Sodium Carbonate → 3-Hydroxy-2-(thiophen-3-YL)pyridine

HRID 63380

反応式

HRID 63380 の反応式
Br[C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[S:9]1[CH:13]=[CH:12][C:11](B(O)O)=[CH:10]1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.O>[S:9]1[CH:13]=[CH:12][C:11]([C:2]2[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:10]1

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 230702-Bromo-3-pyridinolHCID 581760Thiophene-3-boronic acid

生成物 1

HCID 532174763-Hydroxy-2-(thiophen-3-YL)pyridine収率 48.6%

試薬・触媒・溶媒 1

HCID 18180031Water 1,2-dimethoxyethane溶媒

反応条件

温度
120 °C

実験手順

2-Bromopyridin-3-ol (100 mg, 0.58 mmol), 3-thiophenyl boronic acid (88 mg, 0.69 mmol), sodium carbonate (184 mg, 2.07 mmol) and Pd2(dppf)2Cl2 (94 mg, 0.12 mmol) were dissolved in dimethoxyethane/water of 1 mL/1 mL, followed by stirring in microwave at 120° C. for 20 minutes. After the completion of the reaction, the reaction mixture was filtered using Celite. The filtrate was added with water, and extracted with ethyl acetate. The obtained organic layer was dried over magnesium sulfate, and purified by column chromatography (ethyl acetate:hexane=1:3) to obtain 2-(thiophene-3-yl)pyridin-3-ol (50 mg, 48%).

後処理

  1. customAfter the completion of the reaction
  2. filtrationthe reaction mixture was filtered
  3. additionThe filtrate was added with water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe obtained organic layer was dried over magnesium sulfate
  6. custompurified by column chromatography (ethyl acetate:hexane=1:3)

出典と根拠

ORDレコード
ord-0ca8794b5619488e887182cf5776361d
出典データセット
uspto-grants-2016_09
特許番号
US09447083B2

関連ノート

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