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Triphenylphosphine → 6-Vinyl-8-(3-nitrophenyl)-1,7-naphthyridine

HRID 369030
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인쇄 미리보기

반응식

HRID 369030 반응식
FC(F)(F)S(O[C:7]1[CH:8]=[C:9]2[C:14](=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=3)[N:16]=1)[N:13]=[CH:12][CH:11]=[CH:10]2)(=O)=O.[CH:28]([Sn](CCCC)(CCCC)CCCC)=[CH2:29].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl-].[Li+]>O1CCCC1.C(OCC)(=O)C.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]>[CH:28]([C:7]1[CH:8]=[C:9]2[C:14](=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=3)[N:16]=1)[N:13]=[CH:12][CH:11]=[CH:10]2)=[CH2:29]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 11776TriphenylphosphineHCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 108109346-Trifluoromethylsulfonyloxy-8-(3-nitrophenyl)-1,7-naphthyridine

생성물 1

HCID 232846366-Vinyl-8-(3-nitrophenyl)-1,7-naphthyridine

시약·촉매·용매 3

HCID 6505921
(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium
촉매
HCID 8028Tetrahydrofuran용매
HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 6-trifluoromethylsulfonyloxy-8-(3-nitrophenyl)-1,7-naphthyridine (250 mg, 0.62 mmol prepared according to example 13) in tetrahydrofuran (3 ml) is added vinyltributylstannane (218 mg, 0.68 mmol), bis(dibenzylideneacetone)palladium (14 mg, 0.025 mmol), triphenylphosphine (13 mg, 0.049 mmol) and lithium chloride (78 mg, 1.86 mmol). The mixture is kept at 70° C. overnight. The solution is diluted with ethyl acetate, filtered and washed with water. Preparative thin layer chromatography (8:2 dichloromethane/n-hexane) affords the title compound. Mass M+H 278; mp 145-151° C.

후처리

  1. filtrationfiltered
  2. washwashed with water

출처 및 근거

ORD 기록
ord-26bd93baa1d74ba2ada9eb9a7333e5c1
출처 데이터셋
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06136821

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