Tributylvinyltin → 2-(6-chloro-3-vinylpyridin-2-yl)-4-fluoro-1H-indole

HRID 595646노트

반응식

HRID 595646 반응식
FC(F)(F)S(O[C:7]1[C:8]([C:14]2[NH:15][C:16]3[C:21]([CH:22]=2)=[C:20]([F:23])[CH:19]=[CH:18][CH:17]=3)=[N:9][C:10]([Cl:13])=[CH:11][CH:12]=1)(=O)=O.[CH2:26]([Sn](CCCC)(CCCC)C=C)[CH2:27]CC.[Li+].[Cl-]>CN(C=O)C.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>[Cl:13][C:10]1[N:9]=[C:8]([C:14]2[NH:15][C:16]3[C:21]([CH:22]=2)=[C:20]([F:23])[CH:19]=[CH:18][CH:17]=3)[C:7]([CH:26]=[CH2:27])=[CH:12][CH:11]=1

참가 물질

6

반응물 3

HCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 903335466-chloro-2-(4-fluoro-1H-indol-2-yl)pyridin-3-yl trifluoromethanesulfonate

생성물 1

HCID 903334982-(6-chloro-3-vinylpyridin-2-yl)-4-fluoro-1H-indole수율 69.8%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

To a mixture of 6-chloro-2-(4-fluoro-1H-indol-2-yl)pyridin-3-yl trifluoromethanesulfonate (2.50 g, 6.3 mmol), tributyl(vinyl)stannane (2.41 g, 7.6 mmol) and anhydrous LiCl (805 mg, 19.0 mmol) in DMF (50 mL), Pd(PPh3)2Cl2 (222 mg, 0.3 mmol) was added under N2 protection. The reaction mixture was stirred at 60° C. for 1 h. Then it was concentrated in vacuo, the residue was purified by column chromatography (PE:EA=400:1-100:1) to give the product of 2-(6-chloro-3-vinylpyridin-2-yl)-4-fluoro-1H-indole (1.20 g, yield: 69%). 1H-NMR (CDCl3, 400 MHz) δ 9.63 (br s, 1H), 7.75 (d, J=8.4 Hz, 1H), 7.28˜7.11 (m, 4H), 7.04 (s, 1H), 6.84˜6.72 (m, 1H), 5.77 (d, J=17.2 Hz, 1H), 5.60 (d, J=11.2 Hz, 1H). MS (M+H)+: 273.

후처리

  1. additionwas added under N2 protection
  2. concentrationThen it was concentrated in vacuo
  3. customthe residue was purified by column chromatography (PE:EA=400:1-100:1)

출처 및 근거

ORD 기록
ord-779f1214fbe046c1ad504f48739bcb5c
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09243002B2

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