Water → HCID 66652937, 화합물

HRID 2283640노트

반응식

HRID 2283640 반응식
[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]

참가 물질

8

반응물 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, 화합물

생성물 1

HCID 66652937HCID 66652937, 화합물

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매HCID 11430Potassium Carbonate용매

반응 조건

온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-1ef9ecefa3de4463937a3de935c4744e
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09145407B2

반응 노트

불러오는 중…