Acetonitrile → 5-Bromo-4,6-difluoro-1H-indole-3-carbaldehyde
Reaction equation
[Br:1][C:2]1[C:3]([F:12])=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[NH:7][CH:6]=[CH:5]2.[OH-:13].[Na+].[C:15](#N)C>>[Br:1][C:2]1[C:3]([F:12])=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[NH:7][CH:6]=[C:5]2[CH:15]=[O:13]Participants
Procedure
To a solution of 5-bromo-4,6-difluoro-1H-indole (1.29 g, 5.56 mmol) in acetonitrile (7.0 mL) was added N,N-dimethylformiminium chloride (1.07 g, 8.34 mmol). The reaction mixture was stirred at room temperature for 45 minutes. To the reaction mixture was added 1N NaOH (15 mL, 15 mmol). The resulting mixture was heated to 100° C. for 60 minutes, cooled to 0° C. and the resulting solid was collected via filtration, washed with water, and air-dried with vacuum to provide 900 mg of the title compound. An additional crop of solids formed in the filtrate, was collected, and dried to provide an additional 371 mg of the title compound for a total of 1.271 g (88% yield). MS (ES+) 260.3 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ 12.58 (br. s, 1 H), 9.93 (d, J=3.90 Hz, 2 H), 8.34 (s, 2 H), 7.39 (dd, J=8.49, 1.07 Hz, 1 H).
Workup
- temperatureThe resulting mixture was heated to 100° C. for 60 minutes
- temperaturecooled to 0° C.
- filtrationthe resulting solid was collected via filtration
- washwashed with water
- customair-dried with vacuum
Sources & evidence
- ORD record
- ord-cdbd59b4a3bf4199a354ed83d74a4e46
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09394285B2
Reaction notes
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