3-Amino-5-cyanobenzeneboronic acid hydrochloride → 3-Amino-5-(2'-amino-1'-methyl-5'-oxo-2-phenyl-1',5'-dihydrospiro [chroman-4,4'-imidazole]-6-yl)benzonitrile

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

Pd(PPh3)2Cl2 (10 mg) 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-amino-5-cyanophenylboronic acid hydrochloride (21 mg, 0.104 mmol). The mixture was heated at 120° C. under 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 3-amino-5-(2′-amino-1′-methyl-5′-oxo-2-phenyl-1′,5′-dihydrospiro [chroman-4,4′-imidazole]-6-yl)benzonitrile (3.53 mg, 16%). 1H-NMR (MeOD): 2.44 (m, 1H), 2.60 (m, 1H), 5.24 (d, 0.3H), 5.85 (d, 0.7H), 6.91 (m, 1H), 7.14 (m, 3H), 7.48 (m, 6H), 7.60 (m, 1H).

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