Ethyl Acrylate → HCID 53631951, compound

HRID 485360Notes

Reaction equation

HRID 485360 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)[CH:6]=[CH:5]2.[C:17]([O:21][CH2:22][CH3:23])(=[O:20])[CH:18]=[CH2:19].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(N(CC)CC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:22]([O:21][C:17]([CH:18]=[CH:19][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)[CH:6]=[CH:5]2)=[O:20])[CH3:23]

Participants

6

Reactant 3

HCID 8821Ethyl AcrylateHCID 80271Tri-o-tolylphosphineHCID 20270187HCID 20270187, compound

Product 1

HCID 53631951HCID 53631951, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Procedure

A solution of 0.75 g of 5-bromo-N-(3-pyridyl)indole and 0.5 g of ethyl acrylate in 20 ml of triethylamine is refluxed for 48 hours with 10.8 mg of palladium acetate and 30 mg of tri-o-tolylphosphine. The reaction mixture is cooled, evaporated and chromatographed on 20 g of silica gel with diethyl ether to yield 5-(2-ethoxycarbonylethenyl)-N-(3-pyridyl)indole. Saponification by refluxing for 15 hours in 30 ml of ethanol with 5 ml of 2N sodium hydroxide yields a solution which is evaporated to dryness. The residue is partitioned between 20 ml of ether and 10 ml of water. The aqueous phase is separated, brought to pH 5 and the resulting solid is filtered to yield 5-(2-carboxyethenyl)-N-(3-pyridyl)indole which melts with decomposition at 180°.

Workup

  1. temperatureThe reaction mixture is cooled
  2. customevaporated
  3. customchromatographed on 20 g of silica gel with diethyl ether

Sources & evidence

ORD record
ord-62810b30cb8a488dbaa27243c0f5ab5e
Source dataset
uspto-grants-1985_08
Patent number
US04536505

Reaction notes

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