Benzyl Chloride → Ethyl 1-benzyl-5-chloro-1H-indole-2-carboxylate

Temperature

100 °C

5-Chloroindole-2-carboxylic acid ethyl ester (1.4 g) was dissolved in N,N-dimethylformamide (30 mL), and to the solution were added potassium carbonate (2.9 g) and benzyl chloride (2.4 mL), followed by stirring in a bath at a temperature of 100° C. for 1.5 hours. The reaction mixture was concentrated, and the residue was poured into ice water. The thus-obtained mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and was dried over sodium sulfate anhydrate. The solvent was distilled away, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:19). The thus-obtained compound was crystallized from diethyl ether-hexane, to thereby give the title compound (1.6 g).

1. concentrationThe reaction mixture was concentrated
2. additionthe residue was poured into ice water
3. extractionThe thus-obtained mixture was extracted with ethyl acetate
4. washThe organic layer was washed with saturated brine
5. dry with materialwas dried over sodium sulfate anhydrate
6. distillationThe solvent was distilled away
7. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:19)
8. customThe thus-obtained compound was crystallized from diethyl ether-hexane

ORD record

ord-df33cd28ef834a67829048bf6b48c6f6

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07576135B2