Nitrogen → HCID 66977155, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(5-bromopyrimidin-2-yl)-4-ethyl-piperidine-4-carboxylate (0.882 g, 2.58 mmol), bis(pinacolato)diboron, (0.818 g, 2.58 mmol), potassium acetate (0.379 g, 3.87 mmol) and tricyclohexylphosphine, 43 mg, 0.15 mmol in dioxane (10 mL) was degassed with N2 for 10 mins. Pd2(dba)3 (71 mg, 0.077 mmol) was introduced and the reaction heated to 95° C. for 2 hours. TLC indicated complete consumption of tarting material. The solution was filtered through celite, the solids washed with 10 mL of dioxane and the combined filtrate added to a separate flask containing N-(7-bromo-5-pyrazol-1-yl-imidazo[1,2-a]pyridin-2-yl)carbamate (0.650 g, 1.72 mmol) and K3PO4 (0.694 g; 3.27 mmol) in dioxane (10 mL) and water (2 mL). The mixture was degassed with N2 for 10 mins then PdCl2(PPh3)2 (92 mg, 0.131 mmol) was added. The mixture was heated under N2 to 85° C. for 3 hours then cooled and diluted with EtOAc (50 mL). The suspension was filtered, yielding a slightly greenish white solid with the requisite molecular ion (MS: 561.05 [M+H]+). The crude was suspended in EtOAc (30 mL) to which was added DCM (20 mL) and MeOH (10 mL), heated until partial dissolution then cooled overnight. The solid was once again filtered, washed with a small amount of EtOAc, then heptane, and dried, giving 0.530 g (55%) of product, which was used directly in the next step without further purification.

Provenance & Evidence