Dichloromethane → 4-[5-(1-methyl-1H-[1,2,4]triazol-3-yl)-thiophen-2-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

To a large pressure flask were charged compound 3-(5-bromo-thiophen-2-yl)-1-methyl-1H-[1,2,4]triazole (3.1 g, 12.8 mmols) (5BW), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (3.6 g, 11.65 mmols), [1,1′-bis(diphenylphosphino)-ferrocene]dichloro-palladium (II), complex with dichloromethane (1:1) (0.475 g, 0.89 mmols), Na2CO3 (8.5 ml) and dioxane (40 ml). The mixture was briefly degassed with Ar for ˜0.5 minute, capped and stirred at 80° C. overnight. After cooling, the reaction mixture was diluted with EtOAc and brine. Organic layer was isolated, and dried MgSO4. After concentration, the residue was purified on silica gel. Elution with EtOAc (100%) gave the desired product (6BW) (3.5 g).

Provenance & Evidence