Acetic Acid → 3-(4-ethoxycarbonylbutyl)N-(3-pyridyl)-indole

HRID 64682Notes

Reaction equation

HRID 64682 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>O1CCCC1>[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

4

Reactant 2

HCID 176Acetic AcidHCID 136726963-(1-oxo-4-ethoxycarbonylbutyl)-N-(3-pyridyl)indole

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.5 g of 3-(1-oxo-4-ethoxycarbonylbutyl)-N-(3-pyridyl)-indole in 25 ml of tetrahydrofuran is added 0.6 g of borane-tert-butylamine complex and 0.6 ml of glacial acetic acid. The reaction mixture is heated at 90° and monitored by high pressure liquid chromatography. When complete, the reaction mixture is evaporated under reduced pressure, water and methylene chloride are added, the pH is adjusted to 7-8 with sodium carbonate solution, the organic layer is separated, washed with water, dried and evaporated to dryness to yield 3-(4-ethoxycarbonylbutyl)-N-(3-pyridyl)-indole.

Workup

  1. temperatureThe reaction mixture is heated at 90°
  2. customWhen complete, the reaction mixture is evaporated under reduced pressure, water and methylene chloride
  3. additionare added
  4. customthe organic layer is separated
  5. washwashed with water
  6. customdried
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-89818bb2ff514bf08d39d4b140fbbecc
Source dataset
uspto-grants-1986_09
Patent number
US04609733

Reaction notes

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