Ethyl bromoacetate → HCID 86755732, compound

HRID 1953295Notes

Reaction equation

HRID 1953295 reaction equation
N1C2C(=CC=CC=2[S:11]([NH:14][C:15]2[CH:33]=[CH:32][C:18]3[C:19]([Br:31])=[C:20]([CH2:22][C:23]4[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=4)[O:21][C:17]=3[CH:16]=2)(=[O:13])=[O:12])C=CC=1.[H-].[Na+].Br[CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39].O1[CH2:47][CH2:46][CH2:45][CH2:44]1>C(OCC)(=O)C>[CH2:41]([O:40][C:38]([CH2:37][N:14]1[C:15]2[C:47](=[CH:19][CH:18]=[CH:17][C:16]=2[C:32]2[CH:33]=[C:15]([N:14]=[S:11](=[O:12])=[O:13])[C:16]3[C:19]([Br:31])=[C:20]([CH2:22][C:23]4[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=4)[O:21][C:17]=3[CH:18]=2)[CH:46]=[CH:45][CH2:44]1)=[O:39])[CH3:42]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 23302733HCID 23302733, compound

Product 1

HCID 86755732HCID 86755732, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1.0 g (2 mmol) of 4-[(6-(quinolin-8-yl-sulphonylamino)-3-bromo-benzofuran-2-yl)-methyl]-benzonitrile are dissolved in 20 ml absolute tetrahydrofuran and after the addition of 100 g (2 mmol) of sodium hydride (50% in oil) stirred for 20 minutes at ambient temperature. Then 0.22 ml (2 mmol) of ethyl bromoacetate are added under a nitrogen atmosphere. The reaction mixture is refluxed for 6 hours, cooled, diluted with ethyl acetate and washed with sodium chloride solution. The combined organic extracts are dried and concentrated by evaporation. The residue is chromatographed on silica gel and eluted with petroleum ether/ethyl acetate (90:10 and 75:25). The desired fractions are combined and concentrated by evaporation.

Workup

  1. temperatureThe reaction mixture is refluxed for 6 hours
  2. temperaturecooled
  3. washwashed with sodium chloride solution
  4. customThe combined organic extracts are dried
  5. concentrationconcentrated by evaporation
  6. customThe residue is chromatographed on silica gel
  7. washeluted with petroleum ether/ethyl acetate (90:10 and 75:25)
  8. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-125db66e8918491894a8cf739cd878e8
Source dataset
uspto-grants-2000_09
Patent number
US06114532

Reaction notes

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