Sodium hydride → HCID 21468829, compound

HRID 976582Notes

Reaction equation

HRID 976582 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-4f189fe6aece4050a6c90bb8850489aa
Source dataset
uspto-grants-1997_03
Patent number
US05612360

Reaction notes

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