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Potassium Carbonate → 2-{4-[3,5-Dimethyl-4-(4-methylphenyl)-1H-pyrazol-1-yl]phenyl}ethanol

HRID 891075
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HRID 891075 반응식
I[C:2]1[C:3]([CH3:17])=[N:4][N:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][OH:16])=[CH:10][CH:9]=2)[C:6]=1[CH3:7].B(O)(O)[C:19]1[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=1.C([O-])([O-])=O.[K+].[K+]>C(COC)OC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:17][C:3]1[C:2]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)=[C:6]([CH3:7])[N:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][OH:16])=[CH:10][CH:9]=2)[N:4]=1
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참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 79799Tolylboronic acidHCID 222445592-[4-(4-Iodo-3,5-dimethyl-1H-pyrazol-1-yl)phenyl]ethanol

생성물 1

HCID 222445852-{4-[3,5-Dimethyl-4-(4-methylphenyl)-1H-pyrazol-1-yl]phenyl}ethanol

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매
HCID 8071
1,2-Dimethoxyethane
용매

실험 절차

To a suspension of 2-[4-(4-iodo-3,5-dimethyl-1H-pyrazol-1-yl)phenyl]ethanol (step 2 of Example 11, 300 mg, 0.88 mmol) and p-tolylboronic acid (313 mg, 2.3 mmol) in dimethoxyethane (6.3 mL) were added 2 M aqueous K2CO3 (2.2 mL, 4.4 mmol) and bis(triphenylphosphine)palladium(II) chloride (124 mg, 0.18 mmol), and the mixture were refluxed for 16 h. The mixture was filtered through a pad of Celite and the filtrate was concentrated to give brown oil. It was partitioned between dichloromethane and water. The separated organic layer was dried (Na2SO4), evaporated, and purified by TLC with hexane/ethyl acetate (1:1) to afford 349 mg (quant.) of the title compound as white solids: MS (ESI) m/z 307 [M+H]+, 1H-NMR (CDCl3) δ 7.43-7.20 (8H, m), 3.87 (2H, t, J=6.4 Hz), 2.91 (2H, t, J=6.4 Hz), 2.40 (3H, s), 2.31 (3H, s), 2.28 (3H, s).

후처리

  1. temperaturethe mixture were refluxed for 16 h
  2. filtrationThe mixture was filtered through a pad of Celite
  3. concentrationthe filtrate was concentrated
  4. customto give brown oil
  5. customIt was partitioned between dichloromethane and water
  6. dry with materialThe separated organic layer was dried (Na2SO4)
  7. customevaporated
  8. custompurified by TLC with hexane/ethyl acetate (1:1)

출처 및 근거

ORD 기록
ord-6f18d4f98fa448e5b29bf5003383b6ab
출처 데이터셋
uspto-grants-2006_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07001917B2

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