Sodium Carbonate → 3-(2-Thienyl)pyridine

HRID 2771

반응식

HRID 2771 반응식
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[S:8]1[CH:12]=[CH:11][CH:10]=[C:9]1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC>[S:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 122863-BromopyridineHCID 27339602-Thiopheneboronic acid

생성물 1

HCID 5951453-(2-Thienyl)pyridine수율 16.3%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

실험 절차

A mixture of 3-bromopyridine (1.30 mL, 13.5 mmol) and tetrakis(triphenylphosphine) (0.468 g, 0.41 mmol) in 40 mL of dimethoxyethane is stirred under nitrogen at room temperature for 10 min. 2-Thiophene boronic acid (1.90 g, 14.8 mmol) and 20 mL of 1N sodium carbonate are added and the resulting mixture is refluxed overnight. The solution is cooled to room temperature and filtered through Celite. The filtrated is extracted with ether (2×30 mL). The combined organic layers are dried over MgSO4, filtered and concentrated. The crude product is purified by column chromatography eluting with a gradient of 10% EtOAc/hexanes to 20% EtOAc/hexanes to afford the title compound (0.355 g, 2.20 mmol) as a light yellow oil.

후처리

  1. temperaturethe resulting mixture is refluxed overnight
  2. temperatureThe solution is cooled to room temperature
  3. filtrationfiltered through Celite
  4. extractionThe filtrated is extracted with ether (2×30 mL)
  5. dry with materialThe combined organic layers are dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product is purified by column chromatography
  9. washeluting with a gradient of 10% EtOAc/hexanes to 20% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-8d5d986597254a4b95b496e32a884a31
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05731315

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