[ CAS No. 40473-07-2 ] {[proInfo.proName]}

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2D 3D

Structure of 40473-07-2 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 40473-07-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 40473-07-2 ]

SDS Specification

Alternatived Products of [ 40473-07-2 ]

Product Details of [ 40473-07-2 ]

CAS No. :	40473-07-2	MDL No. :	MFCD00088345
Formula :	C₆H₆BrNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KMODISUYWZPVGV-UHFFFAOYSA-N
M.W :	188.02	Pubchem ID :	256810
Synonyms :

Calculated chemistry of [ 40473-07-2 ] Expand+

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.17
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	38.43
TPSA :	22.12 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.3 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.22
Log Po/w (XLOGP3) :	3.02
Log Po/w (WLOGP) :	1.85
Log Po/w (MLOGP) :	1.33
Log Po/w (SILICOS-IT) :	2.04
Consensus Log Po/w :	2.09

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.34
Solubility :	0.0868 mg/ml ; 0.000462 mol/l
Class :	Soluble
Log S (Ali) :	-3.15
Solubility :	0.133 mg/ml ; 0.000709 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.01
Solubility :	0.185 mg/ml ; 0.000986 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.88

Safety of [ 40473-07-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 40473-07-2 ]

* 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.

Upstream synthesis route of [ 40473-07-2 ]
Downstream synthetic route of [ 40473-07-2 ]

[ 40473-07-2 ] Synthesis Path-Upstream 1~3

1
[ 40473-07-2 ]
[ 544-92-3 ]
[ 83621-01-6 ]

Yield	Reaction Conditions	Operation in experiment
44%	at 20 - 165℃; for 15 h;	[Referential Example 21]; 6-Methoxypyridine-2-carbonitrile; Copper(I) cyanide (2.68 g) was added to 2-bromo-6-methoxypyridine (5.62 g) in N,N-dimethylformamide (112 mL) at room temperature, followed by stirring at 165°C for 15 hours. The resultant mixture was cooled in air. Water and ethyl acetate was added to the mixture. The insoluble matter that was formed in the mixture was filtered by Celite. The filtrate was partitioned between water and ethyl acetate. The organic layer was dried over sodium sulfate anhydrate, followed by filtration. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane - ethyl acetate), to thereby give the title compound as a solid substance (1.78 g, 44percent) .1H-NMR(400MHz,CDCl3)δ: 3.96(3H,s), 6.95-6.98(1H,m), 7.29-7.31(1H,m), 7.64-7.67(1H,m). MS (EI)m/z: 134 (M+) .

Reference： [1] Synlett, 2001, # 6, p. 765 - 768
[2] Journal of the Chemical Society. Perkin Transactions 1, 2002, vol. 2, # 1, p. 58 - 68
[3] Patent: EP1591443, 2005, A1, . Location in patent: Page/Page column 33

2
[ 557-21-1 ]
[ 40473-07-2 ]
[ 83621-01-6 ]

Reference： [1] Organic Letters, 2015, vol. 17, # 2, p. 202 - 205
[2] Tetrahedron Letters, 2004, vol. 45, # 48, p. 8895 - 8897

3
[ 40473-07-2 ]
[ 83621-01-6 ]

Yield	Reaction Conditions	Operation in experiment
39%	at 20 - 100℃; for 16 h;	Synthesis of 6-methoxypicolinonitrile:To a stirred solution of 2-bromo-6-methoxypyridine (5.0 g, 26.59 mmol) in DMF (50 mL) was added Cu(I)cyanide (7.14 g, 79.77 mmol) at room temperature. The resulting reaction mixture was heated at 100 °C and stirred for 16 h. The reaction mixture was diluted with water, filtered through a pad of celite and the filtrate was extracted with EtOAc. Combined organic layer was dried over sodium sulphate, filtered and concentrated in vacuo to obtain the crude product. The crude material was purified by silica gel column chromatography to afford 6-methoxypicolinonitrile (1.4 g, 39percent) as white solid. 1H-NMR (DMSO d₆, 400 MHz): δ 7.94 (t, 1H), 7.64 (d, 1H), 7.18 (d, 1H), 3.92 (s, 3H); LC-MS: 99.14percent; 135.8 (M⁺+l); (column; X-bridge C-18, (50x3.0 mm, 3.5μ); RT 3.31 min. 0.1percent Aq TFA: ACN; 0.8 ml/min); TLC: 10percent EtOAc/Hexane (Rf:
39%	at 100℃; for 16 h;	Synthesis of 6-methoxypicolinonitrile [0524] To a stirred solution of 2-bromo-6-methoxypyridine (5.0 g, 26.59 mmol) in DMF (50 mL) was added Cu(I)cyanide (7.14 g, 79.77 mmol) at room temperature. The resulting reaction mixture was heated at 100 °C and stirred for 16 h. The reaction mixture was diluted with water, filtered through a pad of celite and the filtrate was extracted with EtOAc. Combined organic layer was dried over sodium sulphate, filtered and concentrated in vacuo to obtain the crude product. The crude material was purified by silica gel column chromatography to afford 6-methoxypicolinonitrile (1.4 g, 39percent) as white solid. 1H-NMR (DMSO d₆, 400 MHz): δ 7.94 (t, IH), 7.64 (d, IH), 7.18 (d, IH), 3.92 (s, 3H); LC-MS: 99.14percent; 135.8 (M⁺+l); (column; X-bridge C-18, (50x3.0 mm, 3.5μ); RT 3.31 min. 0.1percent Aq TFA: ACN; 0.8 ml/min); TLC: 10percent EtOAc/Hexane (Rf: 0.3).

Reference： [1] Patent: WO2012/40230, 2012, A1, . Location in patent: Page/Page column 86
[2] Patent: WO2013/142269, 2013, A1, . Location in patent: Paragraph 0523; 0524

[ 40473-07-2 ] Synthesis Path-Downstream 1~4

1
[ 40473-07-2 ]
[ 68-12-2 ]
[ 54221-96-4 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of the compound of Preparation 113 (5.6 g, 29.8 mmol) in anhydrous tetrahydrofuran (100 ml), at -78° C. and under nitrogen, was added n-butyllithium (1.6M in hexane, 19.5 ml), via syringe. The mixture was stirred at -78° C. for 30 min, before addition of N,N-dimethylformamide (2.5 ml, 32.8 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 18 h, before being acidified with sulphuric acid (2M) and then neutralised by addition of sodium hydrogen carbonate. The mixture was concentrated in vacuo and the residue was extracted with ethyl acetate (4*150 ml). The combined extracts were dried (MgSO4) and concentrated in vacuo to give the title compound (3.0 g). 1H-NMR (CDCl3): 4.01-4.05 (3H), 6.95-7.00 (1H), 7.54-7.58 (1H), 7.70-7.76 (1H), 9.95-9.98 (1H)

Reference： [1]European Journal of Organic Chemistry,2002,p. 2126 - 2135
[2]Synthesis,2012,vol. 44,p. 735 - 746
[3]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 3130 - 3141
[4]Tetrahedron,2005,vol. 61,p. 6207 - 6217
[5]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 6763 - 6770
[6]Journal of Organic Chemistry,1990,vol. 55,p. 69 - 73
[7]Patent: US2008/103130,2008,A1 .Location in patent: Page/Page column 50
[8]Patent: US2007/173508,2007,A1 .Location in patent: Page/Page column 90

2
[ 40473-07-2 ]
[ 909720-21-4 ]
3,6-dibromo-2-methoxypyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-Bromosuccinimide; In acetonitrile; at 80 - 90℃; for 24.0h;	Example 260 2,3-dibromo-6-methoxypyridine NBS (302 g) was added to the compound of Example 259 (295 g) in acetonitrile (575 mL) and the mixture was stirred at 80 to 90 C. for 1 day in a nitrogen atmosphere. After cooling, the crystallized imide was removed by filtration and the filtrate was concentrated. Purification of the resulting residue by silica gel column chromatography (ether:petroleum ether=1:1) gave a 6:1 mixture of the title compound and 2,5-dibromo form. This product was crystallized from cold petroleum ether to afford the title compound as a colorless powder (223 g). 1H NMR (200 MHz, CDCl3) delta 6.68 (1H, d, J=8.7 Hz), 6.60 (1H, d, J=8.7 Hz), 3.91 (3H, s). 13C NMR (50 MHz, CDCl3) delta 162.01, 143.29, 139.68, 113.69, 111.10, 54.40 LRMS (EI+): 264[M+]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 3307 - 3312
[2]Patent: US2008/207902,2008,A1 .Location in patent: Page/Page column 64

3
[ 40473-07-2 ]
[ 955368-90-8 ]
2-allyl-1-(6-methoxypyridin-2-yl)-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3_,4-d]pyrimidin-3-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With copper(l) iodide; potassium carbonate; N,N-dimethylethylenediamine; In 1,4-dioxane; at 95℃; for 12h;Inert atmosphere;	I1 (1.0 g, 4.5 mmol) was added into 1,4- dioxane (10 mL), and 2-bromo-6-methoxylpyridine (1.02 g, 5.4 mmol, 664 muL), potassium carbonate (622 mg, 4.5 mmol), cuprous iodide (857 mg, 4.5 mmol) and N,N'-dimethylethylenediamine (397 mg, 4.5 mmol, 490 muL) were added while stirring, heated to 95C under nitrogen atmosphere, then reacted for 12 h. 100 mL ammonia was added into the reacted mixture, then extracted by 100 mL EA, the organic phase was washed by 100 mL brine, dried over anhydrous sodium sulfate, filtered and concentrated, the crude product was crystalized by EtOAc, then purified by silica gel chromatography (PE/EA = 10/1 to 2/1), to give the compound 47-1. 1H NMR (400MHz, CDCl3) delta = 8.92 (s, 1H), 7.89 (t, J=8.0 Hz, 1H), 7.43 (d, J=7.2 Hz, 1H), 6.82 (d, J=8.0 Hz, 1H), 5.83 - 5.69 (m, 1H), 5.07 (d, J=10.4 Hz, 1H), 4.96 (br d, J=17.2 Hz, 1H), 4.84 (d, J=6.0 Hz, 2H), 3.93 (s, 3H), 2.56 (s, 3H)

Reference： [1]ACS Chemical Biology,2016,vol. 11,p. 921 - 930
[2]Patent: EP3572413,2019,A1 .Location in patent: Paragraph 0320-0322

4
[ 40473-07-2 ]
[ 955368-90-8 ]
C₃₀H₃₆N₈O₂ [ No CAS ]

Reference： [1]Patent: EP3572413,2019,A1

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Technical Information

? Alkyl Halide Occurrence ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Nomenclature of Ethers ? Preparation of Amines ? Preparation of Ethers ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Dihalides ? Reactions of Ethers ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling

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[ 40473-07-2 ]

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H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 40473-07-2 ] {[proInfo.proName]}

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Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

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Application In Synthesis of [ 40473-07-2 ]

[ 40473-07-2 ] Synthesis Path-Upstream 1~3

[ 40473-07-2 ] Synthesis Path-Downstream 1~4

Technical Information

Related Functional Groups of [ 40473-07-2 ]

Bromides

Ethers

Related Parent Nucleus of [ 40473-07-2 ]

Pyridines

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Prevention

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Disposal

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Environmental hazards

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[ 40473-07-2 ]

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[ 40473-07-2 ]