Sodium hydride → HCID 45103348, compound

Participants

Reaction Steps

Sodium hydride (1.08 g, 60% in mineral oil) was added to a stirred solution of (2,4-dimethoxyphenyl)methanol (4.54 g) dissolved in tetrahydrofuran (150 ml) over a period of 5 minutes at 0° C. After 30 minutes, 3-(4-fluoro-1,3-benzoxazol-2-yl)pyridin-2-amine (1.547 g) was added and the mixture was heated to reflux for 16 hours. The THF was evaporated, water was added and the resultant solid was filtered and washed with water. The solid was then triturated with diethyl ether and dried with phosphorus pentoxide under reduced pressure to afford 3-[4-[(2,4-dimethoxyphenyl)methoxy]-1,3-benzoxazol-2-yl]pyridin-2-amine (2.32 g) as a solid. NMR Spectrum: (CDCl3) 3.82 (s, 3H), 3.86 (s, 3H), 5.41 (s, 2H), 6.50 (dd, 1H), 6.51 (s, 1H), 6.75 (dd, 1H), 6.91 (d, 1H), 6.96 (bs, 2H), 7.17 (d, 1H), 7.24 (d, 1H), 7.41 (d, 1H), 8.20 (dd, 1H), 8.29 (dd, 1H); Mass spectrum: M+H+ 378

Provenance & Evidence