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

HRID 520672ノート

反応式

HRID 520672 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-22856af2919440daad49437f93317de0
出典データセット
uspto-grants-2016_05
特許番号
US09326975B2

反応ノート

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