Sodium hydride → 4-(4-Amino-2,5-difluorophenoxy)pyridine-2-carboxamide

HRID 520672노트

반응식

HRID 520672 반응식
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([OH:9])=[C:4]([F:10])[CH:3]=1.Cl[C:12]1[CH:17]=[CH:16][N:15]=[C:14]([C:18]([NH2:20])=[O:19])[CH:13]=1.[H-].[Na+]>CN(C=O)C.O>[NH2:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([O:9][C:12]2[CH:17]=[CH:16][N:15]=[C:14]([C:18]([NH2:20])=[O:19])[CH:13]=2)=[C:4]([F:10])[CH:3]=1

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 3035434-Chloropyridine-2-carboxamideHCID 27787624-Amino-2,5-difluorophenol

생성물 1

HCID 247886284-(4-Amino-2,5-difluorophenoxy)pyridine-2-carboxamide수율 30.6%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a mixture of 4-amino-2,5-difluorophenol (100 mg, 0.64 mmol), and 4-chloropicolinamide (110 mg, 0.71 mmol) in DMF (2 mL) was added NaH (80 mg, 1.3 mmol, 60% dispersed in mineral oil). The reaction mixture was microwaved at 120° C. for 1.5 hours, then cooled to rt, diluted with water (20 mL), and extracted with EtOAc (30 mL×3). The combined organic phases were washed with brine (80 mL), dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography with (EtOAc/PE (v/v)=4/1) to afford the title compound as a brown solid (52 mg, 26%).

후처리

  1. customThe reaction mixture was microwaved at 120° C. for 1.5 hours
  2. extractionextracted with EtOAc (30 mL×3)
  3. washThe combined organic phases were washed with brine (80 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography with (EtOAc/PE (v/v)=4/1)

출처 및 근거

ORD 기록
ord-22856af2919440daad49437f93317de0
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09326975B2

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