Sodium hydride → HCID 21867441, compound

HRID 857330Notes

Reaction equation

HRID 857330 reaction equation
[CH3:1][S:2][C:3]1[C:4]2[C:5]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)=[C:6]([Br:12])[NH:7][C:8]=2[CH:9]=[CH:10][CH:11]=1.[H-].[Na+].Br[CH2:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:12][C:6]1[N:7]([CH2:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:8]2[C:4]([C:5]=1[CH2:13][C:14]1[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=1)=[C:3]([S:2][CH3:1])[CH:11]=[CH:10][CH:9]=2

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 76300Ethyl 4-bromobutyrateHCID 21867514HCID 21867514, compound

Product 1

HCID 21867441HCID 21867441, compoundYield 59.8%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the indole of Step 7 (800 mg, 2.4 mmol) in DMF (15 mL) was added NaH (136 mg, 3.4 mmol, 60% in oil) at 0° C. The reaction mixture was stirred at 0° C. for 15 minutes and tetra-n-butylammonium iodide (300 mg) was added, followed by the addition of ethyl 4-bromobutyrate (663 mg, 3.3 mmol). The resulting mixture was stirred for 2 h at r.t., quenched with saturated aqueous NH4Cl and extracted with EtOAc. The combined organic layers were washed with water and brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography eluted with 20% EtOAc in Hexanes to provide 690 mg of the title compound as a brown oil.

Workup

  1. stirringThe resulting mixture was stirred for 2 h at r.t.
  2. customquenched with saturated aqueous NH4Cl
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography
  8. washeluted with 20% EtOAc in Hexanes

Sources & evidence

ORD record
ord-ce5ccc5dcd8c4afc91df0c8440ac2e78
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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