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

HRID 715403노트

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HRID 715403 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
90 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-75bfb6aa46234c3a86a928f62177c602
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187475B2

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