1,2-Dichloroethane → tert-butyl (5-((6-bromo-1-isopropyl-3-methyl-1H-indole-4-carboxamido)methyl)-6-methoxy-4-methylpyridin-2-yl)carbamate

Participants

Reaction Steps

To a stirred solution of tert-butyl (5-(aminomethyl)-6-methoxy-4-methylpyridin-2-yl)carbamate (0.40 g, 1.496 mmol), 6-bromo-1-isopropyl-3-methyl-1H-indole-4-carboxylic acid (0.44 g, 1.486 mmol), and HOAt (0.21 g, 1.543 mmol) in DMF (25 mL) was added EDC free base (0.25 g, 1.610 mmol). The reaction was stirred at RT overnight then evaporated to dryness under vacuum. The remaining was purified by silica gel chromatography (Analogix, SF25-60 g, 0 to 30% EtOAc in hexanes) to give the product tert-butyl (5-((6-bromo-1-isopropyl-3-methyl-1H-indole-4-carboxamido)methyl)-6-methoxy-4-methylpyridin-2-yl)carbamate (0.81 g, 1.485 mmol, 99% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ=9.42 (s, 1 H), 8.41 (t, J=4.8 Hz, 1 H), 7.77 (d, J=1.5 Hz, 1 H), 7.33 (s, 1 H), 7.21 (s, 1 H), 6.99 (d, J=1.8 Hz, 1 H), 4.40 (d, J=5.1 Hz, 2 H), 3.81 (s, 3 H), 2.35 (s, 3 H), 2.10 (d, J=1.0 Hz, 3 H), 1.47 (s, 9 H), 1.38 (d, J=6.6 Hz, 6 H). MS(ES)+m/e 545.2 [M+H]+.

Provenance & Evidence