Bromine → HCID 66696590, compound

Participants

Reaction Steps

A solution of Example 5A (6.46 g, 27.9 mmol) in tetrahydrofuran (48 mL) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (36 mL) was cooled to −78° C., and then treated slowly with lithium bis(trimethylsilyl)amide (1M in tetrahydrofuran, 34 mL, 34 mmol). The reaction was stirred for 1 hour and then treated dropwise with bromine (1.43 ml, 27.9 mmol). The reaction stirred for another hour at −78° C., and then was poured into 900 mL ether and 270 mL 10% Na2SO3 solution. The phases were separated, and the organic layer was washed with brine, dried over Na2SO4, filtered, and evaporated. The crude material was purified by chromatography (5 to 20% ethyl acetate-hexane) to afford the title compound as a yellow oil (4.58 g, 53% yield). 1H NMR (300 MHz, DMSO-d6) δ 8.74 (s, 1H), 8.02 (m, 2H), 7.81 (m, 1H). MS (DCI+) m/z 312 (M+H)+.

Provenance & Evidence