Sodium hydride → HCID 131726208, compound

HRID 1374790Notes

Reaction equation

HRID 1374790 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([S:10][C:11]2[C:19]3[C:18]([C:20]#[N:21])=[C:17]([CH3:22])[CH:16]=[CH:15][C:14]=3[NH:13][C:12]=2[CH3:23])=[CH:6][CH:5]=1.Br[CH2:25][C:26]([O:28][CH3:29])=[O:27]>O1CCCC1>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([S:10][C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([CH3:22])[C:18]=3[C:20]#[N:21])[N:13]([CH2:25][C:26]([O:28][CH3:29])=[O:27])[C:12]=2[CH3:23])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 210778313-[(4-Chlorophenyl)sulfanyl]-2,5-dimethyl-1H-indole-4-carbonitrile

Product 1

HCID 131726208HCID 131726208, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of sodium hydride (96.1 mg of 60% dispersion in mineral oil) in dry tetrahydrofuran (15 ml) was added 3-[(4-chlorophenyl)thio]-2,5-dimethyl-1H-indole-4-carbonitrile (400 mg) in dry tetrahydrofuran (5 ml). After 30 minutes the reaction was treated with methyl bromoacetate (177 μl) and stirring continued for 4 hours. The solvent was removed in vacuo, the residue redissolved in ethyl acetate, washed with water, brine, dried (MgSO4), evaporated in vacuo and the residue purified by flash column chromatography eluting with 1:1 ethyl acetate and iso-hexane mixture. The sub-title compound was obtained as a yellow solid (360 mg).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue redissolved in ethyl acetate
  3. washwashed with water, brine
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo
  6. customthe residue purified by flash column chromatography
  7. washeluting with 1:1 ethyl acetate and iso-hexane mixture

Sources & evidence

ORD record
ord-7753c3b46f9b44ed9ae6238e11b9eea5
Source dataset
uspto-grants-2007_01
Patent number
US07166607B2

Reaction notes

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