Pyridine, 4-(trimethylstannyl)- → [6-(2,4-Difluoro-phenylamino)-pyridin-3-yl]-(2-methoxy-5-pyridin-4-yl-phenyl)-methanone

HRID 896087Notes

Reaction equation

HRID 896087 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:25][CH3:26])=[C:6]([C:8]([C:10]2[CH:11]=[N:12][C:13]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[F:24])=[CH:14][CH:15]=2)=[O:9])[CH:7]=1.C[Sn](C)(C)[C:29]1[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=1>C1(C)C(C)=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:24][C:18]1[CH:19]=[C:20]([F:23])[CH:21]=[CH:22][C:17]=1[NH:16][C:13]1[N:12]=[CH:11][C:10]([C:8]([C:6]2[CH:7]=[C:2]([C:29]3[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=3)[CH:3]=[CH:4][C:5]=2[O:25][CH3:26])=[O:9])=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 11128458Pyridine, 4-(trimethylstannyl)-HCID 22349594(5-Bromo-2-methoxy-phenyl)-[6-(2,4-difluoro-phenylamino)-pyridin-3-yl]-methanone

Product 1

HCID 10202062[6-(2,4-Difluoro-phenylamino)-pyridin-3-yl]-(2-methoxy-5-pyridin-4-yl-phenyl)-methanoneYield 32%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 7237O-XyleneSolvent

Procedure

(5-Bromo-2-methoxy-phenyl)-[6-(2,4-difluoro-phenylamino)-pyridin-3-yl]-methanone (100 mg; 0.24 mmol), 4-trimethylstannylpyridine (115 mg; 0.47 mml) and PdCl2(PPh3)2 (50 mg; 0.07 mmol) are dissolved in xylene (2 ml) and refluxed under argon for 20 min. The reaction mixture is purified via chromatography (SiO2; acetone/hexanes 3/7) and yields the title compound as a colorless foam (32 mg; 32%).

Workup

  1. temperaturerefluxed under argon for 20 min
  2. customThe reaction mixture is purified via chromatography (SiO2; acetone/hexanes 3/7)

Sources & evidence

ORD record
ord-706df775ae754ca9ace24384291ab310
Source dataset
uspto-grants-2005_07
Patent number
US06919336B2

Reaction notes

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