Ethyl Bromide → 1-Ethyl-5-methoxy-1h-pyrrolo[2,3-c]pyridine-2-carboxylic acid
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[CH:11]=[C:10]([C:12]([OH:14])=[O:13])[NH:9][C:6]2=[CH:7][N:8]=1.[OH-].[K+].Br[CH2:18][CH3:19]>CS(C)=O>[CH2:18]([N:9]1[C:6]2=[CH:7][N:8]=[C:3]([O:2][CH3:1])[CH:4]=[C:5]2[CH:11]=[C:10]1[C:12]([OH:14])=[O:13])[CH3:19]Participants
Procedure
To a solution of 5-methoxy-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (500 mg, 2.60 mmol) (available from, for example, Activate Scientific GmbH) in dimethyl sulfoxide (DMSO) (5 mL) was added potassium hydroxide (438 mg, 7.81 mmol) and bromoethane (0.427 mL, 5.72 mmol). The reaction was stirred at room temperature for 18 h before adding further potassium hydroxide (120 mg) and bromoethane (0.13 ml). After stirring for a further 4 h, the reaction mixture was stood under nitrogen for ca. 66 h. It was then partitioned between water and diethyl ether. The layers were separated and the aqueous was washed with diethyl ether. The aqueous was acidified to pH=3, and was extracted with ethyl acetate (twice). The combined ethyl acetate extracts were washed with water and concentrated in vacuo to yield the title compound as a pale beige solid (148 mg).
Workup
- stirringAfter stirring for a further 4 h
- waitthe reaction mixture was stood under nitrogen for ca. 66 h
- customIt was then partitioned between water and diethyl ether
- customThe layers were separated
- washthe aqueous was washed with diethyl ether
- extractionwas extracted with ethyl acetate (twice)
- washThe combined ethyl acetate extracts were washed with water
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-73e3ca2d23d445fd8ee9b63c3a4482a2
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09127003B2
Reaction notes
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