Methanol → 6-Bromo-7-fluoro-2'-methyl-2-phenyl-2'h-spiro[chroman-4,5'-[1,2,4]oxadiazol]-3'-amine

Participants

Reaction Steps

To a solution of N-methyl-hydroxylamine hydrochloride (35 mg, 0.355 mmol) in MeOH (5 mL) was added MeONa (0.07 mL, 25% (Wt.) in MeOH), followed by N-(6-bromo-7-fluoro-2-phenylchroman-4-ylidene)cyanamide (122 mg, 0.355 mmol). After stirred for 10 minutes, the solvent was removed in vacuo. The residue was purified by preparative TLC to give 6-bromo-7-fluoro-2′-methyl-2-phenyl-2′H-spiro[chroman-4,5′-[1,2,4]oxadiazol]-3′-amine (30 mg, 30%). 1H-NHR (MeOD): 2.18 (m, 1H), 2.33 (m, 1H), 3.08 (d, 3H), 5.28 (m, 1H), 6.75 (m, 1H), 7.38 (m, 5H), 7.61 (m, 1H).

Provenance & Evidence