Ethyl bromoacetate → HCID 86599795, compound

HRID 1374788Notes

Reaction equation

HRID 1374788 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([CH3:18])[CH:16]=3)[NH:11][C:10]=2[CH3:19])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([CH3:18])[CH:16]=3)[N:11]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:10]=2[CH3:19])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 21077832HCID 21077832, compound

Product 1

HCID 86599795HCID 86599795, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 3-[(4-chlorophenyl)thio]-2,5-dimethyl-1H-indole (300 mg) in dry N,N-dimethylformamide (15 ml) was treated with sodium hydride (42 mg of a 60% dispersion in mineral oil). After 10 minutes the reaction was treated with ethyl bromoacetate (116 μl) and stirring continued for 24 hours. The reaction was poured into distilled water (200 ml) and extracted with diethyl ether (3×100 ml). The extracts were dried (MgSO4), evaporated in vacuo and the residue purified by flash column chromatography eluting with 10% ethyl acetate in iso-hexane. The subtitle compound was obtained as a yellow solid (yield 130 mg).

Workup

  1. additionThe reaction was poured
  2. distillationinto distilled water (200 ml)
  3. extractionextracted with diethyl ether (3×100 ml)
  4. dry with materialThe extracts were dried (MgSO4)
  5. customevaporated in vacuo
  6. customthe residue purified by flash column chromatography
  7. washeluting with 10% ethyl acetate in iso-hexane

Sources & evidence

ORD record
ord-c65a9324bca948b085578e1e8f798c08
Source dataset
uspto-grants-2007_01
Patent number
US07166607B2

Reaction notes

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