4-Fluorophenol → Methyl 6-(4-fluorophenoxy)-5-methylnicotinate

HRID 715403ノート

反応式

HRID 715403 の反応式
F[C:2]1[C:11]([CH3:12])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[F:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:2]2[C:11]([CH3:12])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=2)=[CH:16][CH:15]=1

参加物

5

反応物 3

HCID 97324-FluorophenolHCID 11430Potassium CarbonateHCID 53419770Methyl 6-fluoro-5-methylpyridine-3-carboxylate

生成物 1

HCID 89875052Methyl 6-(4-fluorophenoxy)-5-methylnicotinate収率 93.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

A mixture of methyl 6-fluoro-5-methylnicotinate (2.40 g, 14.2 mmol, Step-1 of Amine-36), 4-fluorophenol (2.39 g, 21.3 mmol), and potassium carbonate (3.92 g, 28.4 mmol) in DMF (45 mL) is stirred at 90° C. for 3 hours. After cooling to rt, the mixture is filtered through a pad of Celite and rinsed with EtOAc (200 mL). The filtrate is washed with water (200 mL) and brine (200 mL), and the organic layer is dried over sodium sulfate. After filtration, and the filtrate is concentrated in vacuo. The residue is purified by chromatography on silica gel eluting with n-hexane/EtOAc (20:1) to give 3.46 g (93% yield) of the title compound as white solid.

後処理

  1. temperatureAfter cooling to rt
  2. filtrationthe mixture is filtered through a pad of Celite
  3. washrinsed with EtOAc (200 mL)
  4. washThe filtrate is washed with water (200 mL) and brine (200 mL)
  5. dry with materialthe organic layer is dried over sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate is concentrated in vacuo
  8. customThe residue is purified by chromatography on silica gel eluting with n-hexane/EtOAc (20:1)

出典と根拠

ORDレコード
ord-75bfb6aa46234c3a86a928f62177c602
出典データセット
uspto-grants-2015_11
特許番号
US09187475B2

反応ノート

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