Hydrochloric Acid → 4-((5-Chloro-6-isopropoxypyridin-3-yl)methoxy)-2,5-difluorobenzoic acid

HRID 1525662노트

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HRID 1525662 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][O:10][C:11]2[C:19]([F:20])=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[C:13]([F:21])[CH:12]=2)[CH:5]=[N:6][C:7]=1Cl.[H-].[Na+].[CH3:24][CH:25]([OH:27])[CH3:26].Cl>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][O:10][C:11]2[C:19]([F:20])=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[C:13]([F:21])[CH:12]=2)[CH:5]=[N:6][C:7]=1[O:27][CH:25]([CH3:26])[CH3:24]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 24758Sodium hydrideHCID 866825694-((5,6-Dichloropyridin-3-yl)methoxy)-2,5-difluorobenzoic acid

생성물 1

HCID 666679654-((5-Chloro-6-isopropoxypyridin-3-yl)methoxy)-2,5-difluorobenzoic acid수율 46%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
90 °C

실험 절차

To a 4-((5,6-dichloropyridin-3-yl)methoxy)-2,5-difluorobenzoic acid (Preparation 8, 210 mg, 0.63 mmol) in THF (5 mL) was added at room temperature sodium hydride (157 mg, 6.3 mmol) followed by iPrOH (5 ml). The reaction mixture was stirred at 90° C. for 18 hours. After cooling, HCl 1M (30 mL) was added to the reaction mixture and it was extracted with ethyl acetate (2×100 mL). The combined organic layers were concentrated in vacuo and purified by reverse phase chromatography to give the title compound (105 mg, 46%).

후처리

  1. temperatureAfter cooling
  2. extractionwas extracted with ethyl acetate (2×100 mL)
  3. concentrationThe combined organic layers were concentrated in vacuo
  4. custompurified by reverse phase chromatography

출처 및 근거

ORD 기록
ord-9cda74208d2a40a6a18adccdb388d253
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09085517B2

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