: C 58.46%; H 5.03%; Cl 7.94%; S 14.33%.
  • 6
  • [ 126-33-0 ]
  • [ 5308-63-4 ]
  • [ 939-26-4 ]
  • 1-(2-Naphthylmethyl)-2-acetyl-5-methylpyridinium bromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethyl acetate; 1-(2-Naphthylmethyl)-2-acetyl-5-methylpyridinium bromide Twenty-six grams (0.192 m) of 2-acetyl-5-methylpyridine and 40 g (0.181 m) of 2-bromomethylnaphthalene was added to 78 ml of tetramethylene-sulfone. After heating the mixture for two hours on a steam bath, the mixture was allowed to stand at room temperature for twenty days. The reaction mixture was diluted with 700 ml of ethyl acetate and product oiled out. This first portion of ethyl acetate was decanted and the gum was extracted with 3*100 ml portions of ether. A total of 58 g (85-90%) of gum remained and after storing in the cold for one week some solid formed; however no attempt was made to purify this material further.
  • 7
  • 2-[1-hydroxy-1-(3-methoxy-4-(naphth-2-ylmethoxy)phenyl)propyl]thiazole [ No CAS ]
  • [ 617-05-0 ]
  • [ 939-26-4 ]
  • ethyl 3-methoxy-4-(naphth-2-ylmethoxy)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% y. The 2-[1-hydroxy-1-(3-methoxy-4-(naphth-2-ylmethoxy)phenyl)propyl]thiazole used as a starting material was obtained as follows: 2-Bromomethylnaphthalene was reacted with <strong>[617-05-0]ethyl vanillate</strong> using the conditions described in Example 1 to give ethyl 3-methoxy-4-(naphth-2-ylmethoxy)benzoate in 54% yield, m.p. 86-87 C. Following the procedures described in the portion of Example 6 which is concerned with the preparation of starting materials the product so obtained was reacted with thiazol-2-yl-lithium and the resultant product was reacted with ethylmagnesium iodide to give the required starting material as an oil in 20% yield, m.p. 124-126 C. (recrystallized from a mixture of hexane and ethyl acetate).
  • 8
  • [ 6374-91-0 ]
  • [ 939-26-4 ]
  • [ 1020265-01-3 ]
  • 9
  • [ 68631-52-7 ]
  • [ 939-26-4 ]
  • [ 1245503-98-3 ]
  • 10
  • [ 133730-34-4 ]
  • [ 939-26-4 ]
  • [ 1271736-90-3 ]
YieldReaction ConditionsOperation in experiment
70% With potassium phosphate; palladium diacetate; triphenylphosphine; In toluene; at 100℃; for 16h;Inert atmosphere; General procedure: 2,4-Dimethoxyphenyl boronic acid (0.205 g, 1.5 equiv.) in dry toluene (4 mL) was reacted at room temperature for 10 min with benzyl halide (1.0 equiv.) in the presence of K3PO4 (2.0 equiv.), PPh3 (0.02 equiv.) and Pd(OAc)2 (0.01 equiv.) under argon atmosphere. Bromine derivative (1.0 equiv.) was added and the reaction was heated at 100 C for 16 h. A solution of NaOH (1 M) was added and the crude product was extracted with diethyl ether. Final compounds were purified by column chromatography over silica gel.
  • 11
  • [ 112881-51-3 ]
  • [ 939-26-4 ]
  • [ 1442636-91-0 ]
  • 12
  • [ 42726-73-8 ]
  • [ 939-26-4 ]
  • 1-tert-butyl 3-methyl 2-benzoyloxy-2-naphthalen-2-ylmethylmalonate [ No CAS ]
  • 13
  • [ 42726-73-8 ]
  • [ 939-26-4 ]
  • 1-tert-butyl 3-methyl 2-naphthalen-2-ylmethylmalonate [ No CAS ]
  • 14
  • [ 50790-93-7 ]
  • [ 939-26-4 ]
  • C18H20N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
2-Butylimidazole (0.500 g, 4.0 mmol) wasdissolved in organic dry tetrahydrofuran (10 mL) and added to a stirred slurryof sodium hydride (0.14 g, 5.8 mmol) in organic dry tetrahydrofuran (10 mL)cooled to 0C in an ice bath. After 30 minutes, tetrabutylammonium bromide(0.070 g, 0.2 mmol) was added to the reaction mixture. 2-(Bromomethyl)naphthalene(1.00 g, 4.5 mmol) dissolved in organic dry tetrahydrofuran (15 mL) was slowlyadded to the reaction mixture dropwise over 15 minutes. Reaction was warmed toroom temperature and stirred for 4 hours. The mixture was filtered throughcelite and the volatiles were removed from the filtrate to form a light yellowoil. The oil was suspended in water (30 mL) and extracted with dichloromethane(3 x 30 mL). The organic layers were combined, washed with water (3 x 30 mL),and dried with magnesium sulfate. The volatiles were removed to form a lightyellow solid. The mono-alkylated intermediate was dissolved in acetone leavinga white precipitate that was removed by filtration. The volatiles were removedfrom the filtrate to form a light yellow residue. This residue was resuspendedin acetonitrile (5 mL), combined with 2-(chloromethyl)quinoline (0.735 g, 4.2mmol), and heated to 80C overnight. A white solid precipitated from thereaction mixture which was washed with room temperatureacetonitrile and diethyl ether. The white solid was dissolved indichloromethane followed by removal of all volatiles by rotary evaporation and byvacuum with the compound under reduced pressure for 6 days to yield 6 (0.256 g, 17% yield). Mp: 170-173C. HRMS(ESI+) calcd for C28H28N3+[M-Cl] of m/z = 406.2278, found m/z = 406.2304. 1H NMR (500 MHz,DMSO- d6) delta = 8.48 (1H, d,Ar, J = 8.6 Hz), 8.01 (4H, m, Ar), 7.97 (1H, m, Ar), 7.92 (2H, m, Ar, 7.76 (2H,m, Ar), 7.67 (1H, d, Ar, J = 8.6 Hz), 7.61 (1H, m, Ar), 7.57 (2H, m, Ar), 7.51(1H, d, Ar, J = 8.3 Hz), 5.93 (2H, s, CH2), 5.78 (2H, s, CH2),3.12 (2H, m, CH2), 1.15 (4H, m, CH2, CH2),0.51 (3H, m, CH3) . 13C NMR (125 MHz, DMSO- d6) delta = 154.2 (Ar), 148.1(Ar), 146.2 (Ar), 137.4 (Ar), 132.6 (Ar), 132.5 (Ar), 132.4 (Ar), 130.1(Ar), 128.7 (Ar), 128.3 (Ar), 127.9 (Ar), 127.7 (Ar), 127.6 (Ar), 127.1 (Ar),126.9 (Ar), 126.7 (Ar), 126.6 (Ar), 126.6 (Ar), 125.1 (Ar), 123.2 (Ar), 122.2(Ar), 119.9 (Ar), 52.4 (CH2), 51.0 (CH2), 28.3 (CH2),22.8 (CH2), 21.5 (CH2), 13.1 (CH3).
General procedure: Potassium hydroxide was added to a stirred solution of the 2-alkylimidazole in hot acetonitrile (~ 80 C), and the reaction was stirred for one hour. 2-(Bromomethyl)naphthalene was added to the mixture, which was refluxed overnight. An insoluble material formed and was removed by filtration. 2-(Bromomethyl)naphthalene was added to the filtrate and the mixture was refluxed overnight. The product precipitated from hot acetonitrile, or precipitation was induced by addition of diethyl ether. The solid was collected by filtration, washed with diethyl ether, air dried, and recrystallized from the appropriate solvent to yield the product.
  • 15
  • [ 50790-93-7 ]
  • [ 939-26-4 ]
  • 2-butyl-3-(naphthalen-2-ylmethyl)-1-(quinolin-2-ylmethyl)imidazolium chloride [ No CAS ]
  • 16
  • [ 50790-93-7 ]
  • [ 939-26-4 ]
  • 2-butyl-1,3-bis(naphthalen-2-ylmethyl)imidazolium bromide [ No CAS ]
  • 17
  • [ 38116-61-9 ]
  • [ 939-26-4 ]
  • 6-methyl-2-(naphthalen-2-ylmethoxy)nicotinic acid [ No CAS ]
  • 18
  • [ 39998-25-9 ]
  • [ 939-26-4 ]
  • methyl 3-(naphthalen-2-yl)-2-(pyridin-3-yl)propanoate [ No CAS ]
  • 19
  • [ 39998-25-9 ]
  • [ 939-26-4 ]
  • methyl 2-methyl-3-(naphthalen-2-yl)-2-(pyridin-3-yl)propanoate [ No CAS ]
  • 20
  • [ 492-30-8 ]
  • [ 939-26-4 ]
  • C39H34O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% The raw material 5 (5.0 g, 30 . 84 mmol) [according to Tetrahedron: Asymmetry 2007, 18, 500 - 512 method preparation] dissolved in anhydrous DMF (200 ml) in, nitrogen protection, cooling to -10 C, slowly added 60% NaH (1.6 g, 40 . 09 mmol), in -10 C stirring reaction for 1 hour later, slowly adding 2 - bromo naphthalene (10.2 g, 46 . 26 mmol), continuing to stir 30 minutes later, according to the above-mentioned operation by adding 60% NaH (1.6 g, 40 . 09 mmol) and 2 - bromo naphthalene (10.2 g, 46 . 26 mmol), repeated two, keeping the temperature at -10 C stirring reaction 48 hours later, the reaction solution is poured into a 500 ml ice water quenching of the reaction, ethyl acetate (100 mLx 4) extraction, the combined organic phase, 200 ml saturated salt water washing of the organic layer, anhydrous sodium sulfate drying, concentrating, separating by silica gel column (10:1, V/V, petroleum ether: EtOAc) to obtain colourless oily product 5 - 1 the a (12.6 g, 21 . 59 mmol), yield: 70%.
70% Starting material 6-1c (5.0 g, 30.84 mmol) was dissolved in anhydrous DMF (200 mL). Protected with nitrogen and cooled to -10 C, Slowly add 60% NaH (1.6 g, 40.09 mmol), After stirring at -10 C for 1 hour, 2-Bromomethylnaphthalene (10.2 g, 46.26 mmol) was slowly added. After stirring for another 30 minutes, Add 60% NaH (1.6g, 40.09mmol) as above. And 2-bromomethylnaphthalene (10.2 g, 46.26 mmol), Repeat twice, After maintaining the temperature at -10 C for 48 hours, The reaction solution was poured into 500 mL of ice water to quench the reaction. Extracted with ethyl acetate (100 mL x 4), Combine the organic phase, The organic layer was washed with 200 mL of saturated brine. Dry over anhydrous sodium sulfate, concentrate, Separation on silica gel column (10:1, V/V, petroleum ether: EtOAc) The colorless oily product 2-1c (12.6 g, 21.59 mmol), Yield: 70%.
  • 21
  • [ 492-30-8 ]
  • [ 939-26-4 ]
  • C36H28O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% Starting material 3 (5.0 g, 30.84 mmol) [prepared according to Tetrahedron: Asymmetry 2007, 18, 500-512] was dissolved in anhydrous DMF (200 mL).Protected with nitrogen and cooled to -10 ° C,Slowly add 60percent NaH (1.6 g, 40.09 mmol),After stirring at -10 ° C for 1 hour,2-Bromomethylnaphthalene (10.2 g, 46.26 mmol) was slowly added.After stirring for another 30 minutes,Add 60percent NaH (1.6g, 40.09mmol) as above.And 2-bromomethylnaphthalene (10.2 g, 46.26 mmol),Repeat twice, keep the temperature at -10 ° C and stir the reaction for 48 hours.The reaction mixture was poured into 500 mL of ice water to quench the reaction, and extracted with ethyl acetate (100 mL×4).The organic layer was washed with 200 mL of brine, dried over anhydrous sodium sulfateOn a silica column (10: 1, V / V, petroleum ether: EtOAc) to give a white oily product 3-1a (12.6g, 21.59mmol),Yield: 70percent.
 

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