Nitrogen → HCID 67286052, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl-[4-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-3-ylmethyl]-carbamic acid tert-butyl ester (1.5 g, 5.1 mmol) and 2-bromo-isonicotinic acid methyl ester (1.3 g, 6.1 mmol) were suspended in 1,4-dioxane (25 mL). To the mixture was added K3PO4.3H2O (0.90 g, 4.52 mmol, 1 M in water). The reaction was degassed with N2 and PdCl2(PPh3)2 (72 mg, 0.1 mmol) was added. The reaction was heated to 60° C. for 3 hours. The mixture was then diluted with water and neutralised to pH 7. The mixture was concentrated in vacuo, to remove organic solvent, and then partitioned between water and EtOAc. The aqueous layer was extracted with EtOAc (×3). The combined organic layers were washed with water, brine, dried (MgSO4) and then evaporated to dryness. Purification by SiO2 chromatography gave the title compound (1.36 g). m/z 386 (M+H)+

Provenance & Evidence