Potassium Carbonate → HCID 57527204, compound

Participants

Reaction Steps

A solution of 5-chloro-N-isopropylthiazolo[5,4-b]pyridin-2-amine (2.06 g, 9.05 mmol, 1.0 eq.), Pd(OAc)2 (0.2084 g, 0.928 mmol, 0.1 eq.), 1,3-bis(diphenylphosphino)propane (0.3775 g, 0.915 mmol, 0.1 eq.) and K2CO3 (1.90 g, 13.7 mmol, 1.5 eq.) in MeOH (24 mL) and DMF (12 mL) was stirred under an atmosphere of CO inside a bomb (42 psi) at 92° C. overnight. After cooling to room temperature, the reaction mixture was filtered through Celite and rinsed with MeOH. The filtrate was concentrated in vacuo, diluted with EtOAc and water. The layers were separated, and the organic layer was washed with brine and 10% aqueous LiCl, dried over Na2SO4, filtered and concentrated in vacuo. Silica gel chromatography using CH2Cl2:MeOH (10:0.1) as eluent afforded methyl 2-(isopropylamino)thiazolo[5,4-b]pyridine-5-carboxylate as a white solid (1.67 g, 74% yield).

Provenance & Evidence