Potassium Carbonate → tert-butyl 4-(4-chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Participants

Reaction Conditions

Reaction Steps

7-Benzenesulfonyl-4-chloro-6-iodo-7H-pyrrolo[2,3-d]pyrimidine (4.05 g, 9.65 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (2.985 g, 9.65 mmol), potassium carbonate (2.935 g, 21.25 mmol) and dichlorobis(triphenylphosphine)-palladium(II) (678 mg, 0.96 mmol) were combined in dioxane/water (85 mL:21 mL) and heated to 90° C. for 2 h. After cooling the reaction mixture was extracted with ethyl acetate (3×50 mL), the organic layers were combined and washed with aqueous sodium bicarbonate, brine and finally water. The organic layer was dried over anhydrous magnesium sulphate, filtered and pre-absorbed onto silica in vacuo. Purification on silica gel by gradient elution with isohexane:ethyl acetate (6:1) finishing with isohexane:ethyl acetate (4:1) yielded a yellow solid. 1H NMR (d6-DMSO, 400 MHz) 8.8(1H, s), 8.0 (2H, d), 7.8(1H,m), 7.6(2H,m), 6.8(1H, s), 6.0(1H, s), 4.1(2H, br. s), 3.6(2H,m), 2.5(2H, br. s), and 1.5(9H, s); LC/MS: m/z 474 [M+H]+, Rt=4.42 min

Provenance & Evidence