2,4-Dichloropyridine → 4-(2-Chloropyridin-4-yloxy)-2-fluorobenzenamine

HRID 450411

反応式

HRID 450411 の反応式
[F:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[NH2:8].CC(C)([O-])C.[K+].[Cl:16][C:17]1[CH:22]=[C:21](Cl)[CH:20]=[CH:19][N:18]=1>CC(N(C)C)=O>[Cl:16][C:17]1[CH:22]=[C:21]([O:9][C:4]2[CH:5]=[CH:6][C:7]([NH2:8])=[C:2]([F:1])[CH:3]=2)[CH:20]=[CH:19][N:18]=1

参加物

5

反応物 3

HCID 335152,4-DichloropyridineHCID 27359194-Amino-3-fluorophenolHCID 23665647Potassium tert-butoxide

生成物 1

HCID 594583014-(2-Chloropyridin-4-yloxy)-2-fluorobenzenamine収率 86%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

反応条件

温度
80 °C

実験手順

A suspension of 3-fluoro-4-aminophenol (8.0 g, 63.0 mmol) in dimethylacetamide (80 mL) was de-gassed in vacuo and treated with potassium tert-butoxide (7.3 g, 65 mmol). The resultant mixture was stirred at RT for 30 min. 2,4-Dichloropyridine (8 g, 54 mmol) was added and the mixture was heated to 80° C. for 12 h. The solvent was removed under reduced pressure to give a residue which was partitioned between water and EtOAc (3×100 mL). The organic layers were washed with saturated brine, dried (MgSO4), concentrated in vacuo and purified by silica gel column chromatography to give 4-(2-chloropyridin-4-yloxy)-2-fluorobenzenamine (11 g, 86% yield). 1H NMR (300 MHz, DMSO-d6): δ 8.24 (d, J=5.7 Hz, 1H), 7.00 (dd, J=9.0, 2.7 Hz, 1H), 6.89-6.73 (m, 4H), 5.21 (br s, 2H); MS (ESI) m/z: 239.2 (M+H+).

後処理

  1. customwas de-gassed in vacuo
  2. customThe solvent was removed under reduced pressure
  3. customto give a residue which
  4. customwas partitioned between water and EtOAc (3×100 mL)
  5. washThe organic layers were washed with saturated brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. custompurified by silica gel column chromatography

出典と根拠

ORDレコード
ord-ac21ac849c3c4e0ba2313873b62a0821
出典データセット
uspto-grants-2013_07
特許番号
US08486951B2

関連ノート

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