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

HRID 1525662ノート

反応式

HRID 1525662 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
90 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-9cda74208d2a40a6a18adccdb388d253
出典データセット
uspto-grants-2015_07
特許番号
US09085517B2

反応ノート

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