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

HRID 595646ノート

反応式

HRID 595646 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-779f1214fbe046c1ad504f48739bcb5c
出典データセット
uspto-grants-2016_01
特許番号
US09243002B2

反応ノート

読み込み中…