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

HRID 63380

반응식

HRID 63380 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 18180031Water 1,2-dimethoxyethane용매

반응 조건

온도
120 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-0ca8794b5619488e887182cf5776361d
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447083B2

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