2,4-Difluorobenzylamine → HCID 22051191, compound

Participants

Reaction Steps

The product from Step 2 (0.5 g, 2.28 mmol) and 2,4-difluoro benzylamine (4 mL, 33.6 mmol) were combined in a nitrogen flushed culture tube. The tube was capped and heated at 180 C for 24 h. The excess amine was distilled in vacuo and the residue was chromatographed on silica (95:5 ethyl acetate: methanol). The final compound was isolated as a light yellow solid (0.16 g, 36%). 1H NMR (400 MHz, CD3OD) δ 7.33 (m, 3H), 7.03 (d, J=8 Hz, 1H), 6.96 (m, 3H), 6.95 (m, 1H), 5.97 (dd, J=3.2 and 8.0 Hz, 1H), 5.48 (d, J=2.56 Hz, 1H), 5.02 (s, 2H), 4.33 (s, 2H) ppm. 19F NMR (400 MHz, CD3OD) δ−113.88 (1 F), −115.33 (1 F), −116.78 (1 F) ppm. ES-HRMS m/z 345.1221 (M+H calcd for C19H17F3N2O requires 345.1209). Step 4 Preparation of 3-bromo-4-[(2,4-difluorobenzyl)amino]-1-(3-fluorobenzyl)pyridin-2(1H)-one

Provenance & Evidence