2-(Tributylstannyl)pyridine → (5-Bromo-2-methoxy-phenyl)-[6-(2,4-difluoro-phenylamino)-pyridin-3-yl]-methanol

HRID 896085Notes

Reaction equation

HRID 896085 reaction equation
[Br:1][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](CCCC)(CCCC)C1C=CC=CN=1)CCC>C1(C)C(C)=CC=CC=1.CC(OC)(C)C.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>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][CH3:26])=[C:6]([CH: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)[OH:9])[CH:7]=1

Participants

6

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 22349594(5-Bromo-2-methoxy-phenyl)-[6-(2,4-difluoro-phenylamino)-pyridin-3-yl]-methanone

Product 1

HCID 22349592(5-Bromo-2-methoxy-phenyl)-[6-(2,4-difluoro-phenylamino)-pyridin-3-yl]-methanolYield 40%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 7237O-XyleneSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

(5-Bromo-2-methoxy-phenyl)-[6-(2,4-difluoro-phenylamino)-pyridin-3-yl]-methanone (50 mg; 0.12 mmol), 2-tributylstannylpyridine (88 mg; 0.26 mmol) and PdCl2(PPh3)2 (25 mg; 0.035 mmol) are dissolved in xylene (2 ml) and refluxed for 4.5 hours. The reaction mixture is diluted with TBME and filtered through a bed of SiO2. The resulting solid is dissolved in ether, crystallized by adding hexanes and yields the title compound as yellowish crystals (20 mg; 40%).

Workup

  1. temperaturerefluxed for 4.5 hours
  2. filtrationfiltered through a bed of SiO2
  3. dissolutionThe resulting solid is dissolved in ether
  4. customcrystallized
  5. additionby adding hexanes

Sources & evidence

ORD record
ord-eb634b211c0340a788a827a95486882f
Source dataset
uspto-grants-2005_07
Patent number
US06919336B2

Reaction notes

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