1H-Indole-2-carboxylic acid, 1-methyl- → N-[4-(5-Ethyl-3-pyridin-3-yl-pyrazol-1-yl)phenyl]-1-methylindole-2-carboxamide

Participants

Reaction Steps

A DMF (2 mL) solution of 3-(3-pyridyl)-5-ethyl-1-(4′-aminophenyl)pyrazole (264 mg, 1 mmol), N-methylindole-2-carboxylic acid (192.5 mg, 1.1 mmol), PyBOP (570 mg, 1.1 mmol) and N,N-diisopropylethylamine (0.21 mL, 1.2 mmol) was stirred at room temperature. for 18 hr. The reaction mixture was poured into crushed ice, and extracted with methylene chloride (3×50 mL). The combined extracts were washed with water, dried over anhydrous sodium sulfate, and the solvent was evaporated. Chromatography of the residue over silica gel (4% methanol/methylene chloride) followed by preparative TLC (silica gel, developer 5% methanol/methylene chloride) gave the title compound as a light, cream colored solid, m.p. 178-179° C. 1H NMR (DMSO-d6) δ 1.2 (3H, t, J=7.5), 2.73 (2H, q, J=7.5 Hz), 4.05 (3H, s), 6.93 (1H, s), 7.16 (1H, t, J=7.5), 7.34 (1H, t, J=7.5), 7.37 (1H, s), 7.44-7.48 (1H, dd, J=3.1 & 4.7 Hz), 7.57-7.61 (3H, m), 7.74 (1H, d, J=7.9 Hz), 7.98 (2H, d, J=8.8 Hz), 8.2-8.22 (1H, m), 8.53-8.54 (1H, m), 9.07 (1H, d, J=1.8 Hz), 10.56 (1H, s).

Provenance & Evidence