Potassium Carbonate → 6-(3,5-Difluorophenyl)-5'-methylspiro[chroman-4,2'-imidazol]-4'-amine

Participants

Reaction Conditions

Reaction Steps

6-Bromo-5′-methylspiro[chroman-4,2′-imidazol]-4′-amine (Intermediate 4, 0.10 g, 0.34 mmol), 3,5-difluorophenylboronic acid (0.11 g, 0.68 mmol) and 2M K2CO3 (aq., 0.34 mL, 0.69 mmol) were mixed in dioxane (3 mL) and degassed by passing through nitrogen for 5 min. Then (1,1′-bis(diphenylphosphino)ferrocene)-dichloropalladium(II) (14 mg, 20 μmol) was added and the mixture was heated in a microwave oven at 130° C. for 1 h. Purification by preparative chromatography gave the title compound (17 mg, 15% yield): 1H NMR (400 MHz, CDCl3) δ ppm 2.25 (m, 2 H), 2.41 (s, 3 H), 4.57 (m, 2 H), 6.66-6.86 (m, 2 H), 6.89-7.05 (m, 3 H), 7.38 (d, 1 H), 8.1-9.0 (br m, 2 H); MS (ES+) m/z 328 [M+H]+.

Provenance & Evidence