Cesium carbonate → N-[5-(2-tert-butyl-pyridin-4-yl)-4-methyl-thiazol-2-yl]acetamide

HRID 1430111Notes

Reaction equation

HRID 1430111 reaction equation
[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([CH3:10])[N:9]=1)(=[O:3])[CH3:2].Cl[C:12]1[CH:17]=[CH:16][N:15]=[C:14]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:13]=1.F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:10][C:8]1[N:9]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[S:6][C:7]=1[C:12]1[CH:17]=[CH:16][N:15]=[C:14]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:13]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 280907N-(4-Methylthiazol-2-yl)acetamideHCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 580879812-(tert-Butyl)-4-chloropyridine

Product 1

HCID 59293656N-[5-(2-tert-butyl-pyridin-4-yl)-4-methyl-thiazol-2-yl]acetamide

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2-acetamido-4-methylthiazole (92 mg), 4-chloro-2-tert.butylpyridine (83 mg), palladium acetate (10.4 mg), tri-tert-butylphosphonium tetrafluoroborate (28.3 mg) and cesium carbonate (319 mg) in DMF under an argon atmosphere is heated for 3 hours at 150° C. The reaction mixture is cooled, filtered through celite, evaporated and purified by normal and then reversed phase chromatography to give the title compound

Workup

  1. temperatureThe reaction mixture is cooled
  2. filtrationfiltered through celite
  3. customevaporated
  4. custompurified by normal and

Sources & evidence

ORD record
ord-6e32cceaf07d4400bef12ad6e3f9d47d
Source dataset
uspto-grants-2015_01
Patent number
US08940771B2

Reaction notes

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