1-Chloro-3-iodobenzene → HCID 11750293, compound

Participants

Reaction Steps

To a stirred solution of 6-amino-4-(4-chlorophenyl)-1,4-dimethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one (0.09 g, 0.30 mmol) and 1-chloro-3-iodobenzene (0.2 mL, 1.62 mmol) in THF (2 mL) was added Pd2(dba)3 (0.03 g, 0.03 mmol), BINAP (0.03 g, 0.05 mmol), sodium t-butoxide (0.07 g, 0.45 mmol), and 18-crown-6 (0.12 g, 0.45 mmol). The reaction mixture was stirred at room temperature for 2 days, quenched with ammonium chloride solution (sat.) and extracted several times with ethyl acetate. The combined organic layers were dried over magnesium sulfate and concentrated. Flash silica gel column separation with 20% ethyl acetate/hexane followed by trituration with hexane gave the title compound as brown solid (0.02 g, 18%). 1H NMR (DMSO-d6): δ 8.43 (s, 1H), 7.46 (dd, J=6.7, 2.0 Hz, 2H), 7.31 (dd, J=6.8, 2.2 Hz, 2H), 7.28 (m, 2H), 7.10 (d, J=10.5 Hz, 1H), 7.09 (s, 1H), 6.94 (m, 2H), 6.80 (m, 1H), 3.17 (s, 3H), 1.92 (s, 3H); MS (ESI) m/z [M+H]+ (413/415); MS (ESI) m/z [M−H]−(411/413); Anal. calcd for C22H18Cl2N2O2: C, 63.93; H, 4.39 N, 6.78. Found: C, 62.88; H, 4.72; N, 5.67.

Provenance & Evidence