4-Toluenesulfonyl chloride → [4-Methoxy-2-(2-propen-1-yloxy)phenyl][2-methyl-1-[(4-methylphenyl)sulfonyl]-6-(trifluoromethoxy)-1H-indol-3-yl]methanone

Participants

Reaction Steps

To a solution of 6 (8.0 g, 20 mmol) in DMF (200 mL) was added NaH (1.5 eq). Mixture stirred for 15 min before addition of TsCl (1.5 eq, 5.6 g). After 1 hour, the reaction mixture was poured into ice water and extracted with CH2Cl2. The organic layer was washed with NH4Cl (2×), NaHCO3 and brine, then dried with Na2SO4 and concentrated. Purification via flash chromatography eluding with 20% EtOAc/hexanes afforded the product as a viscous yellow oil.

Provenance & Evidence