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

Participants

Reaction Conditions

Reaction Steps

6-Bromo-5′-methylspiro[chroman-4,2′-imidazol]-4′-amine (73 mg, 0.25 mmol, Intermediate 4), 3,5-dichlorophenylboronic acid (95 mg, 0.50 mmol) and K2CO3 (83 mg, 0.60 mmol) were mixed in dioxane (2 mL) and degassed by passing nitrogen through for 5 min. Then (1,1′-bis(diphenyl-phosphino)ferrocene)-dichloropalladium(II) (10 mg, 0.01 mmol) was added and the mixture was heated in a sealed vial at 100° C. overnight. (1,1′-Bis(diphenylphosphino)ferrocene)-dichloro-palladium(II) (10 mg, 0.01 mmol) was added and heating continued in a microwave oven at 130° C. for 2×1 h. Purification by preparative HPLC gave the title compound (13 mg, 14% yield): 1H NMR (400 MHz, CDCl3) δ ppm 2.04-2.30 (m, 2 H), 2.38 (s, 3 H), 4.50-4.69 (m, 2 H), 4.88 (br s, 2 H), 6.69 (s, 1 H), 6.98 (d, 1 H), 7.22-7.35 (m, 4 H); MS (ES+) m/z 360 [M+H]+.

Provenance & Evidence