3-(1-oxo-4-carboxybutyl)-N-(3-pyridyl)-indole → 5-[1-(Pyridin-3-yl)-1H-indol-3-yl]pentanoic acid

HRID 64683Notes

Reaction equation

HRID 64683 reaction equation
O=[C:2]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[CH:10]=1)[CH2:3][CH2:4][CH2:5][C:6]([OH:8])=[O:7]>C(O)(=O)C>[C:6]([CH2:5][CH2:4][CH2:3][CH2:2][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[CH:10]=1)([OH:8])=[O:7]

Participants

3

Reactant 1

HCID 136726973-(1-oxo-4-carboxybutyl)-N-(3-pyridyl)-indole

Product 1

HCID 134903525-[1-(Pyridin-3-yl)-1H-indol-3-yl]pentanoic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 0.5 g of 3-(1-oxo-4-carboxybutyl)-N-(3-pyridyl)-indole in 7.5 ml of glacial acetic acid is added 0.5 g of borane-tert-butylamine complex. The reaction mixture is stirred at room temperature overnight. The reaction mixture is concentrated, the residue is dissolved in 10 ml of 1N sodium hydroxide, water is added to the residue, the pH is adjusted to 5.0 with hydrochloric acid and the product is filtered off and dried to yield 3-(4-carboxybutyl)-N-(3-pyridyl)-indole identical to the compound obtained in Example 3b.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. dissolutionthe residue is dissolved in 10 ml of 1N sodium hydroxide
  3. additionwater is added to the residue
  4. filtrationthe product is filtered off
  5. customdried

Sources & evidence

ORD record
ord-a7924439a9494912a45e5d106a437e48
Source dataset
uspto-grants-1986_09
Patent number
US04609733

Reaction notes

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