165669-35-2|7-Bromo-1H-pyrrolo[2,3-c]pyridine| Ambeed

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Quality Control of [ 165669-35-2 ] Purity: 97% SDS Specification

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Product Details of [ 165669-35-2 ]

CAS No. :	165669-35-2
Formula :	C₇H₅BrN₂
M.W :	197.03
SMILES Code :	BrC1=NC=CC2=C1NC=C2
MDL No. :	MFCD03839909
InChI Key :	HTQAZKOPQOXNHI-UHFFFAOYSA-N
Pubchem ID :	19696456

Safety of [ 165669-35-2 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H301-H315-H318-H335
Precautionary Statements:	P261-P280-P301+P310-P305+P351+P338
Class:	8(6.1)
UN#:	2923
Packing Group:	Ⅲ

Application In Synthesis of [ 165669-35-2 ]

* 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.

Downstream synthetic route of [ 165669-35-2 ]

[ 165669-35-2 ] Synthesis Path-Downstream 1~33

2
1H-pyrrolo[2,3-c]pyridine-7-amine [ No CAS ]
[ 165669-35-2 ]

Yield	Reaction Conditions	Operation in experiment
		This product was reacted and treated in a similar manner to that of Examples 1 and 2 to give 57 mg of the title compound. 1 H-NMR(DMSO-d6) δ(ppm): 6.93(1H, d, J=6.6 Hz), 7.45(1H, dd, J=6.6, 5.8 Hz), 7.53(1H, dd, J=8.0, 7.6 Hz), 7.61(1H, d, J=7.6 Hz), 7.73(1H, d, J=2.8 Hz), 7.85(1H, d, J=8.0 Hz), 7.96(1H, d, J=1.2 Hz), 11.90-12.10(1H, m), 12.72(1H, br s)

References: [1]Patent: US5721246,1998,A .

3
[ 19755-53-4 ]
aqueous concentrated ammonia [ No CAS ]
[ 165669-35-2 ]
copper [ No CAS ]
1H-pyrrolo[2,3-c]pyridine-7-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	copper(I) chloride;	3-Chloro-N-(3-chloro-1H-pyrrolo[2,3-c]pyridine-7-yl)benzenesulfonamide To 84 ml of aqueous concentrated ammonia were added 600 mg (3.05 mmol) of <strong>[165669-35-2]7-bromo-1H-pyrrolo[2,3-c]pyridine</strong> synthesised from 2-bromo-3-nitropyridine in the same manner as in Production Example la, 194 mg of a copper powder and 603 mg of cuprous chloride. The mixture was heated in a sealed tube at 120 C. for 15 hours and then treated, to give 170 mg of 7-amino-1H-pyrrolo[2,3-c]pyridine.

References: [1]Patent: US2004/18192,2004,A1 .

4
[ 19755-53-4 ]
[ 1826-67-1 ]
[ 165669-35-2 ]

Yield	Reaction Conditions	Operation in experiment
60%	In tetrahydrofuran; at -78 - -40℃;	Example 1: Synthesis of [l-(4-methoxy-benzenesulfonyl)-lH-pyrrolo[2,3-c]pyridin-7-yi]- phenyl-amine (Compound 1); 7-Bromo-6-azaindole (2 in Scheme 1): A solution of 2-Bromo-3-nitropyridine (1 in Scheme 1, 2.0 g , 98% , 9.7 mmol) in dry TΗF(80 mL) was cooled to -78C. Excess vinylmagnesium bromide (1.0 M in THF, 40 mL , 40 mmol) was added. The reaction mixture was stirred at -40~-50C for Ih before it was quenched with saturated NaHCθ3 solution. The layers were separated and the aqueous layer was extracted with EtOAc (3 times). The combined organic layers were dried over MgSO4, the dried solution was filtered, and the filtrate was concentrated. The residue was purified by flash chromatography (EtOAc :«-hexane = 1:2) to afford 2 (1.1 g,60%).1H NMR (500 MHz, CDCl3): δ 6.66 (dd, IH, J= 2.9, 2.1 Hz), 7.43 (dd, IH, J= 2.9, 2.1Hz), 7.51 (d, IH, J= 5.2 Hz), 8.03 (d, IH, J= 5.3 Hz), 8.79 (br, IH).

References: [1]Patent: WO2011/19634,2011,A2 .Location in patent: Page/Page column 13.

5
[ 165669-35-2 ]
[ 98-68-0 ]
[ 1265023-89-9 ]

Yield	Reaction Conditions	Operation in experiment
97%	With tetra(n-butyl)ammonium hydrogensulfate; potassium hydroxide; In dichloromethane;	7-Bromo-l-(4-methoxy-benzenesulfonyl)-lH-pyrrolo[2,3-c]pyridine (3 in Scheme 1):; Potassium hydroxide (1.71 g, 30.45 mmol) and tetra-n-butylammonium hydrogen sulfate (0.345 g, 1.015 mmol) were added to a solution of 2 (2.0 g, 10.15 mmol) in dichloromethane (100 mL).The reaction mixture thus formed was stirred for 30 min. 4-Methoxysulfonyl chloride (4.2 g,20.3 mmol) was added slowly to the reaction mixture. After 1 h the mixture was quenched with water and extracted with CΗ2CI2 The combined organic layers were dried over MgSO4, the dried solution was filtered, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (EtOAc: w-hexane = 1: 1) to afford 3 (3.6 g, 97%).1H NMR (500 MHz, CDCl3): δ 3.84 (s, 3H), 6.72 (d, IH, J=3.7 Hz), 6.94 (d, 2H, J= 8.9Hz), 7.46 (d, IH, J =5.1 Hz), 7.77 (d, 2H, J= 8.9 Hz), 8.07 (d, IH, J=3.7 Hz), 8.12 (d, IH, J =5.2 Hz).

References: [1]Patent: WO2011/19634,2011,A2 .Location in patent: Page/Page column 13.
[2]Journal of Medicinal Chemistry,2013,vol. 56,p. 8008 - 8018.

6
[ 165669-35-2 ]
[ 1265022-42-1 ]

References: [1]Patent: WO2011/19634,2011,A2 .
[2]Journal of Medicinal Chemistry,2013,vol. 56,p. 8008 - 8018.

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[ 165669-35-2 ]
[ 1265022-24-9 ]

References: [1]Patent: WO2011/19634,2011,A2 .
[2]Journal of Medicinal Chemistry,2013,vol. 56,p. 8008 - 8018.

8
[ 165669-35-2 ]
[ 1503-98-6 ]
[ 1426255-06-2 ]

Yield	Reaction Conditions	Operation in experiment
36%	With caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene;tris-(dibenzylideneacetone)dipalladium(0); In toluene; at 120℃; for 8h;	To a solution of 7-bromo-1 H-pyrrolo[2,3-c]pyridine (500 mg, 2.53 mmol) in toluene were added tris (dibenzylidene acetone) dipalladium (1 16.20 mg, 0.126 mmol), Xantphos (32.98 mg, 0.057 mmol), cesium carbonate (896 mg, 2.75 mmol), and cyclobutanecarboxamide (251 mg, 2.96 mmol, Intermediate 4). The resulting reaction mixture was heated to 120 C and stirred for 8 hours. After cooling to room temperature a saturated aqueous sodium bicarbonate solution (20 mL) was added to the reaction mixture and extracted with ethyl acetate (3 x 50 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by silica gel (100-200) column chromatography to afford A/-(1 /-/-pyrrolo[2,3-c]pyhdin-7-yl) cyclopropane carboxamide (200 mg, 36 % yield).1H NMR (400 MHz, CHCI3-cf): δ 7.72 - 7.79 (m, 1 H), 7.45 - 7.54 (m, 1 H), 7.38 - 7.45 (m, 1 H), 6.58 - 6.63 (m, 1 H), 3.47 - 3.51 (m, 1 H), 2.29 - 2.51 (m, 2H), 1 .88 - 2.14 (m, 2H), 1 .21 - 1 .31 (m, 2H). MS: 216.56 (M+1 ).
36%	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In toluene; at 120℃; for 8h;	To a solution of <strong>[165669-35-2]7-bromo-1H-pyrrolo[2,3-c]pyridine</strong> (500 mg, 2.53 mmol) in toluene were added tris (dibenzylidene acetone) dipalladium (116.20 mg, 0.126 mmol), Xantphos (32.98 mg, 0.057 mmol), cesium carbonate (896 mg, 2.75 mmol), and cyclobutanecarboxamide (251 mg, 2.96 mmol, Intermediate 4).; The resulting reaction mixture was heated to 120 C. and stirred for 8 hours. After cooling to room temperature a saturated aqueous sodium bicarbonate solution (20 mL) was added to the reaction mixture and extracted with ethyl acetate (3*50 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by silica gel (100-200) column chromatography to afford N-(1H-pyrrolo[2,3-c]pyridin-7-yl)cyclopropane carboxamide (200 mg, 36% yield). 1H NMR (400 MHz, CHCl3-d): δ 7.72-7.79 (m, 1H), 7.45-7.54 (m, 1H), 7.38-7.45 (m, 1H), 6.58-6.63 (m, 1H), 3.47-3.51 (m, 1H), 2.29-2.51 (m, 2H), 1.88-2.14 (m, 2H), 1.21-1.31 (m, 2H). MS: 216.56 (M+1).

References: [1]Patent: WO2012/160464,2012,A1 .Location in patent: Page/Page column 60.
[2]Patent: US2014/155398,2014,A1 .Location in patent: Paragraph 0369.

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[ 19755-53-4 ]
[ 165669-35-2 ]