Water → HCID 67452962、化合物

HRID 1754565ノート

反応式

HRID 1754565 の反応式
C([O-])(=[O:3])C.[K+].Cl[C:7]1[C:8](F)=[CH:9][C:10](I)=[C:11](N(CC(F)(F)F)C(C2C=NN([CH:21]3[CH2:26]C[CH2:24][CH2:23][O:22]3)C=2)=O)[CH:12]=1.O>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=1.[CH3:26][C:21](=[O:3])[O:22][CH2:23][CH3:24]

参加物

6

反応物 3

HCID 962WaterHCID 517044Potassium Acetate2 回HCID 86679809HCID 86679809、化合物

生成物 1

HCID 67452962HCID 67452962、化合物収率 57%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒2 回HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

The catalyst Pd(PPh3)4 (630 mg, 0.55 mmol) and potassium acetate (890 mg, 9.0 mmol) are added to a solution of N-(5-chloro-4-fluoro-2-iodophenyl)-1-(tetrahydro-2H-pyran-2-yl)-N-(2,2,2-trifluoroethyl)-1H-pyrazole-4-carboxamide (2,2 g, 4.5 mmol) in 10 mL of anhydrous DMF placed in a microwave reactor under nitrogen. The reactor is sealed and the reaction mixture is stirred for 15 minutes at 90° C. under microwave irradiation. A further amount of catalyst Pd(PPh3)4 (630 mg, 0.55 mmol) and of potassium acetate (890 mg, 9.0 mmol) are added to the reaction medium, which is stirred for 15 minutes at 110° C. under microwave irradiation. The mixture is cooled, poured into water 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) and then (cyclohexene/EA: 90/10) and DCM (100%), 260 mg of a white solid are obtained (yield: 57%).

後処理

  1. customplaced in a microwave reactor under nitrogen
  2. customThe reactor is sealed
  3. stirringis stirred for 15 minutes at 110° C. under microwave irradiation
  4. temperatureThe mixture is cooled
  5. extractionextracted with EtOAc
  6. washThe organic phase is washed with saturated aqueous NaCl solution
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated to dryness
  9. customAfter purification by flash chromatography on silica (DCM/EtOAc: 100/0 to 95/5)

出典と根拠

ORDレコード
ord-d33c42ef93c749de96468610fb02a12e
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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