5-Methyl-2-(tri-n-butylstannyl)pyridine → 3-(5-Methylpyridin-2-yl)-N-((6-methylpyridin-3-yl)methyl)-5-(methylsulfonyl)benzamide

HRID 1845221Notes

Reaction equation

HRID 1845221 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([S:19]([CH3:22])(=[O:21])=[O:20])[CH:18]=1)[C:5]([NH:7][CH2:8][C:9]1[CH:10]=[N:11][C:12]([CH3:15])=[CH:13][CH:14]=1)=[O:6].[CH3:23][C:24]1[CH:25]=[CH:26][C:27]([Sn](CCCC)(CCCC)CCCC)=[N:28][CH:29]=1>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.C1(C)C=CC=CC=1>[CH3:23][C:24]1[CH:25]=[CH:26][C:27]([C:2]2[CH:3]=[C:4]([CH:16]=[C:17]([S:19]([CH3:22])(=[O:21])=[O:20])[CH:18]=2)[C:5]([NH:7][CH2:8][C:9]2[CH:10]=[N:11][C:12]([CH3:15])=[CH:13][CH:14]=2)=[O:6])=[N:28][CH:29]=1

Participants

5

Reactant 2

HCID 111327115-Methyl-2-(tri-n-butylstannyl)pyridineHCID 581882653-Bromo-N-((6-methylpyridin-3-yl)methyl)-5-(methylsulfonyl)benzamide

Product 1

HCID 581880473-(5-Methylpyridin-2-yl)-N-((6-methylpyridin-3-yl)methyl)-5-(methylsulfonyl)benzamide

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 3-bromo-N-((6-methylpyridin-3-yl)methyl)-5-(methylsulfonyl)benzamide (71 mg, 0.18 mmol), 5-methyl-2-(tributylstannyl)pyridine (91 mg, 0.23 mmol), tetrakis(triphenylphosphine)palladium(0) (11 mg, 0.0093 mmol) and toluene (2.0 mL) under argon was subjected to microwave irradiation at 120° C. for 2 hours. The mixture was cooled to allow the product to precipitate. The solvent was discarded and the precipitated solids were rinsed with hexane and then purified by preparative HPLC (100×21.2 mm C18 column, 30-70% CH3CN/water[10 mM Et2NH]) to afford a white foam.

Workup

  1. customirradiation at 120° C. for 2 hours
  2. temperatureThe mixture was cooled
  3. customto precipitate
  4. washthe precipitated solids were rinsed with hexane
  5. custompurified by preparative HPLC (100×21.2 mm C18 column, 30-70% CH3CN/water[10 mM Et2NH])
  6. customto afford a white foam

Sources & evidence

ORD record
ord-b6ea032b039648c49375c1dbf284b3d9
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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