Cesium carbonate → HCID 86711941, compound

HRID 1475250Notes

Reaction equation

HRID 1475250 reaction equation
[CH3:1][C:2]1[NH:6][N:5]=[C:4]([C:7]2[S:8][CH:9]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=3)[N:11]=2)[N:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[Cl:29][C:30]1[CH:35]=[C:34]([CH2:36]Cl)[CH:33]=[CH:32][N:31]=1>CN(C=O)C.O>[Cl:29][C:30]1[CH:35]=[C:34]([CH2:36][N:6]2[C:2]([CH3:1])=[N:3][C:4]([C:7]3[S:8][CH:9]=[C:10]([C:12]4[CH:13]=[CH:14][C:15]([O:18][C:19]([F:22])([F:20])[F:21])=[CH:16][CH:17]=4)[N:11]=3)=[N:5]2)[CH:33]=[CH:32][N:31]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 111265732-Chloro-4-(chloromethyl)pyridineHCID 86711940HCID 86711940, compound

Product 1

HCID 86711941HCID 86711941, compoundYield 50.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 2-(5-methyl-1H-1,2,4-triazol-3-yl)-4-(4-(trifluoromethoxy)phenyl)thiazole (3 g, 9.2 mmol) and Cs2CO3 (4.8 g, 13 mmol) in DMF (20 mL) was added 2-chloro-4-(chloromethyl)pyridine (2.1 g, 13 mmol). The mixture was stirred at RT for 16 h, then diluted with H2O (20 mL) and extracted with EtOAc (3×30 mL). The combined organic layers were washed with H2O (20 mL), concentrated under reduced pressure and the residue was purified by silica gel column chromatography (Petroleum ether:EtOAc=4:1) to afford the title compound as an oil (2.1 g, 50.6%).

Workup

  1. extractionextracted with EtOAc (3×30 mL)
  2. washThe combined organic layers were washed with H2O (20 mL)
  3. concentrationconcentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (Petroleum ether:EtOAc=4:1)

Sources & evidence

ORD record
ord-a0420c81a2f847c290599870b932a9e7
Source dataset
uspto-grants-2015_04
Patent number
US09018380B2

Reaction notes

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