Cesium carbonate → N-({6-[2-(pyridin-3-yl)-1,3-thiazol-5-yl]pyridin-2-yl}sulphonyl)acetamide

HRID 2359919Notes

Reaction equation

HRID 2359919 reaction equation
Br[C:2]1[N:7]=[C:6]([S:8]([NH:11][C:12](=[O:14])[CH3:13])(=[O:10])=[O:9])[CH:5]=[CH:4][CH:3]=1.[S:15]1[CH:19]=[CH:18][N:17]=[C:16]1[C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.Cl[Pd](Cl)(P(C(C)(C)C)(C(C)(C)C)O)P(O)(C(C)(C)C)C(C)(C)C>[N:22]1[CH:23]=[CH:24][CH:25]=[C:20]([C:16]2[S:15][C:19]([C:2]3[N:7]=[C:6]([S:8]([NH:11][C:12](=[O:14])[CH3:13])(=[O:10])=[O:9])[CH:5]=[CH:4][CH:3]=3)=[CH:18][N:17]=2)[CH:21]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 111827873-Thiazol-2-yl-pyridineHCID 86667250N-[(6-Bromopyridin-2-yl)sulphonyl]acetamide

Product 1

HCID 66634005N-({6-[2-(pyridin-3-yl)-1,3-thiazol-5-yl]pyridin-2-yl}sulphonyl)acetamide

Reagents, catalysts & solvents 2

HCID 178454906HCID 178454906, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

N-[(6-Bromopyridin-2-yl)sulphonyl]acetamide (0.112 g, 0.4 mmol), 3-(1,3-thiazol-2-yl)pyridine (0.065 g, 0.4 mmol, prepared by the methods described in WO 2010/006713), dichloro{bis[di-tert-butyl(hydroxy)phosphoranyl]}palladium (0.006 g, 0.012 mmol) and caesium carbonate (0.26 g, 0.8 mmol) were stirred in 10 ml of N,N-dimethylformamide at 120° C. under argon for 16 h. After cooling, the solvent was removed under reduced pressure and the residue was chromatographed (silica gel, dichloromethane/methanol eluent). This gave 0.024 g (15% of theory) of N-({6-[2-(pyridin-3-yl)-1,3-thiazol-5-yl]pyridin-2-yl}sulphonyl)acetamide.

Workup

  1. temperatureAfter cooling
  2. customthe solvent was removed under reduced pressure
  3. customthe residue was chromatographed (silica gel, dichloromethane/methanol eluent)

Sources & evidence

ORD record
ord-b94114dd2d15461187486d4b8d98c7dc
Source dataset
uspto-grants-2014_04
Patent number
US08686004B2

Reaction notes

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