2-(6-bromo-1H-pyrrolo[2,3-b]pyridin-1-yl)(phenyl)methanone → 6-Bromo-7-azaindole
Reaction equation
[Br:1][C:2]1[N:7]=[C:6]2[N:8](C3C=CC=CC=3C=O)[CH:9]=[CH:10][C:5]2=[CH:4][CH:3]=1>O1CCOCC1.[OH-].[K+]>[Br:1][C:2]1[N:7]=[C:6]2[NH:8][CH:9]=[CH:10][C:5]2=[CH:4][CH:3]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
(6-bromo-1H-pyrrolo[2,3-b]pyridin-1-yl)(phenyl)methanone 155 was dissolved in 20 mL of dioxane and 20 mL of 2M KOH (aq). This was stirred at ambient temperature until analysis indicated all of the starting material had been consumed (2 to 4 hours). The reaction was diluted with 50 mL of ethyl acetate and washed with 2×25 mL of NaHCO3 (aq. satd.) and 25 mL of brine. The organic layer was dried with sodium sulfate, evaporated and purified by column chromatography. Combined steps 2 and 3 gave approximately 65% overall yield.
Workup
- customhad been consumed (2 to 4 hours)
- additionThe reaction was diluted with 50 mL of ethyl acetate
- washwashed with 2×25 mL of NaHCO3 (aq. satd.) and 25 mL of brine
- dry with materialThe organic layer was dried with sodium sulfate
- customevaporated
- custompurified by column chromatography
- customgave approximately 65% overall yield
Sources & evidence
- ORD record
- ord-713df9f7ab6c43edb73d1bd9ca0686f7
- Source dataset
- uspto-grants-2011_01
- Patent number
- US07872018B2
Reaction notes
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