Iodoethane → HCID 66772785, compound

HRID 1645332Notes

Reaction equation

HRID 1645332 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[C:12]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:11]=[CH:10][CH:9]=2)=[O:5])[CH3:2].[H-].[Na+].[CH2:25](I)[CH3:26]>CN(C=O)C.CCOC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:25][CH3:26])[C:8]2[C:13]([CH:14]=1)=[C:12]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:11]=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 119707Ethyl 4-(phenylmethoxy)-1H-indole-2-carboxylate

Product 1

HCID 66772785HCID 66772785, compoundYield 104.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-benzyloxy-1H-indole-2-carboxylic acid ethyl ester (1.0 g, 3.40 mmol) in DMF (2 mL) was added drop wise to a suspension of NaH (100 mg, 4.0 mmol) in DMF (5 mL). The reaction mixture was stirred for 30 min. Ethyl iodide (624 mg, 4.0 mmol) diluted in 1 mL of DMF was added drop wise at room temperature and the mixture was stirred for an additional 1 hr. The reaction mixture was diluted with 100 mL of EtOAc and washed with 100 mL of saturated ammonium chloride, brine (50 mL), dried over anhydrous sodium sulfate and the solvent was removed to afford crude 4-benzyloxy-1-ethyl-1H-indole-2-carboxylic acid ethyl ester (1.15 g). This material was diluted in 30 mL of ethanol and 100 mg of 10% Pd/C was added. The mixture was placed on a Parr shaker for hydrogenation at 50 psi for 3 hr. The mixture was filtered and the solvent was removed to afford 1-ethyl-4-hydroxy-1H-indole-2-carboxylic acid ethyl ester (0.730 g, 92% yield) as a white solid. LCMS for C13H15NO3 calcd. (m/e) 233, observed 234 (M+H).

Workup

  1. additionwas added drop
  2. additionwas added drop wise at room temperature
  3. stirringthe mixture was stirred for an additional 1 hr
  4. washwashed with 100 mL of saturated ammonium chloride, brine (50 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-2ecc34e09ff64e2a9284958cdd83904b
Source dataset
uspto-grants-2012_02
Patent number
US08124766B2

Reaction notes

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