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

HRID 749294Notes

Reaction equation

HRID 749294 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 gm). Methyl iodide (0.5 mL) was added 10 min. later. After 2 hr. 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. Mp 89-90.5° C.

Workup

  1. customexcess 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-1aa8a9db03b541abab1cb95525cf4d22
Source dataset
uspto-grants-2008_07
Patent number
US07402604B2

Reaction notes

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