{4-[(2-Methylpropyl)carbamoyl]phenyl}boronic acid → HCID 67385227, compound

Participants

Reaction Conditions

Reaction Steps

Pd(PPh3)2Cl2 (10 mg) in a 10 mL CEM test tube 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 4-(isobutylcarbamoyl)-phenyl-boronic acid (23 mg, 0.1 mmol). The mixture was heated at 120° C. in a microwave reactor for 30 mins. The reaction mixture was concentrated in vacuo to give the residue, which was purified by preparative TLC to give pure 4-(2′-amino-1′-methyl-5′-oxo-2-phenyl-1′,5′-dihydrospiro[chroman-4,4′-imidazole]-6-yl)-N-isobutylbenzamide (1.28 mg, 5%). 1H-NMR (MeOD): 0.96 (d, 6H), 1.94 (m, 1H), 2.15 (d, 1H), 2.47 (t, 1H), 3.29 (s, 3H), 3.31 (s, 1H), 3.32 (s, 1H), 5.30 (d, 1H), 7.06 (t, 2H), 7.33 (m, 1H), 7.42 (t, 2H), 7.48 (d, 3H), 7.53 (d, 1H), 7.66 (d, 1H), 7.72 (d, 1H), 7.91 (s, 1H).

Provenance & Evidence