Methyl iodide → Methyl 1-methyl-1H-indole-3-carboxylate

HRID 1921004Notes

Reaction equation

HRID 1921004 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([O:14][CH3:15])=[O:13])=[CH:4]1.[CH3:16]I>CN(C=O)C.O>[CH3:16][N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([O:14][CH3:15])=[O:13])=[CH:4]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydride2×HCID 589098Methyl indole-3-carboxylate

Product 1

HCID 842006Methyl 1-methyl-1H-indole-3-carboxylateYield 96.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

NaH (60% dispersion in mineral oil, 8.56 g, 214.0 mmole) was added portion wise, allowing for gas evolution, to a solution of methyl 1H-indole-3-carboxylate (25.00 g, 142.7 mmole) in DMF (350 mL) at 0° C. When the NaH addition was complete, methyl iodide (44.4 mL, 713.5 mmole) was added at 0° C. The reaction was stirred at 0° C. for 15 minutes then at RT overnight. The reaction was diluted with water and extracted with ethyl acetate. The combined extracts were dried over K2CO3 and concentrated to afford the title compound (26.00 g, 96%) as an orange solid: MS (ES) m/e 190 (M+H)+.

Workup

  1. customat RT
  2. customovernight
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined extracts were dried over K2CO3
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e84195de2f544c3f9a497e1b05267e9b
Source dataset
uspto-grants-2012_05
Patent number
US08173646B2

Reaction notes

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