Ethanol → 3-(2-Nitro-4-(trifluoromethyl)phenyl)pyridine

HRID 502731

반응식

HRID 502731 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](B(O)O)[CH:2]=1.Br[C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:12]=1[NH2:21].C(=O)([O-])[O-:23].[Na+].[Na+].C(O)C.[OH2:31]>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.C1(C)C=CC=CC=1>[N+:21]([C:12]1[CH:13]=[C:14]([C:17]([F:20])([F:19])[F:18])[CH:15]=[CH:16][C:11]=1[C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)([O-:23])=[O:31]

참가 물질

8

반응물 5

HCID 702EthanolHCID 962WaterHCID 10340Sodium CarbonateHCID 679892-Bromo-5-(trifluoromethyl)benzenamineHCID 27343783-Pyridinylboronic acid

생성물 1

HCID 463167623-(2-Nitro-4-(trifluoromethyl)phenyl)pyridine

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

실험 절차

A mixture of pyridin-3-ylboronic acid (0.99 g, 8.1 mmol), 2-bromo-5-(trifluoromethyl)benzenamine (1.2 ml, 8.1 mmol), tetrakis(triphenylphosphine)palladium (0.28 g, 0.24 mmol), sodium carbonate (2.0 M solution in water, 8.0 ml, 16 mmol), 4 ml ethanol, and 20 ml toluene was heated to 90° C. under nitrogen with a water-cooled reflux condenser. After 12 h, mixture was cooled to ambient temperature, and was partitioned between EtOAc and 1N NaOH. The organic layer was washed once with brine, dried with Na2SO4, filtered, and concentrated to give a brown oil, which was further purified by silica gel chromatography (EtOAc/hexanes) to give the desired product as a waxy orange solid. MS (m/z): 269.0 (M+H)+. Calc'd for C12H7F3N2O2: 268.19.

후처리

  1. temperaturecooled
  2. temperaturereflux condenser
  3. customwas partitioned between EtOAc and 1N NaOH
  4. washThe organic layer was washed once with brine
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a brown oil, which
  9. customwas further purified by silica gel chromatography (EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-ab9f26e31d1e46f2ad5a813e4d78b546
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776869B2

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