Cesium carbonate → HCID 86711927, compound

HRID 1475235Notes

Reaction equation

HRID 1475235 reaction equation
[CH3:1][C:2]1[NH:6][N:5]=[C:4]([C:7]2[O:11][N:10]=[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)[N:8]=2)[N:3]=1.Br[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([N+:31]([O-:33])=[O:32])[CH:26]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O>[CH3:1][C:2]1[N:6]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([N+:31]([O-:33])=[O:32])[CH:26]=2)[N:5]=[C:4]([C:7]2[O:11][N:10]=[C:9]([C:12]3[CH:13]=[CH:14][C:15]([O:18][C:19]([F:22])([F:20])[F:21])=[CH:16][CH:17]=3)[N:8]=2)[N:3]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 77568Benzene, 1-(bromomethyl)-3-nitro-HCID 867118775-(5-methyl-1H-1,2,4-triazol-3-yl)-3-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazole2×

Product 1

HCID 86711927HCID 86711927, compoundYield 62.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-(5-methyl-1H-1,2,4-triazol-3-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole (Intermediate B, 2 g, 6.43 mmol), 1-(bromomethyl)-3-nitrobenzene (1.39 g, 6.43 mmol) and Cs2CO3 (4.2 g, 12.9 mmol) in DMF (40 mL) was stirred at RT for 16 h. The mixture was then diluted with H2O and extracted with EtOAc (3×200 mL). The combined organic extracts were washed with H2O (20 mL) and brine (20 mL), dried (Na2SO4), and concentrated under reduced pressure to afford the title compound as a yellow solid (1.8 g, 56.4%). LC-MS (ES+) C19H13F3N6O4 requires: 446. found: 447 (M+H)+.

Workup

  1. extractionextracted with EtOAc (3×200 mL)
  2. washThe combined organic extracts were washed with H2O (20 mL) and brine (20 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1f10b4b61f6e423c9cfb6d39e21fe9d8
Source dataset
uspto-grants-2015_04
Patent number
US09018380B2

Reaction notes

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