4-Cyanophenylboronic acid → HCID 46178569, compound

Participants

Reaction Steps

Pd(PPh3)4 (28 mg, 0.073 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 (28 mg, 0.073 mmol) in toluene (4.4 mL), Na2CO3 (2 N, 2.2 mL) and 4-cyanophenylboronic acid (12.9 mg, 0.088 mmol). The mixture was refluxed under Ar for 3-5 h. The reaction mixture was concentrated in vacuo to give the 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 (2.58 mg, 9%). 1H-NMR (CDCl3): 0.92 (m, 1H), 1.07 (m, 1H), 1.75 (s, 3H), 4.32 (d, 1H), 5.62 (d, 1H), 5.82-5.98 (m, 5H), 6.06 (m, 2H), 6.15 (m, 2H), 6.47 (d, 1H), 6.46 (s, 1H).

Provenance & Evidence