3-Cyanophenylboronic acid → HCID 67384974, compound

Participants

Reaction Steps

Pd(PPh3)2Cl2 (10 mg) in a 10 mL of tube under Ar2 was treated sequentially with 2′-amino-6-bromo-2-phenyl-1′-(2,2,2-trifluoroethyl)spiro[chroman-4,4′-imidazol]-5′(1′H)-one (20 mg, 0.044 mmol) in 1,4-dioxane (1 mL), Cs2CO3 (2 M, 0.3 mL) and 3-cyanophenylboronic acid (13 mg, 0.088 mmol). The mixture was heated at 120 under microwave reactor for 0.5 h. The reaction mixture was concentrated in vacuo to give the residue, which was purified by preparative TLC to give pure 3-(2′-amino-5′-oxo-2-phenyl-1′-(2,2,2-trifluoroethyl)-1′,5′-dihydrospiro[chroman-4,4′-imidazole]-6-yl)benzonitrile (3.7 mg, 12%). 1H-NMR (MeOD): 2.27 (m, 1H), 2.35 (m, 1H), 3.87 (m, 2H), 5.83 (m, 1H), 7.01 (d, 1H), 7.26 (m, 1H), 7.32 (m, 5H), 7.59 (m, 3H), 7.76 (m, 1H), 7.81 (m, 1H).

Provenance & Evidence