Sodium Carbonate → (E)-3-[1-(4-Pyridin-3-ylphenylsulfonyl)-1H-pyrrol-3-yl]-acrylic acid tert-butyl ester

HRID 1948646Notes

Reaction equation

HRID 1948646 reaction equation
BrC1C=CC(S([N:11]2[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/C(O)=O)=C2)(=O)=O)=CC=1.[C:21]([O:25][C:26](=[O:44])/[CH:27]=[CH:28]/[C:29]1[CH:33]=[CH:32][N:31]([S:34]([C:37]2[CH:42]=[CH:41][C:40](Br)=[CH:39][CH:38]=2)(=[O:36])=[O:35])[CH:30]=1)([CH3:24])([CH3:23])[CH3:22].N1C=CC=C(B(O)O)C=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd](Cl)Cl>[C:21]([O:25][C:26](=[O:44])/[CH:27]=[CH:28]/[C:29]1[CH:33]=[CH:32][N:31]([S:34]([C:37]2[CH:42]=[CH:41][C:40]([C:16]3[CH:17]=[N:11][CH:15]=[CH:14][CH:13]=3)=[CH:39][CH:38]=2)(=[O:36])=[O:35])[CH:30]=1)([CH3:24])([CH3:23])[CH3:22]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 66646304(E)-3-[1-(4-bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-acrylic acid tert-butyl ester2×HCID 68524810(E)-3-[1-(4-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]acrylic acid

Product 1

HCID 66646399(E)-3-[1-(4-Pyridin-3-ylphenylsulfonyl)-1H-pyrrol-3-yl]-acrylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 13169693Triphenylphosphine palladium dichlorideCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

0.18 g (E)-3-[1-(4-bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-acrylic acid tart-butyl ester (compound D4) and 62 mg 3-pyridylboronic acid are dissolved in 10 ml DME. A catalytic amount of bis-(triphenylphosphin-palladium (II)-chloride and 0.6 ml of an aqueous solution of sodium carbonate are added and the mixture is heated to reflux temperature overnight. The title compound is isolated by means of chromatography.

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux temperature overnight

Sources & evidence

ORD record
ord-8b96fb1f3d1e488cbe5a15f446aac6f1
Source dataset
uspto-grants-2013_03
Patent number
US08399505B2

Reaction notes

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