Methylamine → Ethyl 4-[(4-methoxyphenyl)amino]-6-(methylcarbamoyl)quinoline-3-carboxylate

Participants

Reaction Steps

Ethyl 6-bromo-4-[(4-methoxyphenyl)amino]quinoline-3-carboxylate (0.25 g, 0.623 mmol) was added to THF followed by Herrmann's palladacycle (trans-di(μ-acetato)-bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II), 0.031 mmol), [(t-Bu)3PH]BF4 (tri tertiarybutyl phosphonium tetrafluoroborate, 0.125 mmol), Mo(CO)6 (molybdenum hexacarbonyl, 1.246 mmol), methylamine (1.5 equiv., 2N in THF) and DBU (1,8-diazabicyclo[5.4.0]undec-7-ene, 1.869 mmol). The reaction mixture was irradiated at 130° C. for 5 minutes in a microwave reactor. The reaction mixture was concentrated and then purified on column (silica gel, dichloromethane/methanol 98:2) to give 0.25 g (71%) of ethyl 4-[(4-methoxyphenyl)amino]-6-(methylcarbamoyl)quinoline-3-carboxylate. 1H NMR (300 MHz, CDCl3) δ 10.96 (s, 1H, —NH—) 9.24 (s, 1H, aromatic), 8.14-7.98 (m, 2H, aromatic), 7.73 (s, 1H, aromatic), 7.16 (d, 2H, J=9 Hz, aromatic), 6.98 (d, 2H, J=9 Hz, aromatic), 4.46 (q, 2H, J=7 Hz, —CH2—), 3.87 (s, 3H, —OCH3), 1.48 (t, 3H, J=7Hz, —CH3); LC-MS (m/z) 380.0 (M+1).

Provenance & Evidence