Ethyl bromoacetate → HCID 10229780, compound

HRID 585413Notes

Reaction equation

HRID 585413 reaction equation
[CH2:1]([O:8][C:9](=[O:34])[CH2:10][O:11][C:12]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH:18]=[C:17]2[C:13]=1[CH:14]=[C:15]([CH2:32][CH3:33])[N:16]2[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:42]1C2CC3C=CC=CC=3C(=O)C=2C=C1CC)C1C=CC=CC=1.[C:58](=[O:61])([O-])[O-].[Cs+].[Cs+].BrCC([O:68][CH2:69]C)=O>CN(C)C=O.O>[CH2:1]([O:8][C:9](=[O:34])[CH2:10][O:11][C:12]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH:18]=[C:17]2[C:13]=1[C:14]([C:58](=[O:61])[C:69]([NH2:42])=[O:68])=[C:15]([CH2:32][CH3:33])[N:16]2[CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 20823166HCID 20823166, compoundHCID 22340091HCID 22340091, compound

Product 1

HCID 10229780HCID 10229780, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Preparation of (1-benzyl-2-ethyl-1H-benzo[f]indol-4-yloxy)acetic acid benzyl ester. A mixture of 1-benzyl-2-ethyl-1,9-dihydrobenzo[f]indol-4-one (200 mg, 0.67 mmol), cesium carbonate (436 mg, 1.39 mmol), and ethyl bromoacetate (0.21 mL, 1.34 mmol) in N,N-dimethylformamide (5 mL) was stirred at room temperature for 20 h. The mixture was diluted with water and the resulting solution extracted three times with ethyl acetate. The combined ethyl acetate extracts were washed three times with water, filtered through a plug of silica gel, and concentrated in vacuo. Chromatography (hexane/methylene chloride) of the residue provided 120 mg (40%) of the title compound as a yellow film.

Workup

  1. extractionthe resulting solution extracted three times with ethyl acetate
  2. washThe combined ethyl acetate extracts were washed three times with water
  3. filtrationfiltered through a plug of silica gel
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c39771bdfae4468884459a86aae61ae2
Source dataset
uspto-grants-2005_08
Patent number
US06930123B2

Reaction notes

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