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

Participants

Reaction Conditions

Reaction Steps

6-Bromo-5′-methylspiro[chroman-4,2′-imidazol]-4′-amine (60 mg, 0.20 mmol, Intermediate 4), 5-chloropyridin-3-ylboronic acid (62 mg, 0.40 mmol) and 2 M K2CO3 (aq, 0.20 mL, 0.41 mmol) were mixed in dioxane (5 mL) and degassed by passing nitrogen through for 5 min. Then (1,1′-bis(diphenylphosphino)ferrocene)-dichloropalladium(II) (8 mg, 10 μmol) was added and the mixture was heated in a microwave oven at 130° C. for 1 h. Purification by preparative chromatography HPLC gave the title compound (42 mg, 63% yield): 1H NMR (400 MHz, CDCl3) δ ppm 2.17 (m, 2H), 2.37 (s, 3H), 4.59 (m, 2H), 5.04 (br s, 2H), 6.73 (d, 1H), 7.01 (d, 1H), 7.34 (dd, 1H), 7.70 (m, 1H), 8.45 (m, 1H), 8.55 (m, 1H); MS (ES+) m/z 327 [M+H]+.

Provenance & Evidence