5-Amino-2-chloro-4-fluorophenol → 5-(5-Amino-2-chloro-4-fluorophenoxy)picolinonitrile

HRID 1711623ノート

反応式

HRID 1711623 の反応式
[NH2:1][C:2]1[C:3]([F:10])=[CH:4][C:5]([Cl:9])=[C:6]([OH:8])[CH:7]=1.CC(C)([O-])C.[K+].Cl[C:18]1[CH:19]=[CH:20][C:21]([C:24]#[N:25])=[N:22][CH:23]=1>CC(N(C)C)=O.O>[NH2:1][C:2]1[C:3]([F:10])=[CH:4][C:5]([Cl:9])=[C:6]([CH:7]=1)[O:8][C:18]1[CH:19]=[CH:20][C:21]([C:24]#[N:25])=[N:22][CH:23]=1

参加物

6

反応物 3

HCID 1586545-Amino-2-chloro-4-fluorophenolHCID 38339425-Chloro-2-cyanopyridineHCID 23665647Potassium tert-butoxide

生成物 1

HCID 672540795-(5-Amino-2-chloro-4-fluorophenoxy)picolinonitrile

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 31374Dimethylacetamide溶媒

実験手順

A solution of 5-amino-2-chloro-4-fluorophenol (100 mg, 0.619 mmol) in degassed dimethylacetamide (2 mL) was treated with potassium t-butoxide (83 mg, 0.743 mmol) and 5-chloro-2-cyanopyridine (86 mg, 0.619 mmol). The resultant mixture was heated to 80° C. overnight, then cooled to RT and diluted with water (10 mL). The mixture was extracted with EtOAc (30 mL). The organic phase was washed with water (3×30 mL) and brine (30 mL) dried (Na2SO4) and concentrated in vacuo to provide 5-(5-amino-2-chloro-4-fluorophenoxy)picolinonitrile as a dark oil which was used without further purification. MS (ESI) m/z: 264.0 (M+H+).

後処理

  1. extractionThe mixture was extracted with EtOAc (30 mL)
  2. washThe organic phase was washed with water (3×30 mL) and brine (30 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-a56459ab31fe44be8ce0fa9a19f0d1a1
出典データセット
uspto-grants-2010_09
特許番号
US07790756B2

反応ノート

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