Ethyl bromoacetate → HCID 123817435, compound

HRID 1374791Notes

Reaction equation

HRID 1374791 reaction equation
[H-].[Na+].Cl[C:4]1[CH:9]=[CH:8][C:7]([S:10][C:11]2[C:19]3[C:14](=[CH:15][C:16]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:17][CH:18]=3)[NH:13][C:12]=2[CH3:24])=[CH:6][CH:5]=1.Br[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28].O1CCC[CH2:33]1>>[CH3:24][C:12]1[N:13]([CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:14]2[C:19]([C:11]=1[S:10][C:7]1[CH:8]=[CH:9][C:4]([CH3:33])=[CH:5][CH:6]=1)=[CH:18][CH:17]=[C:16]([S:20]([CH3:23])(=[O:22])=[O:21])[CH:15]=2

Participants

5

Reactant 4

HCID 7748Ethyl bromoacetateHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 22034371HCID 22034371, compound

Product 1

HCID 123817435HCID 123817435, compound

Procedure

To a stirred solution of sodium hydride (45 mg of 60% dispersion in mineral oil) in dry tetrahydrofuran (10 ml) was added 3-[(4-chlorophenyl)thio]-2-methyl-6-(methylsulfonyl)-1H-indole (160 mg) (the product of Example 20 step i). After 30 minutes the reaction was treated with ethyl bromoacetate (78 μl) and stirring continued for 1 hour. Reaction was quenched with ethanol, the solvent was removed in vacuo, the residue redissolved in ethyl acetate, washed with water, dried (MgSO4), and evaporated in vacuo and the residue purified by flash column chromatography eluting with 30% ethyl acetate and iso-hexane mixture. The sub-title compound was obtained as a white solid (180 mg).

Workup

  1. customReaction
  2. customwas quenched with ethanol
  3. customthe solvent was removed in vacuo
  4. dissolutionthe residue redissolved in ethyl acetate
  5. washwashed with water
  6. dry with materialdried (MgSO4)
  7. customevaporated in vacuo
  8. customthe residue purified by flash column chromatography
  9. washeluting with 30% ethyl acetate and iso-hexane mixture

Sources & evidence

ORD record
ord-16c3b861494c4e8c917cee12648ff35a
Source dataset
uspto-grants-2007_01
Patent number
US07166607B2

Reaction notes

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