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Water → HCID 9865354, compound

HRID 497816
Notes
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Reaction equation

HRID 497816 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]#[N:22])[C:5](=[O:14])[N:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:7]=1.[N+:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1B(O)O)([O-:25])=[O:24].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[C:21]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:4]1[C:5](=[O:14])[N:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:7]=[C:2]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[N+:23]([O-:25])=[O:24])[CH:3]=1)#[N:22]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 2773548(2-Nitrophenyl)boronic acidHCID 223189902-(5-Bromo-1,2-dihydro-2-oxo-1-phenyl-3-pyridinyl)benzonitrile

Product 1

HCID 9865354HCID 9865354, compoundYield 31.2%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
120 °C

Procedure

5-Bromo-3-(2-cyanophenyl)-1-phenyl-1,2-dihydropyridin-2-one (100 mg), 60 mg of 2-nitrophenylboronic acid and 130 mg of cesium carbonate were suspended in 10 ml of dimethylformamide, then 20 mg of tetrakistriphenylphosphine palladium were added and the mixture was stirred at 120° C. in a nitrogen atmosphere for 4 hours. After allowing to cool, the reaction solution was poured into water, the mixture was extracted with ethyl acetate, the extract was dried over anhydrous magnesium sulfate, the solvent was evaporated in vacuo and the residue was purified by a silica gel column chromatography (hexane-ethyl acetate system) to give 35 mg of the title compound.

Workup

  1. temperatureto cool
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialthe extract was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated in vacuo
  5. customthe residue was purified by a silica gel column chromatography (hexane-ethyl acetate system)

Sources & evidence

ORD record
ord-cf6998b2345847af95328379c836a840
Source dataset
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06949571B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes