Triethylamine → HCID 90466565, compound

Participants

Reaction Steps

See FIG. 16(b). To a stirred solution of 1-(5-fluoro-2-methoxybenzyl)-7-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid (0.22 g, 0.000699 moles) in dichloromethane (10 mL) were added 2-fluoroethan-1-amine (0.06 g, 0.000836 moles), triethylamine (0.29 ml, 0.002 moles) and T3P (1.32 ml, 0.002 moles) and the mixture was stirred for 16 h at room temperature. The reaction mixture was poured in to water and extracted with dichloromethane. The combined organic layer was washed with water, brine and the solvent was evaporated under reduced pressure. The crude was purified by flash column chromatography using 50% ethyl acetate in hexane to afford N-(cyclopropylmethyl)-1-(5-fluoro-2-methoxybenzyl)-7-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide as a off-white solid. Yield-24%. ES+MS m/z: 368. 1H NMR (400 MHz, DMSO-d6) δ ppm: 0.22-0.24 (m, 2H ), 0.48-0.50 (m, 2H ), 1.05-1.09 (m, 1H ), 2.44 (s, 3H ), 3.28 (t, 2H , J=6.2 Hz), 3.86 (s, 3H ), 5.63 (s, 2H ), 5.97-6.00 (m, 1H ), 7.03-7.04 (m, 1H ), 7.12-7.14 (m, 2H ), 8.22 (s, 1H ), 8.37 (d, 1H , J=4.8 Hz), 9.01 (t, 1H , J=5.6 Hz).

Provenance & Evidence