Sodium hydride → HCID 21867377, compound

HRID 857342Notes

Reaction equation

HRID 857342 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[C:4]([S:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)=[C:5]([C:12]([O:14][CH3:15])=[O:13])[NH:6]2.[H-].[Na+].Br[CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[C:4]([S:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)=[C:5]([C:12]([O:14][CH3:15])=[O:13])[N:6]2[CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 76300Ethyl 4-bromobutyrateHCID 21867540HCID 21867540, compound

Product 1

HCID 21867377HCID 21867377, compoundYield 78.8%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the indole of Step 1 (500 mg, 1.2 mmol) in DMF (10 mL) at 0° C. was added NaH (63 mg, 1.6 mmol, 60% in oil). 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 (360 mg, 1.8 mmol). The resulting mixture was stirred for 3 hours 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 30% EtOAc in Hexanes to provide 500 mg of the title compound as a solid.

Workup

  1. stirringThe resulting mixture was stirred for 3 hours 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 30% EtOAc in Hexanes

Sources & evidence

ORD record
ord-77fe032f138248e5bcf44cf214fbaaca
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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