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

HRID 1754564노트

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HRID 1754564 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 86679809HCID 86679809, 화합물수율 73%

시약·촉매·용매 1

HCID 73012-Methyltetrahydrofuran용매

반응 조건

온도
65 °C

실험 절차

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%).

후처리

  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%)

출처 및 근거

ORD 기록
ord-fb59ea5c5daf44cda5d080e11c659602
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09169246B2

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