Dimethylformamide → Methyl N-methylindole-6-carboxylate

HRID 252832Notes

Reaction equation

HRID 252832 reaction equation
N1C2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([OH:12])=[O:11])[CH:8]=2)[CH:3]=C1.[H-].[Na+].[CH3:15]I.[CH3:17][N:18]([CH3:21])[CH:19]=O>>[CH3:17][N:18]1[C:21]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([O:12][CH3:15])=[O:11])[CH:8]=2)[CH:3]=[CH:19]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 5952301H-indole-6-carboxylic acid

Product 1

HCID 639843Methyl N-methylindole-6-carboxylate

Procedure

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).

Workup

  1. additionAfter complete addition
  2. customQuenching with water
  3. customfollowed by rotary evaporation
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto provide crude 166 (it

Sources & evidence

ORD record
ord-92d41947951d4d30afe6093e0cee5ace
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Reaction notes

Loading…