N-Methoxy-N-methylbutyramide → HCID 71285237, compound

Participants

Reaction Conditions

Reaction Steps

To solution of 5-bromo-2-(2-(tert-butyldimethylsilyloxy)ethyl)-1-methyl-1H-indole (9.963 g, 27.04 mmol) in THF (100 mL) at −78° C. was added solution of n-BuLi (2.5M hexanes, 13.0 mL, 32.50 mmol) dropwise over 10 min. Reaction was stirred at −78° C. for 10 min before solution of N-methoxy-N-methylbutyramide (4.30 g, 32.78 mmol) in THF (10 mL) was added dropwise. Reaction was stirred at −78° C. for 15 min and then quenched with NH4Cl (aqueous saturated, 30 mL). Once ambient temperature was reached in the reaction mixture product was extracted with EtOAc (2×100 mL). Combined organics were washed with NaCl (aqueous saturated) and dried over Na2SO4. Upon solvent removal residue was purified by column chromatography using EtOAc/hexanes (gradient 0-30%) to afford 1-(2-(2-(tert-butyldimethylsilyloxy)ethyl)-1-methyl-1H-indol-5-yl)butan-1-one (6.620 g, 68%) as white solid.

Provenance & Evidence