Toluene → 2-((3-Chloro-5-vinylpyridin-2-yl)methyl)isoindoline-1,3-dione

HRID 587247노트

반응식

HRID 587247 반응식
Br[C:2]1[CH:3]=[C:4]([Cl:20])[C:5]([CH2:8][N:9]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]2=[O:19])=[N:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].[C:27]1(C)C=CC=C[CH:28]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:20][C:4]1[C:5]([CH2:8][N:9]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]2=[O:19])=[N:6][CH:7]=[C:2]([CH:27]=[CH2:28])[CH:3]=1

참가 물질

5

반응물 3

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 711385752-((5-Bromo-3-chloropyridin-2-yl)methyl)isoindoline-1,3-dione

생성물 1

HCID 866751842-((3-Chloro-5-vinylpyridin-2-yl)methyl)isoindoline-1,3-dione수율 65%

시약·촉매·용매 1

HCID 178418397HCID 178418397, 화합물촉매

실험 절차

To a stirred solution of 2-((5-bromo-3-chloropyridin-2-yl)methyl)isoindoline-1,3-dione (0.23 g, 0.65 mmol) in toluene (10 mL) were added Pd(PPh3)4 (3.7 mg, 0.003 mmol), K2CO3 (0.269 g, 1.95 mmol) and vinyl boronic anhydride pyridine complex (0.78 g, 3.28 mmol), and the reaction mixture was heated at reflux for 16 h. The reaction mixture was filtered, and the filtrate was washed with water and brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure. Purification by flash column chromatography (20-30% EtOAc in hexane) afforded the title compound as an off-white solid (0.2 g, 65%): 1H NMR (400 MHz, CDCl3) δ 8.30 (s, 1H), 7.91 (m, 2H), 7.77 (m, 3H), 7.72 (m, 1H), 6.63 (m, 1H), 5.79 (d, J=16.0 Hz, 1H), 5.39 (d, J=16.0 Hz, 1H), 5.12 (s, 2H); ESIMS m/z 299.20 ([M+H]+).

후처리

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 16 h
  3. filtrationThe reaction mixture was filtered
  4. washthe filtrate was washed with water and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash column chromatography (20-30% EtOAc in hexane)

출처 및 근거

ORD 기록
ord-6e143a3690e440dfbc987da40e9b61b4
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09226500B2

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