反应详情

To a mixture of 5-(1-methylindol-2-yl)-1,3-thiazole-2-ylamine (53, 10 mg, 0.043 mmol) in 1 ml DCM were added 2-chlorobenzoyl chloride (11 μl, 2 eq), DIEA (37 μl, 3 eq) and DMAP (2 mg). After stirred at r.t for overnight, the reaction mixture was worked up with DCM/aq. NaCO3, the DCM phase was concentrated to dryness. The solid residue was dissolved in 2 ml THF/MeOH/H2O (5:4:1). 0.1 ml of 1N NaOH were added and mixture was stirred at r.t for 1 h before worked up DCM//aq. NaCO3. DCM phase was concentrated and subjected to silica gel flash column to give 15.3 mg of (2-chlorophenyl)-N-[5-(1-methylindol-2-yl)(1,3-thiazol-2-yl)]carboxamide (54) as yellow solid (yield: 97%; purity>95%). LC-MS: calcd. for C18H14ClN3OS: 368 (M+1).

1. concentrationNaCO3, the DCM phase was concentrated to dryness
2. dissolutionThe solid residue was dissolved in 2 ml THF/MeOH/H2O (5:4:1)
3. addition0.1 ml of 1N NaOH were added
4. stirringmixture was stirred at r.t for 1 h
5. concentrationDCM phase was concentrated