Reaktion #340014

Reaktionsgleichung

1H-Indole-6-carboxylic acid

dimethylformamide

sodium hydride

methyl iodide

→

Methyl 1-methyl-1H-indole-6-carboxylate

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter complete addition
2. 2
   SonstigeQuenching with water
3. 3
   Sonstigefollowed by rotary evaporation
4. 4
   Extraktionextracted with ethyl acetate
5. 5
   TrocknenThe organic phase was dried over magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Sonstigeevaporated
8. 8
   Sonstigeto provide crude 166 (it

Vorschrift

1H-Indole-6-carboxylic acid 37 (0.20 g, 1.24 mmol) was dissolved in dimethylformamide (10 mL) and cooled to 0° C. for the portion-wise addition of sodium hydride (0.20 g, 4.96 mmol). After complete addition, the reaction mixture was allowed to warm to rt and stirred for 1 hr then methyl iodide (0.15 mL, 2.48 mmol) was added to the reaction mixture. Quenching with water followed by rotary evaporation led to the crude residue, which was taken up with water and extracted with ethyl acetate. The organic phase was dried over magnesium sulfate, filtered and evaporated to provide crude 166 (it was used crude in the next step). MS: 189.08 (calc), 190.1 (obs).

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