Dimethylformamide → HCID 72192144, compound

Participants

Reaction Steps

To a solution of 7-chloro-4-iodo-5-methyl-1-tosyl-1H-indole (98 mg, 0.220 mmol) and DMF (34 μL, 0.440 mmol) in cyclopentyl methyl ether (2 mL) at −78° C., was added n-butyllithium (2.5 M in hexanes, 114 μL, 0.286 mmol). After 80 minutes additional n-butyllithium (2.5 M in hexanes, 0.11 mL, 0.286 mmol) was added. After 15 more minutes the reaction was quenched with MeOH (0.5 mL) and sat. aq. NH4Cl. The layers were separated and the aqueous layer was extracted with EtOAc, washed with brine, dried over MgSO4, filtered and concentrated. The resulting residue was purified by flash chromatography (0-50% EtOAc in heptanes) to provide the title compound. MS (ESI+) m/z 347.9 (M+H).

Provenance & Evidence