Potassium Carbonate → Tert-butyl 4-(2-tert-butoxypyridin-4-yl)benzylcarbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-((tert-butoxycarbonylamino)methyl)phenylboronic acid (1 g, 3.98 mmol), potassium carbonate (1.1 g, 7.96 mmol), 4-Bromo-2-(t-butoxy)pyridine (1.1 g, 4.78 mmol) in degassed toluene/EtOH/water (2:1:1) (6 mL) was added [1,1′-Bis (diphenylphosphino)ferrocene]dichloropalladium (II) (0.14 g, 0.199 mmol). The reaction mixture was then heated in the microwave at 75° C. for 30 min. After cooling the mixture, it was purified by silica gel chromatography (eluent: CH2Cl2/ethyl acetate 95:5) to yield tert-butyl 4-(2-tert-butoxypyridin-4-yl)benzylcarbamate (1). MS found for C21H28N2O3 as (M+H)+ 356.8. To the above Boc protected compound (462 mg, 1.3 mmol) in CH2Cl2 (3 mL), 4.0 M HCl dioxane (1.6 mL, 6.5 mmol) was added and stirred at rt for 1 h. The reaction mixture was then diluted with ether and the resulting solids were filtered and washed with ether and dried to give 4-(4-(aminomethyl)phenyl)pyridin-2(1H)-one (2) as hydrochloride salt. C12H12N2O 201.0 (M+1).

Provenance & Evidence