Sodium hydride → HCID 75066246, compound

Participants

Reaction Steps

NaH (57 mg, 1.42 mmol, 60% in oil) was added to a solution of bromide 180 (450 mg, 1.18 mmol) in DMF (5 mL) at 0° C. 1,3-Dichloropropene (260 mg, 2.37 mmol) was added and the mixture was allowed to warm to room temperature over 1 h, then concentrated under reduced pressure CH2Cl2 and water were added and the organic phase was washed with water (×2), brine (×2), dried, and filtered through silica gel to give methyl 8-bromo-7-[(tert-butoxycarbonyl)(3-chloro-2-propen-1-yl)amino]-2-naphthoate (181) (520 mg, 97%) as a yellow oil; 1H NMR (CDCl3) (mixture of rotamers and E and Z forms) δ 9.07 (s, 10H), 8.18-8.08 (m, 1H), 7.93-7.78 (m, 2H), 7.42-7.32 (m, 1H), 6.15-5.98 (m, 2H), 4.01 (s, 3H), 4.63-4.48 (m, 2H), 1.26, 1.24 (2 s, 9H). HRMS (FAB) calcd. for C20H2179Br35ClNO4 (MH+) m/z 454.0421, found 454.0421.

Provenance & Evidence