Borane;tetrahydrofuran → Methyl 2-(5-fluoro-2-(methyloxy)-4-pyridinyl)-5-(hydroxymethyl)benzoate

HRID 404332ノート

反応式

HRID 404332 の反応式
[F:1][C:2]1[C:3]([C:10]2[CH:18]=[CH:17][C:13]([C:14](O)=[O:15])=[CH:12][C:11]=2[C:19]([O:21][CH3:22])=[O:20])=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.B.C1COCC1>C1COCC1>[F:1][C:2]1[C:3]([C:10]2[CH:18]=[CH:17][C:13]([CH2:14][OH:15])=[CH:12][C:11]=2[C:19]([O:21][CH3:22])=[O:20])=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1

参加物

4

反応物 2

HCID 2723981Borane;tetrahydrofuranHCID 574675964-(5-Fluoro-2-(methyloxy)-4-pyridinyl)-3-((methyloxy)carbonyl)benzoic acid

生成物 1

HCID 57467597Methyl 2-(5-fluoro-2-(methyloxy)-4-pyridinyl)-5-(hydroxymethyl)benzoate収率 105.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
23 °C

実験手順

To a stirred solution of 4-(5-fluoro-2-methoxypyridin-4-yl)-3-(methoxycarbonyl)benzoic acid T6.2 (0.416 g, 1 mmol) in THF (14 mL) at 0° C. was added borane-THF (3 mL, 3 mmol, 1.0M). The reaction was warmed to 23° C. and stirred for 46 hours. The reaction was then concentrated in vacuo, diluted with 1N HCl and extracted three times with EtOAc. The organic layers were combined, dried over anhydrous MgSO4, and filtered. The organic solvent was removed under reduced pressure, and the product was purified on silica gel (0-40% EtOAc in hexanes) to yield T6.3 as a colorless solid (0.307 g, 77% yield).

後処理

  1. concentrationThe reaction was then concentrated in vacuo
  2. additiondiluted with 1N HCl
  3. extractionextracted three times with EtOAc
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customThe organic solvent was removed under reduced pressure
  7. customthe product was purified on silica gel (0-40% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-43b1815264244558b16c492246cc8fe9
出典データセット
uspto-grants-2014_06
特許番号
US08748462B2

反応ノート

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