Water → 7-Chloro-N-(phenylmethyl)-1H-pyrrolo[2,3-c]pyridine-2-carboxamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 7-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (Reference Example 1) (0.10 g, 0.51 mmol) and 1,1′-carbonyldiimidazole (0.09 g, 0.53 mmol) in N,N-dimethylformamide (3.4 mL) was stirred at 50° C. for 1 h. To the stirring solution was added benzylamine (0.11 mL, 1.02 mmol) and the reaction mixture was stirred at 65° C. until the reaction was complete by TLC analysis. The crude reaction mixture was poured into rapidly stirring water, and extracted with ethyl acetate (3×). The combined organic extracts were washed with water (3×) and saturated NH4Cl, and dried over Na2SO4. The organic extract was filtered and concentrated to provide N-benzyl-7-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxamide (0.04 g, 0.14 mmol, 27%) as an off-white solid: mp 217-220° C.; 1H NMR (300 MHz, CDCl3) δ4.70 (2H, d, J=5.7 Hz), 6.45-6.61 (1H, m), 6.85 (1H, s), 7.31-7.39 (5H, m), 7.47 (1H, d, J=5.7 Hz), 8.06 (1H, d, J=5.7 Hz), 9.55 (1H, br s); APCI MS m/z 286 [C15H12ClN3O+H]+; HPLC (Method A) >99% (AUC), tR=16.3 min.

Provenance & Evidence