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0 °C

NaH (96 mg, 4 mmol) was suspended in 7 mL DMF in a round bottom flask and cooled to 0° C. 6-bromo-4-methoxy-1H-indole (0.75 g, 3.3 mmol) was added dropwise as a solution in DMF (1 mL). Ethyl iodide (0.28 mL, 3.5 mmol) was added dropwise and the reaction mixture was stirred for 10 min. Volatiles were removed under reduced pressure and the residue partitioned between DCM and water. The aqueous layer was extracted with DCM and the combined organics layers were dried over MgSO4, filtered, and evaporated to give a red oil. The resulting residue was purified on silica gel column chromatography eluting with hexanes/ethyl acetate (0-10%) to afford pure 36-2 (584 mg, 70%) as a white solid.

1. customVolatiles were removed under reduced pressure
2. customthe residue partitioned between DCM and water
3. extractionThe aqueous layer was extracted with DCM
4. dry with materialthe combined organics layers were dried over MgSO4
5. filtrationfiltered
6. customevaporated
7. customto give a red oil
8. customThe resulting residue was purified on silica gel column chromatography
9. washeluting with hexanes/ethyl acetate (0-10%)