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Potassium Carbonate → 5-Methylsulfonyl-2-[5-(4-acetylenyl-phenyl)-3-trifluoromethyl-1h-pyrazol-1-yl]pyridine

HRID 1634277
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HRID 1634277 반응식
[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[C:15]([C:16]3[CH:21]=[CH:20][C:19](Br)=[CH:18][CH:17]=3)=[CH:14][C:13]([C:23]([F:26])([F:25])[F:24])=[N:12]2)=[N:9][CH:10]=1)(=[O:4])=[O:3].C[Si]([C:31]#[CH:32])(C)C.C(OCC)(=O)C.CCCCCC.C(=O)([O-])[O-].[K+].[K+]>C(N(CC)CC)C.CO.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>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[C:15]([C:16]3[CH:21]=[CH:20][C:19]([C:31]#[CH:32])=[CH:18][CH:17]=3)=[CH:14][C:13]([C:23]([F:26])([F:25])[F:24])=[N:12]2)=[N:9][CH:10]=1)(=[O:4])=[O:3]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 11430Potassium CarbonateHCID 66111TrimethylsilylacetyleneHCID 99114082-[5-(4-Bromo-phenyl)-3-trifluoromethyl-pyrazol-1-yl]-5-methanesulfonyl-pyridineHCID 21226206Ethyl acetate hexane

생성물 1

HCID 102004535-Methylsulfonyl-2-[5-(4-acetylenyl-phenyl)-3-trifluoromethyl-1h-pyrazol-1-yl]pyridine

시약·촉매·용매 3

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 887Methanol용매
HCID 8471Triethylamine용매

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온도
80 °C

실험 절차

5-Methylsulfonyl-2-[5-(4-bromophenyl)-3-trifluoromethyl-1H-pyrazol-1-yl]pyridine (230 mg), Cul (5 mg), Pd(PPh3)4 (30 mg) were mixed in triethylamine (2.5 mL), followed by the addition of trimethylsilyl acetylene (0.182 mL), and the reaction mixture was heated at 80° C. for 2 hours. TLC in 1:1 of ethyl acetate/hexane showed complete conversion of the starting material to the product. The solvent was removed in vacuo to give the crude product. This crude material was then dissolved in methanol (2.5 mL), followed by the addition of potassium carbonate (20 mg). The reaction mixture was stirred at room temperature for 30 minutes. After filtration, the solvent was removed in vacuo to give the crude product which was purified by flash chromatography using 70:30 of methylene chloride/hexane to give the title compound (41 mg).

후처리

  1. customThe solvent was removed in vacuo
  2. customto give the crude product
  3. filtrationAfter filtration
  4. customthe solvent was removed in vacuo
  5. customto give the crude product which
  6. customwas purified by flash chromatography

출처 및 근거

ORD 기록
ord-931cdfa55cc94e0abc5cd70cac543923
출처 데이터셋
uspto-grants-2003_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06506779B1

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