Methyl iodide → Ethyl 4-benzyloxy-1-methylindole-2-carboxylate

HRID 1829778Notes

Reaction equation

HRID 1829778 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH:13]=[C:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[NH:15]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:25]I>CN(C=O)C>[CH2:3]([O:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH:13]=[C:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:15]2[CH3:25])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 119707Ethyl 4-(phenylmethoxy)-1H-indole-2-carboxylate

Product 1

HCID 22054863Ethyl 4-benzyloxy-1-methylindole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of sodium hydride (0.27 g, 60% dispersion in mineral oil) in DMF (50 mL) under nitrogen at room temperature was added ethyl 4-benzyloxyindole-2-carboxylate (1.59 g). Methyl iodide (0.5 mL) was added 10 min later. After 2 h excess sodium hydride was quenched with acetic acid (0.4 mL) and the solvent evaporated under reduced pressure. The residue was taken into EtOAc, washed with water and brine, dried over MgSO4, and evaporated to dryness to give an oil which was triturated with hexane to precipitate 1.45 g of the title compound. M.P. 89–90.5° C.

Workup

  1. customAfter 2 h excess sodium hydride was quenched with acetic acid (0.4 mL)
  2. customthe solvent evaporated under reduced pressure
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness
  6. customto give an oil which
  7. customwas triturated with hexane
  8. customto precipitate 1.45 g of the title compound

Sources & evidence

ORD record
ord-5dc5e74147644d808a846e20e525cf2b
Source dataset
uspto-grants-2006_06
Patent number
US07064143B1

Reaction notes

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