Stannous chloride dihydrate → HCID 86677530, compound

Participants

Reaction Conditions

Reaction Steps

A stirring mixture of 5-(3-methoxy-3-(trifluoromethyl)cyclobutyl)-3-(4-methyl-3-nitrophenyl)-1,2,4-oxadiazole (124) (40 mg, 0.112 mmol) and tin (II) chloride dihydrate (101 mg, 0.448 mmol) in ethanol (2 mL) was heated at 65° C. for 2 hours. The reaction was cooled to room temperature and the pH was adjusted between 8-10 with saturated sodium bicarbonate. The slurry was filtered and washed with aqueous ethanol. The solvent was partially reduced and the crude product was extracted with ethyl acetate. The organic was washed with 1× water and dried over anhydrous sodium sulfate. The crude product was purified by silica chromatography to yield 5-(5-(3-methoxy-3-(trifluoromethyl)cyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylaniline (125). 1H NMR (400 MHz, d6-DMSO) δ 10.24 (s, 1H), 10.13 (s, 1H), 8.70 (s, 1H), 8.08 (d, J=1.6 Hz, 1H), 7.95 (dd, J=2.0, 9.6 Hz, 1H), 7.88-7.84 (m, 2H), 7.52 (d, J=8.4 Hz, 1H), 3.92-3.84 (m, 1H), 3.24-3.02 (m, 4H), 2.64 (s, 3H), 2.38 (s, 3H). MS m/z 433.16 (M+1)+.

Provenance & Evidence