2-Methyl-2-butene → 1-Methyl-1H-pyrrolo[2,3-c]pyridine-3-carboxylic acid

Participants

Reaction Steps

1-methyl-1H-pyrrolo[2,3-c]pyridine-3-carbaldehyde (WO 05066132) (6.5 g, 40.6 mmol) was dissolved in a mixture of THF (120 mL) and tert-butyl alcohol (40 mL) under nitrogen. 2-Methyl-2-butene (120 mL of a 2M solution in THF, 46 mmol) was added followed by a solution of NaClO2 (11.0 g, 122 mmol) and NaH2PO4 (21.9 g, 183 mmol) in water (30 mL). The reaction mixture was stirred at room temperature overnight under nitrogen. The reaction mixture was concentrated in vacuo to remove organic solvents, and the residue was filtered. The precipitate contained the title compound as a white solid in 57% yield, 4.1 g.

Provenance & Evidence