475039-81-7

98600-34-1

475039-81-7

General procedure for the synthesis of 4-bromo-3-methyl-1H-indole from 4-bromoindole-3-carboxaldehyde: Lithium aluminum hydride (LAH, 1.0 M tetrahydrofuran (THF) solution, 5.75 mL, 5.75 mmol) was added slowly and dropwise to refluxed 4-bromo-1H-indole-3-carboxaldehyde (644 mg, 2.87 mmol) in anhydrous THF (20 mL); Intermediate 27) solution. The reaction mixture was refluxed for 1 h and cooled to room temperature. The reaction was quenched sequentially by the addition of water (220 μL), 15% aqueous sodium hydroxide solution (220 μL) and water (650 μL). The resulting precipitate was collected by filtration, the filtrate was concentrated, and the residue was extracted with aqueous sodium hydroxide (10 mL) and dichloromethane (2 x 10 mL). The organic layer was combined with a previous batch (from 4-bromo-1H-indole-3-carboxaldehyde, 100 mg, 0.45 mmol; starting with Intermediate 27) of this intermediate, dried and concentrated to give the title compound (556 mg, 80% yield) as a light brown oil. Mass spectrometry (ESI+) analysis showed the molecular ion peak m/z 210 (M+H)+ for C9H8BrN.