4-(Methanesulfonyl)phenylboronic acid → HCID 58424288, compound

Participants

Reaction Conditions

Reaction Steps

Pd(PPh3)2Cl2 (10 mg) in a 10 mL 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-(methylsulfonyl)phenylboronic acid (20.8 mg, 0.1 mmol). The mixture was heated in a microwave reactor at 120° C. for 30 min. The reaction mixture was concentrated in vacuo to give the residue, which was purified by preparative TLC to give pure 2′-amino-1′-methyl-6-(4-(methylsulfonyl)phenyl)-2-phenylspir-o[chroman-4,4′-imidazol]-5′(1′H)-one (18 mg, 80%). 1H-NMR (CDCl3+MeOD): 2.07 (dd, 1H), 2.41 (t, 1H), 3.01 (s, 3H), 3.12 (s, 3H), 5.25 (d, 0.5H), 5.89 (d, 1H), 6.90 (d, 1H), 7.31 (s, 2H), 7.32 (t, 2H), 7.39 (d, 3H), 7.60 (t, 2H), 7.87 (d, 2H).

Provenance & Evidence