N-Methoxy-N-methylpropionamide → 1-(2-((tert-Butyldimethylsilyloxy)methyl)-1-methyl-1H-indol-5-yl)propan-1-one

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 5-bromo-2-((tert-butyldimethylsilyloxy)methyl)-1-methyl-1H-indole (3.76 g, 10.6 mmol), prepared according to procedure described in Example 39 Step 3, in THF (15 mL) was added n-BuLi (2.5 M solution in hexanes, 5.1 mL, 12.7 mmol, 1.2 eq) at −78° C. dropwise. The mixture was stirred for 30 min at −78° C. before a solution of N-methoxy-N-methylpropionamide (1.49 g, 12.7 mmol, 1.2 eq) in THF (5 mL) was added. After stirred at −78° C. for 10 min, the reaction was quenched with saturated aqueous NH4Cl solution. The resulting mixture was extracted by ether (3×30 mL) and combined organic layers were dried over Na2SO4. The crude product was purified by flash chromatography (0-10% EtOAc in hexanes) to give the title compound (2.70 g, 77%).

Provenance & Evidence