Sodium hydride → HCID 21468829, compound

HRID 743887Notes

Reaction equation

HRID 743887 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[CH:12]2)#[N:2].[H-].[Na+].Br[CH:21]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:22]([O:24][CH2:25][CH3:26])=[O:23]>C1COCC1>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH:21]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:13]=[CH:12]2)#[N:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 95580Ethyl 2-bromooctanoateHCID 21468934HCID 21468934, compound

Product 1

HCID 21468829HCID 21468829, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

5-(2-Cyanophenyl)indole (5.04 mmoles, 1.1 g) in 70 ml THF was treated with sodium hydride (255 mg, 50% in mineral oil) and stirred at 0° C. for 30 minutes. Ethyl 2-bromooctanoate (5.5 mmoles) in 40 ml THF was added dropwise. The reaction was stirred at room temperature for 4 hours, cooled, poured onto ice, extracted with ethyl acetate. The organic phase was dried and concentrated. The intermediate was chromatographed over silica gel eluted with 20% ether in hexane. The reaction yielded 1.1 g of ethyl 2-[5-(2-cyanophenyl)indol-1-yl]octanoate. (MS)

Workup

  1. stirringThe reaction was stirred at room temperature for 4 hours
  2. temperaturecooled
  3. additionpoured onto ice
  4. extractionextracted with ethyl acetate
  5. customThe organic phase was dried
  6. concentrationconcentrated
  7. customThe intermediate was chromatographed over silica gel
  8. washeluted with 20% ether in hexane

Sources & evidence

ORD record
ord-59533998be76450498c8e57c3eecb5ba
Source dataset
uspto-grants-1996_09
Patent number
US05556981

Reaction notes

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