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

HRID 587243노트

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HRID 587243 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

반응 조건

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-befa0fd5344d4c2a93055369efc6010a
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09226500B2

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