4-Cyanophenylboronic acid → HCID 46178569, compound

Participants

Reaction Steps

Pd(PPh3)4 (60 mg, 0.052 mmol) in a 100 mL flask under Ar was treated sequentially with 2′-amino-6-bromo-1′-methyl-2-phenylspiro[chroman-4,4′-imidazol]-5′(1′H)-one (100 mg, 0.26 mmol) in toluene (15.6 mL), Na2CO3 (2 N, 7.8 mL), and 4-cyanophenylboronic acid (76.5 mg, 0.52 mmol). The mixture was refluxed under Ar for 3-5 h. The reaction mixture was concentrated in vacuo to give a residue, which was purified by preparative TLC followed by preparative HPLC to give pure 3-(2′-amino-1′-methyl-5′-oxo-2-phenyl-1′,5′-dihydrospiro[chroman-4,4′-imidazole]-6-yl)benzonitrile (31 mg, 29%) as a racemic product. 1H-NMR (CDCl3): 2.18 (m, 1H), 2.29 (t, 1H), 3.13 (s, 3H), 5.90 (d, 1H), 7.05 (d, 1H), 7.25 (m, 1H), 7.34 (m, 1H), 7.38 (m, 2H), 7.45 (m, 2H), 7.50-7.64 (m, 3H), 7.82-7.87 (m, 2H).

Provenance & Evidence