Iodoethane → Methyl 1-ethylindole-3-carboxylate

HRID 489613Notes

Reaction equation

HRID 489613 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)=[O:4].I[CH2:15][CH3:16].[H-].[Na+]>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH2:15][CH3:16])[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 589098Methyl indole-3-carboxylate

Product 1

HCID 5191495Methyl 1-ethylindole-3-carboxylateYield 77.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A flask was charged with 1H-indole-3-carboxylic acid methyl ester (2 g, 11.41 mmol) and iodoethane (4.4 g, 28.5 mmol) in dry THF (25 mL). The mixture was stirred in a water bath and a 60% dispersion of sodium hydride (0.68 g, 17.12 mmol) in mineral oil was added in portions over 5 minutes. The reaction stirred for 48 hours and was quenched by careful addition of water. The mixture was extracted with dichloromethane (2×100 mL), dried over sodium sulfate and evaporated under reduced pressure. The crude product was purified by silica flash chromatography (10% ethyl acetate/heptane) to give 1-ethyl-1H-indole-3-carboxylic acid methyl ester (1.8 g). 1H NMR [CDCl3]: δ 8.22-8.15 (m, 1H), 7.87 (s, 1H), 7.42-7.33 (m, 1H), 7.31-7.25 (m, 2H), 4.22 (q, 2H), 3.92 (s, 3H), 1.52 (t, 3H).

Workup

  1. stirringThe reaction stirred for 48 hours
  2. customwas quenched by careful addition of water
  3. extractionThe mixture was extracted with dichloromethane (2×100 mL)
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe crude product was purified by silica flash chromatography (10% ethyl acetate/heptane)

Sources & evidence

ORD record
ord-6c107f156f9d4913ad749237b8a152b2
Source dataset
uspto-grants-2005_12
Patent number
US06977263B2

Reaction notes

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