Potassium Carbonate → N-(2-chloro-4-vinylbenzyl)pyridin-2-amine

HRID 587714노트

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HRID 587714 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH2:10][NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)[CH:5]=O.[C:18]([O-])([O-])=O.[K+].[K+]>O1CCOCC1.[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH2:18])[CH:7]=[CH:8][C:9]=1[CH2:10][NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1

참가 물질

5

반응물 2

HCID 11430Potassium CarbonateHCID 866751823-Chloro-4-((pyridin-2-ylamino)methyl)benzaldehyde

생성물 1

HCID 86675183N-(2-chloro-4-vinylbenzyl)pyridin-2-amine수율 50.4%

시약·촉매·용매 2

HCID 74505Methyltriphenyliphosphonium bromide촉매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

To a stirred solution of 3-chloro-4-((pyridin-2-ylamino)methyl)benzaldehyde (1 g, 4. mmol) in 1,4-dioxane (20 mL) were added K2CO3 (0.84 g, 6.09 mmol) and methyl triphenyl phosphonium bromide (2.17 g, 6.09 mmol) at ambient temperature. Then the resultant reaction mixture was heated at 100° C. for 18 h. After the reaction was deemed complete by TLC, the reaction mixture was cooled to ambient temperature and filtered, and the obtained filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography (SiO2, 100-200 mesh; 10% EtOAc in n-Hexane) to afford the title compound as a white solid (0.5 g, 50%): mp 119-121° C.; 1H NMR (400 MHz, CDCl3) δ 8.12 (s, 1H), 7.42-7.40 (m, 3H), 7.26 (s, 1H), 6.66 (m, 2H), 6.36 (d, J=6.3 Hz, 1H), 5.75 (d, J=13.2 Hz, 1H), 4.92 (br s, 1H), 4.60 (s, 2H); ESIMS m/z 245.05 ([M+H]+).

후처리

  1. customThen the resultant reaction mixture
  2. temperaturethe reaction mixture was cooled to ambient temperature
  3. filtrationfiltered
  4. concentrationthe obtained filtrate was concentrated under reduced pressure
  5. customThe residue was purified by flash chromatography (SiO2, 100-200 mesh; 10% EtOAc in n-Hexane)

출처 및 근거

ORD 기록
ord-432bb3034ab14b38be9644946d77f563
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09226501B2

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