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Tri-o-tolylphosphine → 3-[2-Chloro-5-(methylsulfonyl)-3-pyridinyl]-1-(3,4-dichlorophenyl)propan-1-one

HRID 280196
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HRID 280196 반응식
[Cl:1][C:2]1[C:7](I)=[CH:6][C:5]([S:9]([CH3:12])(=[O:11])=[O:10])=[CH:4][N:3]=1.[CH:13]([CH:15]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=1)[OH:16])=[CH2:14].C(N(CC)C(C)C)(C)C.CC1C(P(C2C(C)=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.IC1C=CC=CN=1>C([O-])(=O)C.C([O-])(=O)C.[Pd+2].CN(C)C=O>[Cl:1][C:2]1[C:7]([CH2:14][CH2:13][C:15]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=2)=[O:16])=[CH:6][C:5]([S:9]([CH3:12])(=[O:11])=[O:10])=[CH:4][N:3]=1
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참가 물질

8

반응물 5

HCID 80271Tri-o-tolylphosphineHCID 81531DiisopropylethylamineHCID 2211262-IodopyridineHCID 135677651-(3,4-Dichlorophenyl)prop-2-en-1-olHCID 13567772HCID 13567772, 화합물

생성물 1

HCID 135677733-[2-Chloro-5-(methylsulfonyl)-3-pyridinyl]-1-(3,4-dichlorophenyl)propan-1-one

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

A mixture of 0.95 g of 2-chloro-3-iodo-5-(methylsulfonyl)pyridine, 0.91 g of α-ethenyl-3,4-dichlorobenzenemethanol, 0.77 g of N,N-diisopropylethylamine, 0.04 g of tri-o-tolyphosphine, 0.02 g of palladium diacetate and 3 ml of dimethylformamide was heated to 100° C. under nitrogen. The mixture was heated at this temperature for 20 minutes and then at 116° C. for an additional 20 minutes at which point thin layer chromatography showed no iodopyridine starting material. The mixture was then cooled and partitioned between 1N hydrochloric acid and methyl acetate. The ethyl acetate layer was washed twice with aqueous saturated sodium chloride solution, dried over magnesium sulfate and filtered and the filtrate was concentrated to a dark solid residue. Column chromatography of this residue (silica gel, 1:1 ethyl acetate/hexane) gave a pale yellow solid. This was recrystallized from ethanol/ethyl acetate to give 3-[2-chloro-5-(methylsulfonyl)-3-pyridinyl]-1-(3,4-dichlorophenyl)propan-1-one melting at about 128.5°-130.5° C.

후처리

  1. temperatureThe mixture was heated at this temperature for 20 minutes
  2. temperatureThe mixture was then cooled
  3. custompartitioned between 1N hydrochloric acid and methyl acetate
  4. washThe ethyl acetate layer was washed twice with aqueous saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated to a dark solid residue
  8. customColumn chromatography of this residue (silica gel, 1:1 ethyl acetate/hexane) gave a pale yellow solid
  9. customThis was recrystallized from ethanol/ethyl acetate

출처 및 근거

ORD 기록
ord-ce77784759be48a6b84093ab7095fa00
출처 데이터셋
uspto-grants-1986_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04588733

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