[ CAS No. 42933-43-7 ] {[proInfo.proName]}

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Quality Control of [ 42933-43-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 42933-43-7 ]

SDS Specification

Alternatived Products of [ 42933-43-7 ]

Product Details of [ 42933-43-7 ]

CAS No. :	42933-43-7	MDL No. :	MFCD03617969
Formula :	C₈H₉NO	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	YJMADHMYUJFMQE-UHFFFAOYSA-N
M.W :	135.16	Pubchem ID :	3841102
Synonyms :

Calculated chemistry of [ 42933-43-7 ] Expand+

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	40.19
TPSA :	35.25 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.09 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.54
Log Po/w (XLOGP3) :	1.46
Log Po/w (WLOGP) :	1.21
Log Po/w (MLOGP) :	1.09
Log Po/w (SILICOS-IT) :	1.82
Consensus Log Po/w :	1.42

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.04
Solubility :	1.23 mg/ml ; 0.00908 mol/l
Class :	Soluble
Log S (Ali) :	-1.81
Solubility :	2.11 mg/ml ; 0.0156 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.3
Solubility :	0.682 mg/ml ; 0.00505 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.54

Safety of [ 42933-43-7 ]

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

Application In Synthesis of [ 42933-43-7 ]

* 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 [ 42933-43-7 ]
Downstream synthetic route of [ 42933-43-7 ]

[ 42933-43-7 ] Synthesis Path-Upstream 1~7

1
[ 17403-47-3 ]
[ 42933-43-7 ]

Yield	Reaction Conditions	Operation in experiment
97.2%	With hydrogen In methanol at 20℃;	Step 2: Preparation of 5-amino-2,3-dihydrobenzofuran [Show Image] The product (1 g, 6.1 mmol) obtained in Step 1, Raney Ni (0.1 g) and MeOH(10 mL) were used for hydrogenation at room temperature and hydrogen pressure of 50 PSI, until the reaction was finished. The catalyst was removed by filtration, the fitrate was concentrated under vacuum to obtain a product (800 mg, 97.2percent).
90%	With palladium 10% on activated carbon; hydrogen In ethanol; water for 13 h;	A mixture of 21 (6.3 g, 38.1 mmol) and 10percent palladium on carbon (1.0 g) in EtOH (50 mL) and THF (50 mL) was stirred under an atmosphere of H₂ (1 atm) at room temperature for 13 h. The catalyst was removed by filtration, and then the filtrate was concentrated. The residue was purified by flash chromatography on SiO₂ with a gradient eluent of 0-10percent MeOH/EtOAc to provide 22 (4.63 g, 90percent) as a pale brown powder; ¹H NMR (CDCl₃) δ: 3.12 (2H, t, J = 8.6 Hz), 3.37 (2H, s), 4.49 (2H, t, J = 8.6 Hz), 6.43-6.47 (1H, m) 6.57-6.61 (2H, m); Anal. Calcd for C₈H₉NO: C, 71.09; H, 6.71; N, 10.36. Found: C, 70.92; H, 6.60; N, 10.09.

Reference： [1] Journal of Medicinal Chemistry, 2010, vol. 53, # 18, p. 6681 - 6698
[2] Patent: EP2532665, 2012, A1, . Location in patent: Page/Page column 21
[3] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 21, p. 6430 - 6446
[4] Journal of Medicinal Chemistry, 2014, vol. 57, # 13, p. 5579 - 5601
[5] Journal of Medicinal Chemistry, 2009, vol. 52, # 14, p. 4161 - 4172
[6] Patent: WO2003/82787, 2003, A1, . Location in patent: Page/Page column 139
[7] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 13, p. 3821 - 3830

2
[ 18761-31-4 ]
[ 42933-43-7 ]

Yield	Reaction Conditions	Operation in experiment
92%	With hydrogen In ethanol for 5 h;	Preparation 101 ; 2, 3-Dihvdro-benzofuran-5-vlamine; The product of preparation 100 (5. 0g, 31mmol) and 10percent Pd/C (1.25g) was added to ethanol (100mL) and the mixture was stirred under 55psi of hydrogen gas for 5 hours. The reaction mixture was then filtered through Celite and the filtrate was concentrated in vacuo to afford the title product as a pale brown powder in 92percent yield. MS ES+ m/z 135 [M+]. m. p. 73-77°C

Reference： [1] Patent: WO2005/82866, 2005, A2, . Location in patent: Page/Page column 97
[2] Patent: US2003/195201, 2003, A1,

3
[ 496-16-2 ]
[ 42933-43-7 ]

Reference： [1] ACS Catalysis, 2016, vol. 6, # 12, p. 8162 - 8165
[2] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 21, p. 6430 - 6446
[3] Patent: EP2532665, 2012, A1,
[4] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 13, p. 3821 - 3830
[5] Journal of Medicinal Chemistry, 2014, vol. 57, # 13, p. 5579 - 5601

4
[ 58546-89-7 ]
[ 42933-43-7 ]

Reference： [1] Tetrahedron Letters, 1996, vol. 37, # 27, p. 4631 - 4634

5
[ 496-16-2 ]
[ 42933-43-7 ]
[ 13414-56-7 ]

Reference： [1] Chemistry - A European Journal, 2017, vol. 23, # 3, p. 563 - 567

6
[ 17403-47-3 ]
[ 42933-43-7 ]

Reference： [1] Patent: US3963717, 1976, A,

7
[ 7169-34-8 ]
[ 42933-43-7 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 13, p. 3821 - 3830

[ 42933-43-7 ] Synthesis Path-Downstream 1~23

1
[ 42933-43-7 ]
3-{4-[4-(2,3-dihydro-benzofuran-5-yl)-piperazin-1-yl]-butyl}-5-methoxy-1<i>H</i>-indole [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4677 - 4683

2
[ 42933-43-7 ]
1-[4-(2,3-dihydrobenzofuran-5-yl)piperazin-1-yl]-4-(5-methoxy-1H-indol-3-yl)butan-1-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4677 - 4683

3
[ 18761-31-4 ]
[ 42933-43-7 ]

Yield	Reaction Conditions	Operation in experiment
92%	With hydrogen;palladium 10% on activated carbon; In ethanol; under 2844.39 Torr; for 5h;	Preparation 101 ; 2, 3-Dihvdro-benzofuran-5-vlamine; The product of preparation 100 (5. 0g, 31mmol) and 10percent Pd/C (1.25g) was added to ethanol (100mL) and the mixture was stirred under 55psi of hydrogen gas for 5 hours. The reaction mixture was then filtered through Celite and the filtrate was concentrated in vacuo to afford the title product as a pale brown powder in 92percent yield. MS ES+ m/z 135 [M+]. m. p. 73-77°C
	Pd on carbon; In ethyl acetate;	(a) 2,3-Dihydrobenzo[b]furan-5-ylamine. To a 150 mL round-bottomed flask was added 5-nitrobenzofuran, Example 38(d), (250 mg, 1.5 mmol), EtOAc (16 mL) and 10percent Pd on carbon (33 mg, Aldrich). The suspension was stirred at 25° C. under 1 atm H2 for 24 h, then purged with N2, filtered through Celite and concentrated in vacuo to provide the aniline as a red-brown solid. MS (ESI, pos. ion) m/z: 136 (M+1).

Reference： [1]Patent: WO2005/82866,2005,A2 .Location in patent: Page/Page column 97
[2]Patent: US2003/195201,2003,A1

4
[ 42933-43-7 ]
[ 81926-25-2 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic anhydride; In acetic acid;	(a) 9.5 g of <strong>[42933-43-7]2,3-dihydrobenzo[b]furan-5-amine</strong> in 40 ml of acetic acid and 10 ml of acetic anhydride is heated to 60° C. for 11/2 hours and concentrated. The residue is recrystallized from aqueous ethanol. Yield: 11.5 g of N-(2,3-dihydrobenzo[b]furan-5-yl)acetamide, mp 96° C.

Reference： [1]Patent: US4411910,1983,A

5
[ 75-30-9 ]
[ 42933-43-7 ]
N-isopropyl-2,3-dihydro-5-benzofuranamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In methanol;	Step a: preparation of N-isopropyl-<strong>[42933-43-7]2,3-dihydro-5-benzofuranamine</strong> To a solution of 40 g. of <strong>[42933-43-7]2,3-dihydro-5-benzofuranamine</strong> in 200 ml. of methanol is added 23 ml. of isopropyl iodide and 35 ml. of triethylamine. The solution is refluxed for 55 hours and then concentrated in vacuo. The resultant oil is extracted several times with diethyl ether, the extract combined, filtered through Celite, and the ether removed in vacuo to obtain an oil of N-isopropyl-<strong>[42933-43-7]2,3-dihydro-5-benzofuranamine</strong>.

Reference： [1]Patent: US3963717,1976,A

6
tris(dibenzylideneacetone)dipalladium ⁽⁰⁾ [ No CAS ]
[ 3972-65-4 ]
[ 42933-43-7 ]
[ 941695-82-5 ]

Yield	Reaction Conditions	Operation in experiment
	With nitrogen; sodium t-butanolate; In toluene;	Example 5 Preparation of N-(4-tert-butylphenyl)-<strong>[42933-43-7]2,3-dihydro-1-benzofuran-5-amine</strong> To a flask equipped with a magnetic stirrer, reflux condensor, and nitrogen inlet was added <strong>[42933-43-7]2,3-dihydro-1-benzofuran-5-amine</strong> (11.6 grams, 85.8 mmoles, prepared as in Example 23 of U.S. Pat. No. 20040029932), 4-tert-butyl bromobenzene (18.1 grams, 85 mmoles), tris(dibenzylideneacetone)dipalladium (0) (1.6 grams, 1.7 mmoles), rac-2,2'-bis(diphenylphosphino)-1,1'-binapthyl (2.1 grams, 3.4 mmoles), sodium tert-butoxide (16.4 grams, 0.17 moles) and anhydrous toluene (100 mL). The contents of the flask were refluxed for three days; cooled to room temperature; and filtered through a pad of silica gel. The silica gel pad was then eluted with dichloromethane (150 mL). The combined organic layers were concentrated in vacuo to yield a dark solid. The solid was chromatographed on silica gel, eluding with hexane/ethyl acetate (20:1) to afford 10 grams of the desired product as a white solid. 1H NMR (CDCl3) delta 7.25 (d, 2H), 6.95 (s, 1H), 6.85 (d, 3H), 6.7 (d, 1H), 5.4 (bs, 1H), 4.5 (t, 2H), 3.15 (t, 2H), 1.3 (s, 9H).

Reference： [1]Patent: US2007/142246,2007,A1

7
[ 3972-65-4 ]
[ 42933-43-7 ]
[ 941695-82-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; for 72h;Heating / reflux;	Example 5; Preparation of N-(4-tert-butylphenyl)-<strong>[42933-43-7]2,3-dihydro-1-benzofuran-5-amine</strong>; [Show Image] To a flask equipped with a magnetic stirrer, reflux condensor, and nitrogen inlet was added <strong>[42933-43-7]2,3-dihydro-1-benzofuran-5-amine</strong> (11.6 grams, 85.8 mmoles, prepared as in Example 23 of U.S. Pat. No. 20040029932), 4-tert-butyl bromobenzene (18.1 grams, 85 mmoles), tris(dibenzylideneacetone)dipalladium (0) (1.6 grams, 1.7 mmoles), rac-2,2'-bis(diphenylphosphino)-1,1'-binapthyl (2.1 grams, 3.4 mmoles), sodium tert-butoxide (16.4 grams, 0.17 moles) and anhydrous toluene (100 mL). The contents of the flask were refluxed for three days; cooled to room temperature; and filtered through a pad of silica gel. The silica gel pad was then eluted with dichloromethane (150 mL). The combined organic layers were concentrated in vacuo to yield a dark solid. The solid was chromatographed on silica gel, eluting with hexane/ethyl acetate (20:1) to afford 10 grams of the desired product as a white solid. 1H NMR (CDCl3) delta 7.25 (d, 2H), 6.95 (s, 1H), 6.85 (d, 3H), 6.7 (d, 1H), 5.4 (bs, 1H), 4.5 (t, 2H), 3.15 (t, 2H), 1.3 (s, 9H).
	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; for 72h;Heating / reflux;	To a flask equipped with a magnetic stirrer, reflux condensor, and nitrogen inlet was added <strong>[42933-43-7]2,3-dihydro-1-benzofuran-5-amine</strong> (11.6 grams, 85.8 mmoles, prepared as in Example 23 of U.S. Pat. No. 20040029932), 4-tert-butyl bromobenzene (18.1 grams, 85 mmoles), tris(dibenzylideneacetone)dipalladium (0) (1.6 grams, 1.7 mmoles), rac-2,2'-bis(diphenylphosphino)-1,1'-binapthyl (2.1 grams, 3.4 mmoles), sodium tert-butoxide (16.4 grams, 0.17 moles) and anhydrous toluene (100 mL). The contents of the flask were refluxed for three days; cooled to room temperature; and filtered through a pad of silica gel. The silica gel pad was then eluted with dichloromethane (150 mL). The combined organic layers were concentrated in vacuo to yield a dark solid. The solid was chromatographed on silica gel, eluting with hexane/ethyl acetate (20:1) to afford 10 grams of the desired product as a white solid. 1H NMR (CDCl3) delta 7.25 (d, 2H), 6.95 (s, 1H), 6.85 (d, 3H), 6.7 (d, 1H), 5.4 (bs, 1H), 4.5 (t, 2H), 3.15 (t, 2H), 1.3 (s, 9H).

Reference： [1]Patent: EP1801104,2007,A2 .Location in patent: Page/Page column 12
[2]Patent: US7501386,2009,B2 .Location in patent: Page/Page column 21-22

8
[ 66826-78-6 ]
tris(dibenzylideneacetone)dipalladium ⁽⁰⁾ [ No CAS ]
[ 42933-43-7 ]
N-(2,3-dihydro-1-benzofuran-5-yl)-2,3-dihydro-1-benzofuran-5-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With nitrogen; sodium t-butanolate; In toluene;	Example 3 Preparation of N-(2,3-dihydro-1-benzofuran-5-yl)-2,3-dihydro-1-benzofuran-5 -amine To a flask equipped with a magnetic stirrer, reflux condenser, and nitrogen inlet was added <strong>[42933-43-7]2,3-dihydro-1-benzofuran-5-amine</strong> (4.53 grams, 33.3 mmoles, prepared as in Example 23 of U.S. Pat. No. 20040029932), 5-bromo-2,3-dihydrobenzofuran (6.63 grams, 32.9 mmoles), tris(dibenzylideneacetone)dipalladium (0) (0.61 grams, 0.67 mmoles), rac-2,2'-bis(diphenylphosphino)-1,1'-binapthyl (0.83 grams, 1.33 mmoles), sodium tert-butoxide (6.44 grams, 66.6 mmoles) and anhydrous toluene (60 mL). The contents of the flask were refluxed for three days; cooled to room temperature; and filtered through a pad of silica gel. The silica gel pad was then eluted with dichloromethane (200 mL). The combined organic layers were concentrated in vacuo to yield a dark yellow oil. The solid was chromatographed on silica gel, eluding with a hexane/ethyl acetate gradient. The resulting solid was recrystallized from ethanol to afford 1.8 grams of the desired product as a white solid. 1H NMR (CDCl3/D2O) delta 6.55-6.95 (m, 6H), 4.5 (t, 4H), 3.15 (t, 4H).

Reference： [1]Patent: US2007/142245,2007,A1

9
[ 66826-78-6 ]
[ 42933-43-7 ]
N-(2,3-dihydro-1-benzofuran-5-yl)-2,3-dihydro-1-benzofuran-5-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; for 72h;Heating / reflux;	Example 3 Preparation of N-(2,3-dihydro-1-benzofuran-5-yl)-<strong>[42933-43-7]2,3-dihydro-1-benzofuran-5-amine</strong> To a flask equipped with a magnetic stirrer, reflux condensor, and nitrogen inlet was added <strong>[42933-43-7]2,3-dihydro-1-benzofuran-5-amine</strong> (4.53 grams, 33.3 mmoles, prepared as in Example 23 of), 5-bromo-2,3-dihydrobenzofuran (6.63 grams, 32.9 mmoles), tris(dibenzylideneacetone)dipalladium (0) (0.61 grams, 0.67 mmoles), rac-2,2'-bis(diphenylphosphino)-1,1'-binapthyl (0.83 grams, 1.33 mmoles), sodium tert-butoxide (6.44 grams, 66.6 mmoles) and anhydrous toluene (60 mL). The contents of the flask were refluxed for three days; cooled to room temperature; and filtered through a pad of silica gel. The silica gel pad was then eluted with dichloromethane (200 mL). The combined organic layers were concentrated in vacuo to yield a dark yellow oil. The solid was chromatographed on silica gel, eluding with a hexane/ethyl acetate gradient. The resulting solid was recrystallized from ethanol to afford 1.8 grams of the desired product as a white solid. 1H NMR (CDCl3/D2O) delta 6.55-6.95 (m, 6H), 4.5 (t, 4H), 3.15 (t, 4H).

Reference： [1]Patent: EP1801105,2007,A1 .Location in patent: Page/Page column 11-12

10
[ 42933-43-7 ]
5-diazonium-2,3-dihydrobenzofuran tetrafluoroborate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With hydrogenchloride; tetrafluoroboric acid; sodium nitrite; In tetrahydrofuran; water; at -15℃; for 0.5h;	To a solution of 8.2 g (60.66 mmol) of <strong>[42933-43-7]2,3-dihydrobenzofuran-5-ylamine</strong> in 250 mL of THF was added 6 mL of concentrated aqueous HC1 in several portions. To the resulting white precipitate was added 11 mL of tetrafluoroboric acid dropwise. The mixture was then chilled (-15C) and 4.7 g (68.12 mmol) of sodium nitrite in 20 mL of water was added dropwise. The suspension turned deep gray, became homogenous and then a precipitate formed. The mixture was stirred for 30 minutes at-15C and then the solid was collected by filtration washing with cold water, cold ethanol, and cold ether. The solid was dried by pulling vacuum through the filter cake to afford 9.7 g (68%) of 5-diazonium-2, 3-dihydrobenzofuran tetrafluoroborate salt which was used without further purification.

Reference： [1]Patent: WO2003/82787,2003,A1 .Location in patent: Page/Page column 139

11
[ 75-36-5 ]
[ 42933-43-7 ]
[ 81926-25-2 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 4161 - 4172

12
[ 42933-43-7 ]
[ 245762-35-0 ]

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 6681 - 6698
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 5579 - 5601

13
[ 496-16-2 ]
[ 42933-43-7 ]

Reference： [1]ACS Catalysis,2016,vol. 6,p. 8162 - 8165
[2]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 6430 - 6446
[3]Patent: EP2532665,2012,A1
[4]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 3821 - 3830
[5]Journal of Medicinal Chemistry,2014,vol. 57,p. 5579 - 5601
[6]European Journal of Medicinal Chemistry,2019,vol. 182

14
[ 407-25-0 ]
[ 42933-43-7 ]
[ 632352-68-2 ]

Yield	Reaction Conditions	Operation in experiment
98%	With triethylamine; In dichloromethane; at 0 - 20℃; for 2h;	To a cooled mixture of 22 (4.51 g, 33.4 mmol) and Et3N (6.1 mL, 43.4 mmol) in CH2Cl2 (40 mL) was added trifluoroacetic anhydride (6.2 mL, 43.4 mmol) at 0 °C. After stirring at room temperature for 2 h, the reaction mixture was added into aqueous NH4Cl and extracted with EtOAc. The extract was washed with brine, dried and concentrated to provide 23 (7.1 g, 98percent) as white powder; 1H NMR (CDCl3) delta: 3.23 (2H, t, J = 8.7 Hz), 4.60 (2H, t, J = 8.7 Hz), 6.76 (1H, d, J = 8.1 Hz), 7.12 (1H, dd, J = 8.7, 2.4 Hz), 7.51 (1H, m), 7.65-7.80 (1H, m); Anal. Calcd for C10H8NO2F: C, 51.96; H, 3.49; N, 6.06. Found: C, 52.13; H, 3.39; N, 6.38.