3-Cyano-4-fluorophenylboronic acid → HCID 46178645, 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-cyano-4-fluorophenylboronic acid (17 mg, 0.104 mmol). The mixture was heated under Ar at 120° C. under microwave for 30 min. The reaction mixture was concentrated in vacuo to give the residue, which was purified by preparative HPLC twice to give pure 5-(2′-amino-1′-methyl-5′-oxo-2-phenyl-1′,5′-dihydrospiro[chroman-4,4′-imidazole]-6-yl)-2-fluorobenzonitrile (7 mg, 32%). 1H-NMR (MeOD): 2.15 (m, 1H), 2.29 (t, 1H), 3.12 & 3.18 (s, 3H), 5.30 & 5.89 (m, 1H), 7.03 (m, 1H), 7.21 (m, 1H), 7.31-7.50 (m, 6H), 7.85 (m, 2H).

Provenance & Evidence