Sodium Carbonate → HCID 86677525, compound

Participants

Reaction Steps

Tert-butyl (5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)carbamate (36) (1.2 g, 3.3 mmol) was dissolved in TFA (10 mL) and stirred at room temperature for 15 minutes. Then TFA was removed under vacuum to give the residue which was neutralized by addition of 2M Na2CO3 solution (20 mL). The solution was extracted with EtOAc and the organic phase was dried over Na2SO4. Evaporation of solvent gave 5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylaniline (37) as a white solid (0.9 g, 100% yield), which was used without further purification. 1H NMR (400 MHz, d6-DMSO) δ 7.33 (d, J=1.2 Hz, 1H), 7.14 (dd, J=1.2, 7.6 Hz, 1H), 7.09 (d, J=8.0 Hz, 1H), 5.37 (br, 2H), 3.84 (m, 1H), 2.98-3.24 (m, 4H), 2.12 (s, 3H). MS m/z 266.1 (M+1)+.

Provenance & Evidence