2,2,2-Trifluoroethyl trifluoromethanesulfonate → HCID 86679809、化合物

HRID 1754564ノート

反応式

HRID 1754564 の反応式
[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

参加物

6

反応物 4

HCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 516892Sodium BicarbonateHCID 23665647Potassium tert-butoxideHCID 86679808HCID 86679808、化合物

生成物 1

HCID 86679809HCID 86679809、化合物収率 73%

試薬・触媒・溶媒 1

HCID 73012-Methyltetrahydrofuran溶媒

反応条件

温度
65 °C

実験手順

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%).

後処理

  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%)

出典と根拠

ORDレコード
ord-fb59ea5c5daf44cda5d080e11c659602
出典データセット
uspto-grants-2015_10
特許番号
US09169246B2

反応ノート

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