Hexachloroethane → HCID 71285111, compound

Participants

Reaction Steps

To a solution of methyl 2,4-bis(benzyloxy)-6-(3-cyano-1-methyl-1H-indol-5-yl)-5-ethylnicotinate (1.80 g, 3.39 mmol), prepared in Example 359 step 2, in THF (24 mL) was added LDA solution (1.5M in cyclohexane, 3.40 mL, 5.10 mmol, 1.5 eq) dropwise at −78° C. The reaction mixture was stirred for 15 min before a solution of hexachloroethane (1.21 g, 5.1 mmol, 1.5 eq) in THF (6 mL) was added dropwise at −78° C. The reaction progress was monitored by LC-MS. Upon completion, the reaction was quenched with sat. NH4Cl solution then extracted with Et2O (4×30 mL). The combined organic layers were dried over Na2SO4 then concentrated to give a crude product which was purified by flash column chromatography (0-10% EtOAc in 1/1 CH2Cl2/hexanes) to afford the title compound (1.58 g, 82%).

Provenance & Evidence