Potassium Carbonate → 5-Fluoro-2-(1-isobutyl-1H-indazol-5-yloxy)-benzonitrile

HRID 1715649노트

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HRID 1715649 반응식
[CH2:1]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([OH:14])=[CH:11][CH:12]=2)[CH:7]=[N:6]1)[CH:2]([CH3:4])[CH3:3].C([O-])([O-])=O.[K+].[K+].F[C:22]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:23]=1[C:24]#[N:25]>CN(C=O)C>[F:30][C:27]1[CH:28]=[CH:29][C:22]([O:14][C:10]2[CH:9]=[C:8]3[C:13](=[CH:12][CH:11]=2)[N:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[N:6]=[CH:7]3)=[C:23]([CH:26]=1)[C:24]#[N:25]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 1235582,5-DifluorobenzonitrileHCID 574187701-Isobutyl-1H-indazol-5-ol

생성물 1

HCID 574187715-Fluoro-2-(1-isobutyl-1H-indazol-5-yloxy)-benzonitrile수율 81%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
110 °C

실험 절차

To a solution of 1-isobutyl-1H-indazol-5-ol (2.33 g, 12.2 mmol) and K2CO3 (2.03 g, 14.7 mmol) in DMF (75 mL) was added 2,5-difluorobenzonitrile (1.87 g. 13.5 mmol). The mixture was heated to 110° C. for 18 hours under N2 atmosphere. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in dichloromethane. The solution was washed with 1N HCl, filtered, and concentrated under reduced pressure. The residue was chromatographed on Biotage eluting with hexanes/ether (5:2) to afford 3.05 g of pale yellow oil (81% yield).

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washThe solution was washed with 1N HCl
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was chromatographed on Biotage
  7. washeluting with hexanes/ether (5:2)

출처 및 근거

ORD 기록
ord-11b31424e30a4d389cce1fcff6ed6598
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07799782B2

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