Triethylamine → HCID 57893547, compound

Participants

Reaction Conditions

Reaction Steps

7-Chloro-N-(2-pyridinylmethyl)-1H-pyrrolo[2,3-c]pyridine-2-carboxamide (Example 4) (0.06 g, 0.21 mmol) in N,N-dimethylformamide (4.2 mL) was warmed to 60° C. under a nitrogen atmosphere. To the stirring solution were added triethylamine (0.06 mL, 0.43 mmol) and palladium dichloride (spatula tip, catalytic amount), and the reaction mixture was placed under a hydrogen atmosphere. The formation of palladium black was observed within 15 min. After stirring at 60° C. for 2 h, the heating bath was removed and the reaction mixture was stirred at room temperature overnight under a hydrogen atmosphere. The crude reaction mixture was filtered through a pad of diatomaceous earth, and the filtrate was concentrated. The residue was dissolved in ethyl acetate and washed with saturated NH4Cl and saturated NaCl, and dried over Na2SO4. Filtration and concentration provided N-(2-pyridinylmethyl)-1H-pyrrolo[2,3-c]pyridine-2-carboxamide (0.015 g, 25%) as an off-white solid: mp 230-236 C; 1H NMR (300 MHz, CD3OD) δ4.73 (2H, s), 7.20 (1H, s), 7.31-7.35 (1H, m), 7.46 (1H, d, J=7.9 Hz), 7.67 (1H, d, J=5.6 Hz), 7.79-7.83 (1H, m), 8.12 (1H, d, J=5.6 Hz), 8.50-8.52 (1H, m), 8.79 (1H, s); ESI MS m/z 253 [C14H12N4O+H]+; HPLC (Method A) 95.5% (AUC), tR=16.7 min.

Provenance & Evidence