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Benzyl mercaptan → 3-(Benzylsulfanyl)-5-chloropyridine

HRID 869758
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인쇄 미리보기

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HRID 869758 반응식
FC(F)(F)S(O[C:7]1[CH:8]=[N:9][CH:10]=[C:11]([Cl:13])[CH:12]=1)(=O)=O.[C:16]1([CH2:22][SH:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)C(C)C)(C)C>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>[CH2:22]([S:23][C:7]1[CH:8]=[N:9][CH:10]=[C:11]([Cl:13])[CH:12]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1
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참가 물질

7

반응물 3

HCID 7509Benzyl mercaptanHCID 81531DiisopropylethylamineHCID 151858705-Chloropyridin-3-yl trifluoromethanesulfonate

생성물 1

HCID 583498243-(Benzylsulfanyl)-5-chloropyridine수율 104.6%

시약·촉매·용매 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)촉매
HCID 9811564
Bis(dibenzylideneacetone)palladium
촉매
HCID 1140Toluene용매

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온도
80 °C

실험 절차

To a solution of 5-chloropyridin-3-yl trifluoromethanesulfonate (1.73 g) in toluene (15 mL) were added phenylmethanethiol (861 mg), N,N-diisopropylethylamine (1.88 g), tris(dibenzylideneacetone)dipalladium(0) (121 mg) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (153 mg), and the mixture was stirred under an argon atmosphere at 80° C. for 3 hr. The reaction mixture was filtered through silica gel, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-hexane-ethyl acetate=19:1) to give the title compound as a yellow oil (yield 1.63 g, quantitative).

후처리

  1. filtrationThe reaction mixture was filtered through silica gel
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (eluent:hexane-hexane-ethyl acetate=19:1)

출처 및 근거

ORD 기록
ord-3c42c7153eac4198ab77dee2d8945a8e
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08969387B2

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