Dichloromethane → 3-(4-Aminophenyl)-5-chloroisonicotinonitrile

HRID 1159448ノート

反応式

HRID 1159448 の反応式
Cl[C:2]1[CH:9]=[N:8][CH:7]=[C:6]([Cl:10])[C:3]=1[C:4]#[N:5].CC1(C)C(C)(C)OB([C:19]2[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=2)O1.C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.O>[NH2:25][C:22]1[CH:23]=[CH:24][C:19]([C:2]2[CH:9]=[N:8][CH:7]=[C:6]([Cl:10])[C:3]=2[C:4]#[N:5])=[CH:20][CH:21]=1

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 111375993,5-Dichloropyridine-4-carbonitrile

生成物 1

HCID 451233613-(4-Aminophenyl)-5-chloroisonicotinonitrile収率 35.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
85 °C

実験手順

The product from Example 1B (3 g, 17.3 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (4.18 g, 19 mmol), PdCl2dppf.CH2Cl2 (300 mg), and Na2CO3 (4.5 g) were combined in DMF (25 mL) and water (10 mL). The mixture was degassed with nitrogen and heated to 85° C. overnight The mixture was allowed to cool to room temperature and partitioned between water and ethyl acetate. The organic layer was dried (Na2SO4), filtered, and the filtrate was concentrated under reduced pressure. The residue was purified via silica gel chromatography eluting with hexanes:ethyl acetate (1:1) to provide 1.4 g of the title compound. 1H NMR (300 MHz, DMSO-D6) δ ppm 5.67 (s, 2H) 6.70 (d, J=8.48 Hz, 2H) 7.40 (d, J=8.82 Hz, 2H) 8.76 (s, 1H) 8.79 (s, 1H).

後処理

  1. customThe mixture was degassed with nitrogen
  2. temperatureto cool to room temperature
  3. custompartitioned between water and ethyl acetate
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified via silica gel chromatography
  8. washeluting with hexanes:ethyl acetate (1:1)

出典と根拠

ORDレコード
ord-80bc70c4e17a40dba913b4aa23bd769a
出典データセット
uspto-grants-2010_10
特許番号
US07812166B2

反応ノート

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