Water → N-[5-(3,4-dimethylphenyl)pyridin-3-yl]benzamide

HRID 876236Notes

Reaction equation

HRID 876236 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[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][C:23]=1[CH3:24].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[CH:19]=[C:20]([C:2]2[CH:3]=[C:4]([NH:8][C:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:16])[CH:5]=[N:6][CH:7]=2)[CH:21]=[CH:22][C:23]=1[CH3:24]

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27343483,4-Dimethylphenylboronic acidHCID 66701388N-(5-bromopyridin-3-yl)benzamide

Product 1

HCID 66701346N-[5-(3,4-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., 4.5 g (16.2 mmol) of N-(5-bromopyridin-3-yl)benzamide, 3.0 g (19.5 mmol) of (3,4-dimethylphenyl)boronic acid and 4.5 g (32.5 mmol) of potassium carbonate were dissolved in 59 ml of 1,2-dimethoxyethane, 19 ml of water and 117 ml of DMF. The mixture was flushed with argon, 0.1 g (0.08 mmol) of tetrakis(triphenylphosphine)palladium(0) was 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 and purified by column chromatography on silica gel (dichloromethane/methanol 100:1→100:4).

Workup

  1. additionwas 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
  6. custompurified by column chromatography on silica gel (dichloromethane/methanol 100:1→100:4)

Sources & evidence

ORD record
ord-f4d9172d2e114b15a69ab834d5dee900
Source dataset
uspto-grants-2015_03
Patent number
US08987248B2

Reaction notes

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