Water → HCID 66652937、化合物

HRID 2283640

反応式

HRID 2283640 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]=1B(O)O.Br[C:17]1[C:18]([N+:28]([O-:30])=[O:29])=[N:19][N:20]([CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][O:23]2)[CH:21]=1.BrC1C=NN(C2CCCCO2)C=1[N+]([O-])=O.O>COCCOC.C(=O)([O-])[O-].[K+].[K+].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>[N+:28]([C:18]1[C:17]([C:3]2[CH:4]=[C:5]([O:8][C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:7][C:2]=2[OH:1])=[CH:21][N:20]([CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][O:23]2)[N:19]=1)([O-:30])=[O:29]

参加物

8

反応物 4

HCID 962WaterHCID 666527944-bromo-3-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazoleHCID 666531524-bromo-5-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazoleHCID 66655615HCID 66655615、化合物

生成物 1

HCID 66652937HCID 66652937、化合物

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 80711,2-Dimethoxyethane溶媒HCID 11430Potassium Carbonate溶媒

反応条件

温度
80 °C

実験手順

To a solution of 2-hydroxy-5-(trifluoromethoxy)phenylboronic acid (Preparation 23, 20.5 g, 92.4 mmol) and 4-bromo-3-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole or 4-bromo-5-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole (Preparation 22, 22.7 g, 82.2 mmol) in 1,2-dimethoxyethane (300 mL) and 2 M potassium carbonate in water (117 mL, 212 mmol) was added tetrakis(triphenylphosphine)palladium(0) (5.0 g, 4.3 mmol). The solution was sparged with argon (×3) and heated at 80° C. for 8 hours. The reaction mixture was cooled to ambient temperature and the layers separated. The aqueous phase was washed with ethyl acetate (×2). The combined organic phase was dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (0 to 30% ethyl acetate in hexanes gradient elution) and concentrated in vacuo. Excess hexanes was added to the residue and the resulting solid was collected by filtration and dried in vacuo to afford the title compound as off white crystals (19.5 g).

後処理

  1. customThe solution was sparged with argon (×3)
  2. temperatureThe reaction mixture was cooled to ambient temperature
  3. customthe layers separated
  4. washThe aqueous phase was washed with ethyl acetate (×2)
  5. dry with materialThe combined organic phase was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (0 to 30% ethyl acetate in hexanes gradient elution)
  8. concentrationconcentrated in vacuo
  9. additionExcess hexanes was added to the residue
  10. filtrationthe resulting solid was collected by filtration
  11. customdried in vacuo

出典と根拠

ORDレコード
ord-1ef9ecefa3de4463937a3de935c4744e
出典データセット
uspto-grants-2015_09
特許番号
US09145407B2

関連ノート

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