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Cesium carbonate → HCID 178497098, compound

HRID 931399
Notes
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Reaction equation

HRID 931399 reaction equation
Br[C:2]1[C:3]([NH:9][C:10](=[O:25])[C:11](=[CH2:24])[CH:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([O:22][CH3:23])=[O:21])=[CH:16][CH:15]=2)[CH3:13])=[N+:4]([O-:8])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:23][O:22][C:20]([C:17]1[CH:16]=[C:15]2[C:14](=[CH:19][CH:18]=1)[CH:12]([CH3:13])[C:11]1([C:2]3[C:3](=[N+:4]([O-:8])[CH:5]=[CH:6][CH:7]=3)[NH:9][C:10]1=[O:25])[CH2:24]2)=[O:21]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 10796Cesium carbonateHCID 178459998HCID 178459998, compound

Product 1

HCID 178497098HCID 178497098, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

Bis(triphenylphosphine)palladium(II) dichloride (0.17 g, 0.24 mmol) was added to a deoxygenated mixture of 3-bromo-2-(3-(4-(methoxycarbonyl)phenyl)-2-methylenebutanamido)pyridine 1-oxide (2.0 g, 5.0 mmol), cesium carbonate (4.03 g, 12.4 mmol) in anhydrous DMF (40 mL). The resulting mixture was heated at 110° C. under nitrogen for 20 h, then cooled and filtered through Celite®. The filter cake was washed with ethyl acetate. The filtrate was concentrated, and partitioned between ethyl acetate and brine (2×). The combined organic layers were dried over anhydrous sodium sulfate and concentrated to give the title compound which was used without further purification in next step.

Workup

  1. temperaturecooled
  2. filtrationfiltered through Celite®
  3. washThe filter cake was washed with ethyl acetate
  4. concentrationThe filtrate was concentrated
  5. custompartitioned between ethyl acetate and brine (2×)
  6. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-790f850ee3f84e9fb2f44123c45e04ef
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09296750B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes