6-Bromo-1H-pyrrolo[3,2-b]pyridine
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![6-Bromo-1H-pyrrolo[3,2-b]pyridine structure](https://file.echemi.com/fileManage/upload/canonicalSmiles/20220811/abf20c93502440edbb7478d9edfd1ce2.png "6-Bromo-1H-pyrrolo[3,2-b]pyridine")
6-Bromo-1H-pyrrolo[3,2-b]pyridine
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CAS No:
944937-53-5
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Formula:
C7H5BrN2
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Chemical Name:
6-Bromo-1H-pyrrolo[3,2-b]pyridine
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Synonyms:
1H-Pyrrolo[3,2-b]pyridine,6-bromo-;6-Bromo-1H-pyrrolo[3,2-b]pyridine
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CAS No:
Safety Information
IRRITANT
NONH for all modes of transport
3
22-36/37/38
26
Xi,Xn
P261-P280-P305 + P351 + P338
H302-H315-H318-H335
|Danger|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P330, P332+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 40 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
6-Bromo-1H-pyrrolo[3,2-b]pyridine Use and Manufacturing
Preparative Step 1: 6-bromo-lH-pyrrolo[3, 2-b]pyridine To a solution of 5-bromo-2-methyl-3-nitropyridine (1.58 g, 7.28 mmol) in N, N-dimethylmethanamide (10 mL) was added N, N-dimethylformamide dimethyl acetal (1.65 mL, 12.37 mmol). The reaction mixture was heated to 100 °C for 1 h and subsequently concentrated to dryness in vacuo. The residue was dissolved in acetic acid (20 mL), and iron powder (1.22 g, 21.8 mmol) was added. The reaction mixture was purged with nitrogen for 2 min and heated to 100 °C for 20 h. After cooling down, the reaction mixture was diluted with methanol and filtered. The precipitate was washed with methanol. The mother liquid and the washing were concentrated to dryness in vacuo. The resulting viscous mass was diluted with aqueous sodium carbonate and extracted with ethyl acetate (2 x 60 mL). The combined organic layers were dried over sodium sulfate and concentrated to dryness in vacuo. The resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 25percent ethyl acetate in hexane) affording 6-bromo-lH-pyrrolo[3, 2-b]pyridine (820 mg, 60percent): Step 4 - Synthesis of 6-brom -lH-pyrrolo[3, 2-b]pyridineA mixture of 2-(5-bromo-3-nitropyridin-2-yl)-N, N-dimethylethenamine (1.0 g, 3.7 mmol) and Fe (1.8 g, 32.2 mmol) in AcOH (10 mL) was heated at 100 °C overnight. After the reaction mixture was filtrated, the filtrate was concentrated, the resulting residue was purified using column chromatography eluted with PE : EtOAc = 5 : 1 to provide 6-bromo-lH-pyrrolo[3, 2-b]pyridine (24 mg, yield: 33.3percent).Step 4 - Synthesis of 6-brom -lH-pyrrolo[3, 2-bJpyridineA mixture of 2-(5-bromo-3-nitropyridin-2-yl)-N, N-dimethylethenamine (1.0 g, 3.7 mmol) and Fe (1.8 g, 32.2 mmol) in AcOH (10 mL) was heated at 100 °C overnight. After the reaction mixture was filtrated, the filtrate was concentrated, the resulting residue was purified using column chromatography eluted with PE : EtOAc = 5 : 1 to provide 6-bromo-lH-pyrrolo[3, 2-b]pyridine (24 mg, yield: 33.3percent). (M+H)
6-Bromo-1H-pyrrolo[3,2-b]pyridine is used in the preparation of benzofuran and pyridine compounds in the treatment of viral diseases, respiratory illnesses, inflammatory diseases.
Computed Properties
Molecular Weight:197.03
XLogP3:1.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:195.96361
Monoisotopic Mass:195.96361
Topological Polar Surface Area:28.7
Heavy Atom Count:10
Complexity:129
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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6-Bromo-1H-pyrrolo[3,2-b]pyridine
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