Diethyl Ether → HCID 58525647, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 8-fluoro-3-methyl-2-oxazol-2-ylmethyl-2H-isoquinolin-1-one (271 mg, 1.05 mmol) and N-bromosuccinimide (192 mg, 1.08 mmol) in N,N-dimethylformamide (4.8 mL) was stirred at 50° C. for 60 minutes. The reaction mixture was poured into diethyl ether (50 mL) and ethyl acetate (20 mL). A white solid precipitated, which was removed by filtration. The filtrate was washed with diluted brine (water:sat. NaCl(aq.)=1:1; 4×20 mL), dried over MgSO4 and evaporated to give a 321 mg of a solid (yield 90%), which was used in the next step without further purification. LC-MS (m/z) 337.3&339.4 (MH+), tR=1.1. 1H NMR (CDCl3, 500 MHz, TMS=0 ppm): 2.75 (s, 3H, Me), 5.52 (s, 2H, CH2), 7.07 (s (unres. d, J<1 Hz), 1H, oxazol), 7.16 (dd, J=8.1 Hz, J=11.1 Hz, 1H, C7-H), 7.62 (s (unres. d, J<1 Hz), 1H, oxazole), 7.66 (dt, J(t)=8.1 Hz, J(HF)=4.9 Hz, 1H, C6-H), 7.78 (d, J=8.2 Hz, 1H, C5-H).

Provenance & Evidence