Water → Ethyl 4-{5-[(phenylcarbonyl)amino]pyridin-3-yl}benzenecarboxylate

HRID 876243Notes

Reaction equation

HRID 876243 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.[CH2:17]([O:19][C:20]([C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1)=[O:21])[CH3:18].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>[C:10]1([C:9]([NH:8][C:4]2[CH:3]=[C:2]([C:25]3[CH:26]=[CH:27][C:22]([C:20]([O:19][CH2:17][CH3:18])=[O:21])=[CH:23][CH:24]=3)[CH:7]=[N:6][CH:5]=2)=[O:16])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27343504-Ethoxycarbonylphenylboronic acidHCID 66701388N-(5-bromopyridin-3-yl)benzamide

Product 1

HCID 66761533Ethyl 4-{5-[(phenylcarbonyl)amino]pyridin-3-yl}benzenecarboxylate

Reagents, catalysts & solvents 3

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

Conditions

Temperature
85 °C

Procedure

At 50° C., 5.14 g (18.2 mmol) of N-(5-bromopyridin-3-yl)benzamide, 5.40 g (27.8 mmol) of 4-ethoxycarbonylphenylboronic acid and 5.03 g (36.4 mmol) of potassium carbonate were dissolved in 30 ml of 1,2-dimethoxyethane, 9 ml of water and 65 ml of DMF. The mixture was flushed with argon, 105 mg (0.09 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 (cyclohexane/ethyl acetate 2:1→1:1). The separated solid and the appropriate fraction from the chromatography were combined. Yield: 4.6 g (60% 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 (cyclohexane/ethyl acetate 2:1→1:1)

Sources & evidence

ORD record
ord-a1229c04aa9a4bc0984dc7f9344e5eba
Source dataset
uspto-grants-2015_03
Patent number
US08987248B2

Reaction notes

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