2,4-Dichloropyridine → 4-(2-Chloro-pyridin-4-yloxy)-2-fluoro-3-methyl-phenylamine

HRID 2042070ノート

反応式

HRID 2042070 の反応式
CC(C)([O-])C.[K+].[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([CH3:15])[C:9]=1[F:16].[Cl:17][C:18]1[CH:23]=[C:22](Cl)[CH:21]=[CH:20][N:19]=1>CC(N(C)C)=O>[Cl:17][C:18]1[CH:23]=[C:22]([O:14][C:11]2[CH:12]=[CH:13][C:8]([NH2:7])=[C:9]([F:16])[C:10]=2[CH3:15])[CH:21]=[CH:20][N:19]=1

参加物

5

反応物 3

HCID 335152,4-DichloropyridineHCID 23665647Potassium tert-butoxideHCID 552890104-Amino-3-fluoro-2-methylphenol

生成物 1

HCID 866196704-(2-Chloro-pyridin-4-yloxy)-2-fluoro-3-methyl-phenylamine収率 42.2%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒2 回

反応条件

温度
100 °C

実験手順

Potassium tert-butoxide (3.5 g, 0.031 mol) was added to a solution of 4-amino-3-fluoro-2-methylphenol (4.2 g, 0.03 mol) in DMAc and the resultant mixture was stirred for 30 min at RT. To this mixture was added a solution of 2,4-dichloropyridine (4.38 g, 0.03 mol) in DMAc and the mixture was heated at 100° C. overnight. The reaction mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate (200 mL) and filtered through silica gel, washing forward with EtOAc. The filtrate was concentrated and purified by silica gel chromatography to give 4-(2-chloropyridin-4-yloxy)-2-fluoro-3-methylbenzenamine (3.2 g, 42% yield). 1H NMR (300 MHz, DMSO-d6) δ 8.21 (d, J=6.0 Hz, 1H), 6.84 (s, 1H), 6.81 (dd, J=5.6, 2.4 Hz, 1H), 6.67 (m, 2H), 5.12 (s, 2H), 1.91 (s, 3H); MS (ESI) m/z 253.1 [M+H]+.

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate (200 mL)
  3. filtrationfiltered through silica gel
  4. washwashing forward with EtOAc
  5. concentrationThe filtrate was concentrated
  6. custompurified by silica gel chromatography

出典と根拠

ORDレコード
ord-a7f0882fb50644ac91b758accab8f00e
出典データセット
uspto-grants-2013_11
特許番号
US08586565B2

反応ノート

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