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

HRID 587714ノート

反応式

HRID 587714 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 74505Methyltriphenyliphosphonium bromide触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

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]+).

後処理

  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)

出典と根拠

ORDレコード
ord-432bb3034ab14b38be9644946d77f563
出典データセット
uspto-grants-2016_01
特許番号
US09226501B2

反応ノート

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