Ammonia → HCID 10354834, compound

Participants

Reaction Steps

At −20° C. stir a solution of 3-(pyridin-4-ylamino)-1H-indole-2-carboxylic acid (1.26 g, 3.0 mmol) in DMF (12 mL) and add BOP (1.32 g, 3.0 mmol) and then diisopropylethylamine (0.8 mL, 4.5 mmol). Stir the reaction for 0.25 h and add a solution of 7M NH3 in MeOH (0.43 mL, 3.0 mmol). Allow the reaction to stir at room temperature overnight and add EtOAc. Wash the organic solution with aqueous NaHCO3, brine and dry over MgSO4. Filter and concentrate the filtrate under vacuum to obtain a solid. Recrystallize the solid from EtOAc to obtain 0.425 g of the title compound as a yellow solid: MS 253(M+H); m.p. 230° C. (decomposition); TLC (silica gel, dichloromethane/MeOH/NH4OH, 8:2:0.1 v/v), Rf=0.39.

Provenance & Evidence