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

HRID 595680노트

반응식

HRID 595680 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0c1ad13d887f4096bedf64f33a50021d
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09243002B2

반응 노트

불러오는 중…