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

HRID 1159448노트

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HRID 1159448 반응식
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

참가 물질

7

반응물 4

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

생성물 1

HCID 451233613-(4-Aminophenyl)-5-chloroisonicotinonitrile수율 35.2%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
85 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-80bc70c4e17a40dba913b4aa23bd769a
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07812166B2

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