Triethylsilane → HCID 66716896, compound

Participants

Reaction Conditions

Reaction Steps

In a 20 mL scintillation vial was added 6-bromo-2-methyl-8-propionyl-2H-benzo[b][1,4]oxazin-3(41)-one 358B (517 mg, 1.734 mmol) and triethylsilane (0.554 mL, 3.47 mmol) in TFA (7.0 mL) and stirred at 40° C. for 4 h. The reaction was concentrated in vacuo and the residue was taken up in EtOAc (25 mL), washed with sat aq NaHCO3 and brine, dried over MgSO4, and concentrated in vacuo. The residue was purified via ISCO flash chromatography (0-100% EtOAc in hexanes; 40 g column). Collected fractions gave the title compound as a yellow solid (249 mg, 0.876 mmol, 50.5% yield). 1H NMR (400 MHz, DMSO-d6): δ=10.69 (s, 1H), 6.98 (d, J=2.5 Hz, 1H), 6.87 (d, J=2.3 Hz, 1H), 4.65 (q, J=6.8 Hz, 1H), 1.48-1.58 (m, 2H), 1.38 (d, J=6.8 Hz, 5H), 0.87 ppm (t, J=7.3 Hz, 3H). ESI-MS: m/z 284.1 (M+H)+.

Provenance & Evidence