3-(Dimethylcarbamoyl)benzeneboronic acid → HCID 58423963, compound

Participants

Reaction Conditions

Reaction Steps

Pd(PPh3)2Cl2 (10 mg, 0.01 mmol) in a 10 mL flask under Ar was treated sequentially with 2′-amino-6-bromo-1′-methyl-2-phenylspiro[chroman-4,4′-imidazol]-5′(1′H)-one (20 mg, 0.052 mmol) in 1,4-dioxane (1 mL), Cs2CO3 (2 N, 0.3 mL) and 3-(dimethylcarbamoyl)phenylboronic acid (20 mg, 0.104 mmol). The mixture was heated at 120° C. under Ar in a microwave reactor for 30 minutes. The reaction mixture was concentrated in vacuo to give the residue, which was purified by preparative TLC to give 3-(2′-amino-1′-methyl-5′-oxo-2-phenyl-1′,5′-dihydrospiro[chroman-4,4′-imidazole]-6-yl)-N,N-dimethylbenzamide (1.44 mg, 6%). 1H-NMR (MeOD): 2.44 (m, 1H), 2.62 (m, 1H), 3.14 (s, 3H), 3.13 (s, 1H), 5.24 (m, 0.3H), 5.88 (m, 0.7H), 7.15 (m, 1H), 7.41 (m, 3H), 7.45 (m, 1H), 7.53 (m, 4H), 7.18 (m, 3H).

Provenance & Evidence