Cesium fluoride → HCID 70979015、化合物

HRID 2361609ノート

反応式

HRID 2361609 の反応式
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[C:5]([O:14][CH3:15])=[CH:4][N:3]=1.[F-:16].[Cs+]>CS(C)=O.O>[F:16][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[C:5]([O:14][CH3:15])=[CH:4][N:3]=1

参加物

5

反応物 2

HCID 25953Cesium fluorideHCID 22250112HCID 22250112、化合物

生成物 1

HCID 70979015HCID 70979015、化合物収率 20.15%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
145 °C

実験手順

To a solution of 1-chloro-4,6-dimethoxyisoquinoline (1.5 g, 6.71 mmol) in DMSO (15 ml) was added cesium fluoride (4 g, 26.8 mmol) at room temperature. The reaction vessel (Pressure tube) was sealed and heated at 145° C. for 18 h. The reaction mass was diluted with water and extracted with ethyl acetate. The combined organic layer was dried over anhydrous Na2SO4 and evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography to get desired compound (280 mg, 20.15%) as white solid. 1H NMR (400 MHz, CDCl3): δ ppm 7.99-7.97 (d, J=8 Hz, 1H), 7.44-7.39 (m, 2H), 7.27-7.11 (m, 1H), 4.03 (s, 3H), 3.97 (s, 3H); 19F NMR: δ ppm −79.32 (1 F); MS: MS m/z 208.0 (M++1).

後処理

  1. customThe reaction vessel (Pressure tube) was sealed
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  4. customevaporated under reduced pressure
  5. customto get crude compound
  6. customThe crude compound was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-e8d99479ffeb4eb6b7bd0234ca5ca523
出典データセット
uspto-grants-2014_04
特許番号
US08691757B2

反応ノート

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