1H-Pyrrolo(2,3-b)pyridine → (6-Bromo-pyridin-3-yl)-(1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone

HRID 1256759Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N:8]=2)[CH:3]=[CH:2]1.[Br:10][C:11]1[CH:19]=[CH:18][C:14]([C:15](Cl)=[O:16])=[CH:13][N:12]=1.[Cl-].[Cl-].[Cl-].[Al+3]>ClCCl>[Br:10][C:11]1[N:12]=[CH:13][C:14]([C:15]([C:3]2[C:4]3[C:9](=[N:8][CH:7]=[CH:6][CH:5]=3)[NH:1][CH:2]=2)=[O:16])=[CH:18][CH:19]=1

Participants

Conditions

Temperature: -10 °C

Procedure

To a solution of 1H-Pyrrolo[2,3-b]pyridine (1, 1.2 g, 0.010 mol) in dichloromethane (50 mL) was added 6-bromo-nicotinoyl chloride (86, 2.6 g, 0.012 mol) at −10° C. After the solution turned clear, aluminum trichloride (10.2 g, 0.0765 mol) was added in one portion with vigorous stirring. The reaction mixture was stirred at −10° C. for 30 minutes, then was allowed to warm to room temperature and stirred at room temperature overnight. The reaction was quenched with ice water and neutralized with sodium bicarbonate. The solution was extracted with dichloromethane, washed with brine, and dried over sodium sulfate. After removal of solvent, the residue was purified by silica gel column chromatography eluting with methanol in dichloromethane to provide the compound as a white solid (87, 0.35 g, 11%).

Workup

temperatureto warm to room temperature
stirringstirred at room temperature overnight
customThe reaction was quenched with ice water and neutralized with sodium bicarbonate
extractionThe solution was extracted with dichloromethane
washwashed with brine
dry with materialdried over sodium sulfate
customAfter removal of solvent
customthe residue was purified by silica gel column chromatography
washeluting with methanol in dichloromethane

Sources & evidence

ORD record: ord-5673c4bfc44c43cc813be1c6de4a57de
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461169B2

Reaction notes

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