Water → N-[5-(2,3-dimethylphenyl)pyridin-3-yl]benzamide

HRID 876241Notes

Reaction equation

HRID 876241 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[N:6][CH:7]=1.[CH3:17][C:18]1[C:23]([CH3:24])=[CH:22][CH:21]=[CH:20][C:19]=1B(O)O.C(=O)([O-])[O-].[K+].[K+].O>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C=O)C>[CH3:17][C:18]1[C:23]([CH3:24])=[CH:22][CH:21]=[CH:20][C:19]=1[C:2]1[CH:3]=[C:4]([NH:8][C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:16])[CH:5]=[N:6][CH:7]=1

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27733952,3-Dimethylphenylboronic acidHCID 66701388N-(5-bromopyridin-3-yl)benzamide

Product 1

HCID 66701372N-[5-(2,3-dimethylphenyl)pyridin-3-yl]benzamide

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

At 50° C., 3.93 g (13.9 mmol) of N-(5-bromopyridin-3-yl)benzamide, 2.50 g (16.7 mmol) of (2,3-dimethylphenyl)boronic acid and 3.84 g (27.8 mmol) of potassium carbonate were dissolved in 50 ml of 1,2-dimethoxyethane, 17 ml of water and 100 ml of DMF. The mixture was flushed with argon, 81 mg (0.07 mmol) of tetrakis(triphenylphosphine)palladium(0) were added and the mixture was stirred at 85° C. for 12 h. The reaction mixture was concentrated slightly on a rotary evaporator, diluted with water and extracted with dichloromethane. The organic phase was concentrated under reduced pressure and the residue was triturated with methyl tert-butyl ether, the solid was filtered off and the filtrate was purified by column chromatography on silica gel (cyclohexane/ethyl acetate 2:1→1:1). The separated solid and the appropriate fraction from the chromatography were combined. Yield: 4.2 g (96% of theory)

Workup

  1. additionwere added
  2. concentrationThe reaction mixture was concentrated slightly on a rotary evaporator
  3. additiondiluted with water
  4. extractionextracted with dichloromethane
  5. concentrationThe organic phase was concentrated under reduced pressure
  6. customthe residue was triturated with methyl tert-butyl ether
  7. filtrationthe solid was filtered off
  8. customthe filtrate was purified by column chromatography on silica gel (cyclohexane/ethyl acetate 2:1→1:1)

Sources & evidence

ORD record
ord-dc96ab8968bc48d08acb7b07a9a48cce
Source dataset
uspto-grants-2015_03
Patent number
US08987248B2

Reaction notes

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