Sodium Carbonate → 4-(2-(Trifluoromethoxy)phenyl)pyridine

HRID 505123노트

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HRID 505123 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][C:9]([F:12])([F:11])[F:10].B(O)(O)[C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1.C([O-])([O-])=O.[Na+].[Na+].C(Cl)Cl.CO>COCCOC.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>[F:10][C:9]([F:12])([F:11])[O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 27772661-Bromo-2-(trifluoromethoxy)benzeneHCID 21226129Dichloromethane methanol

생성물 1

HCID 463171664-(2-(Trifluoromethoxy)phenyl)pyridine수율 51%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

To a solution of (commercially available) (1-bromo-2-trifluoromethoxy-benzene) in DME (first degased with argon) under argon was added 3 mol % Pd(PPh3)4, pyridyl-4-boronic acid and 2N Na2CO3, the resulting reaction mixture was vigorously stirred under reflux. After 5 h at reflux, reaction as monitored by TLC showed completion. Two phases were separated, evaporation of most of the DME, redissolution of the residue in EtOAc and washing with aq. NaOH followed by evaporation gave a yellow oil. Flash Chromatography on SiO2 gel with a mixture of CH2Cl2/MeOH gave the title compound in 51% yield.

후처리

  1. customthe resulting reaction mixture
  2. temperatureunder reflux
  3. temperatureAfter 5 h at reflux
  4. customreaction
  5. customTwo phases were separated
  6. customevaporation of most of the DME, redissolution of the residue in EtOAc
  7. washwashing with aq. NaOH
  8. customfollowed by evaporation
  9. customgave a yellow oil

출처 및 근거

ORD 기록
ord-4781d7a064604a9088250c56dbbcb926
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07781436B2

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