Ethyl Acetate → 2-(5-bromo-2-vinylpyridin-3-yl)-4-fluoro-1H-indole

HRID 595680ノート

反応式

HRID 595680 の反応式
FC(F)(F)S(O[C:7]1[C:12]([C:13]2[NH:14][C:15]3[C:20]([CH:21]=2)=[C:19]([F:22])[CH:18]=[CH:17][CH:16]=3)=[CH:11][C:10]([Br:23])=[CH:9][N:8]=1)(=O)=O.[CH2:26]([Sn](CCCC)(CCCC)C=C)[CH2:27]CC.[Li+].[Cl-].CC(=O)OCC>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>[Br:23][C:10]1[CH:11]=[C:12]([C:13]2[NH:14][C:15]3[C:20]([CH:21]=2)=[C:19]([F:22])[CH:18]=[CH:17][CH:16]=3)[C:7]([CH:26]=[CH2:27])=[N:8][CH:9]=1

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 903338395-bromo-3-(4-fluoro-1H-indol-2-yl)pyridin-2-yl trifluoromethanesulfonate

生成物 1

HCID 903335732-(5-bromo-2-vinylpyridin-3-yl)-4-fluoro-1H-indole収率 79.3%

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

A mixture of 5-bromo-3-(4-fluoro-1H-indol-2-yl)pyridin-2-yl trifluoromethanesulfonate (700 mg, 1.59 mmol), tributyl(vinyl)stannane (556 mg, 1.75 mmol), LiCl (202 mg, 4.78 mmol) and Pd(PPh3)2Cl2 (100 mg) in DMF (20 mL) was stirred at 60° C. for 3 hours under nitrogen atmosphere. The mixture was filtered through celite and concentrated in vacuo to remove DMF, and then the residue was suspended in water/EA. After extracted with EA, the combined organic phase was washed with brine, dried over sodium sulfate and concentrated to afford 2-(5-bromo-2-vinylpyridin-3-yl)-4-fluoro-1H-indole (400 mg, yield: 79%) through the column chromatography (PE:EA=20:1). 1H-NMR (CDCl3, 400 MHz) δ 8.64 (s, 1H), 8.46 (s, 1H), 7.93 (s, 1H), 7.14˜7.22 (m, 2H), 7.00˜7.07 (m, 1H), 6.82˜6.86 (m, 1H), 6.76 (s, 1H), 6.43˜6.47 (m, 1H), 5.54˜5.58 (m, 1H). MS (M+H)+: 317/319.

後処理

  1. filtrationThe mixture was filtered through celite and
  2. concentrationconcentrated in vacuo
  3. customto remove DMF
  4. extractionAfter extracted with EA
  5. washthe combined organic phase was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-0c1ad13d887f4096bedf64f33a50021d
出典データセット
uspto-grants-2016_01
特許番号
US09243002B2

反応ノート

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