Dimethylformamide → Methyl 3-formyl-1H-indole-5-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of anhydrous DMF (12 mL) under argon at 0° C. was added POCl3 (446 μL, 4.9 mmol). The reaction mixture has been stirred at 0° C. for 5 min. The methyl 1H-indole-5-carboxylate (854 mg, 4.9 mmol) in solution in DMF was added dropwise. The resulting mixture has been heated at 120° C. for 1 h. Then, it is quenched by addition of a saturated solution of NaHCO3 (2 mL). The mixture is diluted with DCM, washed with brine, dried over MgSO4 and concentrated. The product is precipitated in hexane/diethyl ether (1/1) to yield a red powder (896 mg, 4.4 mmol, 91%). ESI-MS (m/z): 204 [M+H]+.

Provenance & Evidence