Sodium Carbonate → HCID 57906583, compound

Participants

Reaction Conditions

Reaction Steps

In a sealed tube, a mixture of 6-bromo-7-(tert-butoxycarbonylamino-methyl)-imidazo[1,2-a]pyridine-3-carboxylic acid ethyl ester (1.4 g, 3.52 mmol), 2,4-dichloro-benzeneboronic acid (1.01 g, 5.29 mmol), Pd(PPh3)4 (203 mg, 0.18 mmol) and Na2CO3 (2.0 M solution in water, 6.2 mL) in DME (20 mL) was heated at 150° C. for 17 min under microwave irradiation. The reaction mixture was cooled to RT, diluted in AcOEt (400 mL) and washed with a 2.0 M aqueous Na2CO3 solution (2×200 mL). The organic layer was dried over Na2SO4, filtered, and evaporated. The residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, [hexane/DCM 1:1]/TBME 95:5→2:8) to yield the title compound (1.39 g, 2.81 mmol, 80%). MS: 464 [M+1]+; HPLC: AtRet=2.31; TLC: RF 0.47 (hexane/DCM/TBME 1:1:2).

Provenance & Evidence