Sodium Carbonate → 3-Bromo-5-thiophen-3-yl-pyridine

HRID 1385993노트

반응식

HRID 1385993 반응식
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[S:9]1[CH:13]=[CH:12][C:11](B(O)O)=[CH:10]1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:8][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([C:11]2[CH:12]=[CH:13][S:9][CH:10]=2)[CH:7]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 693693,5-DibromopyridineHCID 581760Thiophene-3-boronic acid

생성물 1

HCID 112764923-Bromo-5-thiophen-3-yl-pyridine

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 312751,4-Dioxane용매

실험 절차

A deoxygenated solution of 3,5-dibromopyridine (4.00 g, 16.9 mmol, 1 equiv), 3-thiopheneboronic acid (2.38 g, 18.6 mmol, 1.10 equiv), Pd(PPh3)4 (781 mg, 0.676 mmol, 0.0433 equiv), and 2.0 M Na2CO3 (16.9 mL, 33.8 mmol, 2.00 equiv) in dioxane (40 ml) was heated under argon at reflux for 20 h. The reaction mixture was allowed to cool, then partitioned between water (200 mL) and ethyl acetate (2×300 mL). The combined organic layers were dried over sodium sulfate and concentrated. The residue was purified by flash column chromatography (5% ethyl acetate in dichloromethane) to afford 3-bromo-5-thiophen-3-yl-pyridine as a white solid.

후처리

  1. temperatureat reflux for 20 h
  2. temperatureto cool
  3. custompartitioned between water (200 mL) and ethyl acetate (2×300 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography (5% ethyl acetate in dichloromethane)

출처 및 근거

ORD 기록
ord-894d7d9f6cbf461b80a5bbec4d00673a
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06265403B1

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