2,2,2-Trifluoroethyl trifluoromethanesulfonate → HCID 86679809, compound

HRID 1754564Notes

Reaction equation

HRID 1754564 reaction equation
[Cl:1][C:2]1[C:3]([F:23])=[CH:4][C:5]([I:22])=[C:6]([NH:8][C:9]([C:11]2[CH:12]=[N:13][N:14]([CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][O:17]3)[CH:15]=2)=[O:10])[CH:7]=1.CC(C)([O-])C.[K+].FC(F)(F)S(O[CH2:36][C:37]([F:40])([F:39])[F:38])(=O)=O.C([O-])(O)=O.[Na+]>CC1OCCC1>[Cl:1][C:2]1[C:3]([F:23])=[CH:4][C:5]([I:22])=[C:6]([N:8]([CH2:36][C:37]([F:40])([F:39])[F:38])[C:9]([C:11]2[CH:12]=[N:13][N:14]([CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][O:17]3)[CH:15]=2)=[O:10])[CH:7]=1

Participants

6

Reactant 4

HCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 516892Sodium BicarbonateHCID 23665647Potassium tert-butoxideHCID 86679808HCID 86679808, compound

Product 1

HCID 86679809HCID 86679809, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 73012-MethyltetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of N-(5-chloro-4-fluoro-2-iodophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-4-carboxamide (1.26 g, 3.13 mmol) in 55 mL of anhydrous MeTHF heated to 65° C. are added potassium t-butoxide (421 mg, 3.76 mmol) and 2,2,2-trifluoroethyl trifluoromethanesulfonate (0.54 mL, 3.76 mmol). The reaction mixture is stirred for 2 hours at 65° C., and then cooled, poured into saturated aqueous NaHCO3 solution and extracted with EtOAc. The organic phase is washed with saturated aqueous NaCl solution, dried over Na2SO4 and concentrated to dryness. After purification by flash chromatography on silica (DCM/EtOAc: 100/0 to 95/5), 2.32 g of an orange-coloured solid are obtained (yield: 73%).

Workup

  1. temperaturecooled
  2. extractionextracted with EtOAc
  3. washThe organic phase is washed with saturated aqueous NaCl solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness
  6. customAfter purification by flash chromatography on silica (DCM/EtOAc: 100/0 to 95/5), 2.32 g of an orange-coloured solid
  7. customare obtained (yield: 73%)

Sources & evidence

ORD record
ord-fb59ea5c5daf44cda5d080e11c659602
Source dataset
uspto-grants-2015_10
Patent number
US09169246B2

Reaction notes

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