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0 °C

A solution of the known 6-methyl-1H-indole-3-carboxaldehyde (5 g, 31 mm) in DMF (100 mL) was cooled to 0° C. and treated with NaH (38 mm), and stirred at 0° C. for 3 hours. After treatment with CH3I (2.35 mL, 38 mm), the mixture was allowed to warm to room temperature overnight. The mixture was poured into H2O(500 mL) and extracted with ethylacetate (EtOAc) (200 mL×3). The combined organic layers were dried over MgSO4, filtered and evaporated. Purification by flash column chromatography afforded 1,6-dimethyl-1H-indole-3-carboxaldehyde (5.2 g, 97%).

1. temperatureto warm to room temperature overnight
2. extractionextracted with ethylacetate (EtOAc) (200 mL×3)
3. dry with materialThe combined organic layers were dried over MgSO4
4. filtrationfiltered
5. customevaporated
6. customPurification by flash column chromatography