Sodium hydride → HCID 117728141, compound

Participants

Reaction Steps

To a solution of 7-bromo-4-methyl-2H-benzo[e][1,2,4]thiadiazin-3(4H)-one 1,1-dioxide (510 mg, 1.7 mmol) in DMF (10 mL), 60% NaH (69 mg, 1.7 mmol) was added in portions at 0° C. The resulting mixture was stirred at rt for 10 min and p-methoxybenzyl chloride (0.25 mL, 1.7 mmol) was added. The resulting mixture was stirred at 70° C. for 5 h, cooled to rt and poured over ice. The resulting compound was extracted with EtOAc (3×20 mL). The combined EtOAc layers were dried over Na2SO4, filtered, and concentrated. The residue obtained was purified by flash column chromatography on silica gel (0-100% EtOAc/heptanes) to obtain compound 40a. 1H-NMR (400 MHz, CDCl3) δ (ppm): 8.01 (d, J=2.0 Hz, 1H), 7.74 (dd, J=8.8, 2.3 Hz, 1H), 7.40 (d, J=8.6 Hz, 2H), 7.10 (d, J=8.6 Hz, 1H), 6.83 (d, J=8.6 Hz, 2H), 4.99 (s, 2H), 3.77 (s, 3H).

Provenance & Evidence