Sodium Carbonate → HCID 86712632, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl 4-(4-aminophenyl)piperazine-1-carboxylate (K3) (0.845 g, 3.06 mmol), methyl 2-(2-((2-chloro-5-methylpyrimidin-4-ylethynyl)phenyl)acetate (K7) (0.460 g, 1.53 mmol), Pd2(dba)3 (0.070 g, 0.076 mmol), Xantphos (0.089 g, 0.15 mmol), and Na2CO3 (0.648 g, 6.12 mmol) in DME (16 mL) was degassed with nitrogen before heating under microwave irradiation for 30 minutes at 110° C., then a further 60 minutes at 110° C. An additional 0.1 equivalent of Pd2(dba)3 and 0.1 equivalent of Xantphos were added before the solution was degassed with nitrogen for 5 minutes and heated under microwave irradiation for 60 minutes at 110° C. The resulting mixture was filtered and the filtrate evaporated in vacuo to give a dark brown residue which was adsorbed onto silica gel and purified by column chromatography (Biotage Isolera, 40 g SiO2 cartridge, 0-100% MeOH in EtOAc), to yield the title compound A7 as brown oil (66 mg, 8%); 1H NMR (400 MHz, CDCl3) δ 8.27 (s, 1H), 7.66 (d, J=7.6 Hz, 1H), 7.53-7.46 (m, 2H), 7.44-7.28 (m, 4H), 6.94 (dd, J=7.2, 5.1 Hz, 2H), 3.96 (s, 2H), 3.70 (s, 3H), 3.58 (dd, J=11.4, 6.2 Hz, 4H), 3.11-3.04 (m, 4H), 2.33 (s, 3H), 1.49 (s, 9H). LC-MS-A: rt 6.409 min; m/z 542 [M+H]+.

Provenance & Evidence