Cesium carbonate → HCID 86711949, compound

HRID 1475257Notes

Reaction equation

HRID 1475257 reaction equation
[CH3:1][C:2]1[NH:6][N:5]=[C:4]([C:7]2[O:8][C:9]([C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=3)=[CH:10][N:11]=2)[N:3]=1.[Cl:23][C:24]1[CH:29]=[C:28]([CH2:30]Cl)[CH:27]=[CH:26][N:25]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O>[Cl:23][C:24]1[CH:29]=[C:28]([CH2:30][N:6]2[C:2]([CH3:1])=[N:3][C:4]([C:7]3[O:8][C:9]([C:12]4[CH:13]=[CH:14][C:15]([O:18][C:19]([F:22])([F:20])[F:21])=[CH:16][CH:17]=4)=[CH:10][N:11]=3)=[N:5]2)[CH:27]=[CH:26][N:25]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 111265732-Chloro-4-(chloromethyl)pyridineHCID 86711948HCID 86711948, compound

Product 1

HCID 86711949HCID 86711949, compoundYield 27.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(5-methyl-1H-1,2,4-triazol-3-yl)-5-(4-(trifluoromethoxy)phenyl)oxazole (260 mg, 0.83 mmol), 2-chloro-4-(chloromethyl)pyridine (270 mg, 1.66 mmol) and Cs2CO3 (820 mg, 2.5 mmol) in dry DMF (5 mL) was stirred at RT for 72 h. The mixture was then diluted with H2O (50 mL) and extracted with DCM/MeOH (20/1 v/v, 4×50 mL). The combined organic layers were washed with H2O (3×40 mL), brine (50 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to give the crude product, which was purified by silica gel chromatography (DCM:MeOH=20:1 to 15:1) to afford the title compound as a white solid (100 mg, 27%). MS (ES+) C19H13ClF3N5O2 requires: 435. found: 436 [M+H]+.

Workup

  1. extractionextracted with DCM/MeOH (20/1 v/v, 4×50 mL)
  2. washThe combined organic layers were washed with H2O (3×40 mL), brine (50 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto give the crude product, which
  7. customwas purified by silica gel chromatography (DCM:MeOH=20:1 to 15:1)

Sources & evidence

ORD record
ord-c0513111d25a435da5ac1987e706288f
Source dataset
uspto-grants-2015_04
Patent number
US09018380B2

Reaction notes

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