Azetidine → HCID 44177925, compound

Participants

Reaction Conditions

Reaction Steps

4-bromo-1-(3′-(methylsulfonyl)biphenyl-4-yl)-2-(2-(trifluoromethyl)phenyl)-1H-imidazole (188 mgs, 0.361 mmol), azetidine (0.4 mL 5.94 mmol), L-proline (50 mg, 0.434 mmol), Cs2CO3 (517 mg, 1.44 mmol), 2.5 mL anhydrous DMF, and CuI (69 mg, 362 mmol) were added to a 5 mL microwave tube and sealed. The tube was purged with an argon balloon for five minutes. The reaction was heated at 120° C. for 24 h and then cooled to room temperature. The crude reaction mixture was purified directly by HPLC using water: TFA: acetonitrile as eluents to afford 4-(azetidin-1-yl)-1-(3′-(methylsulfonyl)biphenyl-4-yl)-2-(2-(trifluoromethyl)phenyl)-1H-imidazole (47 mgs, 26%) as a light yellow solid. 1H-NMR (DMSO, 400 MHz) δ 8.12-8.11 (m, 1H), 8.02-7.99 (m, 1H), 7.91-7.88 (m, 1H), 7.82-7.80 (m, 1H), 7.76 (d, J=8.60 Hz, 2H), 7.73-7.69 (m, 1H), 7.65-7.62 (m, 2H), 7.46-7.44 (m, 1H), 7.23 (d, J=8.60 Hz, 2H), 6.77 (s, 1H), 3.74 (t, J=7.34 Hz, 4H), 3.28 (s, 3H), 2.33-2.25 (m, 2H); MS (ES): 498.3 [M+H]+.

Provenance & Evidence