3-Cyanomethylphenylboronic acid → HCID 46178724, Verbindung

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

Pd(PPh3)2Cl2 (10 mg, 0.014 mmol) in a 10 mL tube under Ar was treated sequentially with 2′-amino-6-bromo-1′-(cyclohexylmethyl)-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-(cyanomethyl)phenylboronic acid (16.7 mg, 0.104 mmol). The mixture was heated at 120° C. in a microwave reactor for 0.5 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 2-(3-(2′-amino-1′-methyl-5′-oxo-2-phenyl-1′,5′-dihydrospiro[chroman-4,4′-imidazole]-6-yl)phenyl)acetonitrile (5.25 mg, 24%). 1H-NMR (MeOD): 2.04 (m, 1H), 2.21 (m, 1H), 3.08 (d, 3H), 3.85 (s, 2H), 5.21 (d, 0.2H), 5.81 (d, 0.8H), 6.94 (d, 1H), 7.11 (m, 1H), 7.24 (m, 2H), 7.35 (m, 3H), 7.39 (m, 5H).

Herkunft & Nachweise