Water → N-{5-[3-(Propan-2-yl)phenyl]pyridin-3-yl}benzenecarboxamide

HRID 876240Notes

Reaction equation

HRID 876240 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][CH:18]([C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][CH:25]=1)[CH3:19].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][CH:18]([C:20]1[CH:25]=[C:24]([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:23]=[CH:22][CH:21]=1)[CH3:19]

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27734783-Isopropylbenzeneboronic acidHCID 66701388N-(5-bromopyridin-3-yl)benzamide

Product 1

HCID 66701277N-{5-[3-(Propan-2-yl)phenyl]pyridin-3-yl}benzenecarboxamide

Reagents, catalysts & solvents 3

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

Conditions

Temperature
85 °C

Procedure

At 50° C., 1.4 g (4.9 mmol) of N-(5-bromopyridin-3-yl)benzamide, 1.0 g (5.9 mmol) of [3-(1-methylethyl)phenyl]boronic acid and 1.4 g (9.9 mmol) of potassium carbonate were dissolved in 15 ml of 1,2-dimethoxyethane, 5 ml of water and 30 ml of DMF. The mixture was flushed with argon, 29 mg (0.03 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 and then purified by preparative HPLC (Reprosil C18, water/acetonitrile gradient). Yield: 1.4 g (92% 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
  6. custompurified by preparative HPLC (Reprosil C18, water/acetonitrile gradient)

Sources & evidence

ORD record
ord-4bee21a2b3dc485c927446790a7d72c5
Source dataset
uspto-grants-2015_03
Patent number
US08987248B2

Reaction notes

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