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Cesium carbonate → HCID 71150135, compound

HRID 1466234
Notes
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Reaction equation

HRID 1466234 reaction equation
Br[C:2]1[CH:19]=[CH:18][C:5]([CH2:6][NH:7][C:8](=[O:17])[C:9]2[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:16])=[CH:4][C:3]=1[CH3:20].[O:21]=[C:22]1[CH:27]=[C:26](B(O)O)[CH:25]=[CH:24][NH:23]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[Cl:16][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]([Cl:15])[C:9]=1[C:8]([NH:7][CH2:6][C:5]1[CH:18]=[CH:19][C:2]([C:26]2[CH:25]=[CH:24][NH:23][C:22](=[O:21])[CH:27]=2)=[C:3]([CH3:20])[CH:4]=1)=[O:17]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 235469172-(Hydroxy)pyridine-4-boronic acidHCID 71149961HCID 71149961, compound

Product 1

HCID 71150135HCID 71150135, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
85 °C

Procedure

N-(4-Bromo-3-methylbenzyl)-2,6-dichlorobenzamide (0.13 g, 0.35 mmol), 2-oxo-1,2-dihydropyridin-4-ylboronic acid (0.053 g, 0.39 mmol), cesium carbonate (0.34 g, 1.05 mmol), [1,1′Bis(diphenylphosphino(ferrocene]dichloropalladium(II) (25 mg, 0.035 mmol) were dissolved in degassed DMF (3 mL) and H2O (1.5 mL). The reaction mixture was degassed again by bubbling nitrogen through for 15 min then heated in the microwave at 85° C. for 20 min The reaction mixture was diluted with EtOAc and extracted three times with water. The organic phase was dried over magnesium sulfate, filtered and concentrated in vacuum. The resulting solid was purified by reverse phase chromatography to afford 2,6-dichloro-N-(3-methyl-4-(2-oxo-1,2-dihydropyridin-4-yl)benzyl)benzamide.

Workup

  1. customThe reaction mixture was degassed again
  2. customby bubbling nitrogen through for 15 min
  3. additionwas diluted with EtOAc
  4. extractionextracted three times with water
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuum
  8. customThe resulting solid was purified by reverse phase chromatography

Sources & evidence

ORD record
ord-92a4f769f7f24cb585ee3d45d8e0a049
Source dataset
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09000015B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes