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

HRID 1502724노트

반응식

HRID 1502724 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 H2O 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 H2O 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-2c21f8ff584a473c993e7050b1fcea69
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09210927B2

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