3-(1-oxo-4-ethoxycarbonylbutyl)-N-(3-pyridyl)indole → 3-(4-ethoxycarbonylbutyl)N-(3-pyridyl)-indole

HRID 64680Notes

Reaction equation

HRID 64680 reaction equation
O=[C:2]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[CH:12]=1)[CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7]>C(O)(=O)C>[CH2:9]([O:8][C:6]([CH2:5][CH2:4][CH2:3][CH2:2][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[CH:12]=1)=[O:7])[CH3:10]

Participants

3

Reactant 1

HCID 136726963-(1-oxo-4-ethoxycarbonylbutyl)-N-(3-pyridyl)indole

Product 1

HCID 134903513-(4-ethoxycarbonylbutyl)N-(3-pyridyl)-indole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 5 g of 3-(1-oxo-4-ethoxycarbonylbutyl)-N-(3-pyridyl)indole in 75 ml of glacial acetic acid is added 5 g of borane-tert-butylamine complex. The reaction mixture is stirred at room temperature overnight. The reaction mixture is concentrated, water is added to the residue and the product is extracted with methylene chloride. The organic layer is separated, washed first with concentrated sodium carbonate solution, then with saturated sodium chloride solution, dried over sodium sulfate and evaporated to dryness to yield 3-(4-ethoxycarbonylbutyl)-N-(3-pyridyl)-indole, melting at 56°-58°.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. additionwater is added to the residue
  3. extractionthe product is extracted with methylene chloride
  4. customThe organic layer is separated
  5. washwashed first with concentrated sodium carbonate solution
  6. dry with materialwith saturated sodium chloride solution, dried over sodium sulfate
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-a0330ebff62d4923980afdc1940b5df1
Source dataset
uspto-grants-1986_09
Patent number
US04609733

Reaction notes

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