Hydrochloric Acid → Methyl 3-(3-(tert-butylthio)-1-(4-chlorobenzyl)-5-(quinolin-2-ylmethoxy)-1H-indol-2-yl)-2,2-dimethylpropanoate

Participants

Reaction Steps

Methyl 3-[N-(p-chlorobenzyl)-5-hydroxy-3-(t-butylthio)indol-2-yl]-2,2-dimethylpropanoate (33.6 g) from Step C was dissolved in 500 mL of dry DMF and the solution was charged with 2.4 g of KI, 30.3 g of K2CO3, 4.77 g of Cs2CO3 and 23.5 g of 2-(chloromethyl)quinoline hydrochloride. The reaction was stirred at RT, under N2, for 72 hours then it was poured into water (1.5 L), acidified with 1N HCl and extracted (3×200 mL) with CH2Cl2. The organic phase was washed with H2O (3×150 mL), dried and evaporated. The residue was dissolved in hot EtOAc and upon cooling crystallized to deposit 22.0 g of the title compound, m.p. 166°-167° C.

Provenance & Evidence