Sodium Carbonate → 2-Fluoro-2'-(trifluoromethyl)-3,4'-bipyridine

HRID 473624노트

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HRID 473624 반응식
[F:1][C:2]1[C:7](B(O)O)=[CH:6][CH:5]=[CH:4][N:3]=1.Br[C:12]1[CH:17]=[CH:16][N:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(O)C.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:1][C:2]1[C:7]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

참가 물질

8

반응물 3

HCID 10340Sodium CarbonateHCID 27832702-Fluoropyridine-3-boronic acidHCID 234369504-Bromo-2-(trifluoromethyl)pyridine

생성물 1

HCID 593269242-Fluoro-2'-(trifluoromethyl)-3,4'-bipyridine

시약·촉매·용매 4

HCID 178418476HCID 178418476, 화합물촉매HCID 702Ethanol용매HCID 962Water용매2회HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
95 °C

실험 절차

A mixture of 2-fluoropyridin-3-ylboronic acid (0.748 g, 5.3 mmol), 4-bromo-2-(trifluoromethyl)pyridine (1.00 g, 4.4 mmol), Pd(PPh3)2Cl2 (0.155 g, 0.22 mmol) and sodium carbonate (0.797 g, 13.3 mmol) in DME (6.5 mL), ethanol (1.9 mL) and water (0.47 mL) was heated to 95° C. for 2 h. After cooling to room temperature, the mixture was diluted with H2O and extracted with CH2Cl2 (3×). The combined organics were dried over Na2SO4, filtered and concentrated. The residue was purified using column chromatography (EtOAc/Hexanes=0→20%) to give the title compound. MS (ESI, pos. ion) m/z: 243 (M+1).

후처리

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with CH2Cl2 (3×)
  3. dry with materialThe combined organics were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified

출처 및 근거

ORD 기록
ord-982a471bee604723b4b7c88e00e160e7
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637500B2

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