Dimethyl Sulfoxide → 3-(6-carboxyhex-1-enyl)-N-(3-pyridyl)indole

HRID 485346Notes

Reaction equation

HRID 485346 reaction equation
CS(C)=O.C([Li])CCC.[Br-].[C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:13])=[O:12].[N:38]1[CH:43]=[CH:42][CH:41]=[C:40]([N:44]2[C:52]3[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=3)[C:46]([CH:53]=O)=[CH:45]2)[CH:39]=1>O>[C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH:18]=[CH:53][C:46]1[C:47]2[C:52](=[CH:51][CH:50]=[CH:49][CH:48]=2)[N:44]([C:40]2[CH:39]=[N:38][CH:43]=[CH:42][CH:41]=2)[CH:45]=1)([OH:13])=[O:12]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 2779280(5-Carboxypentyl)triphenylphosphanium bromideHCID 13490349HCID 13490349, compoundHCID 178418339Butyllithium

Product 1

HCID 541584553-(6-carboxyhex-1-enyl)-N-(3-pyridyl)indole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of dimsyllithium (from 80 ml of dimethylsulfoxide and 13 ml of 2.1M n-butyllithium) is stirred under nitrogen at room temperature, and 6.2 g of 5-carboxypentyltriphenylphosphonium bromide is added in portions. The reaction mixture is stirred for 30 minutes and 3.0 g of N-(3-pyridyl)indole-3-carboxaldehyde is added. After 18 hours at room temperature, the reaction mixture is diluted with 240 ml of water and extracted with 100 ml of ethyl acetate. The aqueous phase is neutralized with 1.1 ml of concentrated hydrochloric acid and extracted with ethyl acetate. The extracts are dried over sodium sulfate and evaporated to an oil which is triturated with ether to give a semi-solid which is recrystallized from methanol to yield 3-(6-carboxyhex-1-enyl)-N-(3-pyridyl)indole, m.p. 124°-125°.

Workup

  1. waitAfter 18 hours at room temperature
  2. extractionextracted with 100 ml of ethyl acetate
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extracts are dried over sodium sulfate
  5. customevaporated to an oil which
  6. customis triturated with ether
  7. customto give a semi-solid which
  8. customis recrystallized from methanol

Sources & evidence

ORD record
ord-2dc8df6ce6464c01b10bdb1e35513d3e
Source dataset
uspto-grants-1985_08
Patent number
US04536505

Reaction notes

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