Toluene → 6-methyl-3'-nitro-N-[3-(trifluoromethyl)phenyl]biphenyl-3-carboxamide

HRID 77724

반응식

HRID 77724 반응식
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)O1.I[C:20]1[CH:21]=[C:22]([CH:36]=[CH:37][C:38]=1[CH3:39])[C:23]([NH:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=1)=[O:24].C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>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.O.C(O)C>[CH3:39][C:38]1[C:20]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)=[CH:21][C:22]([C:23]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:33])([F:34])[F:35])[CH:27]=2)=[O:24])=[CH:36][CH:37]=1

참가 물질

8

반응물 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 112651643-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzeneHCID 171975693-iodo-4-methyl-N-(3-(trifluoromethyl)phenyl)benzamide

생성물 1

HCID 692737816-methyl-3'-nitro-N-[3-(trifluoromethyl)phenyl]biphenyl-3-carboxamide

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 962Water용매

실험 절차

4,4,5,5-Tetramethyl-2-(3-nitrophenyl)-1,3,2-dioxaborolane (1.4 g, 5.6 mmol) was mixed with 3-iodo-4-methyl-N-[3-(trifluoromethyl)phenyl]benzamide (2.00 g, 4.94 mmol), potassium carbonate (1.4 g, 9.9 mmol), toluene (40 mL), ethanol (6.0 mL), and water (4.0 mL). The mixture was degassed and tetrakis(triphenylphosphine)palladium(0) (0.27 g, 0.24 mmol) was added. The resulting mixture was heated to reflux for 16 hours. The reaction was then cooled and was extracted with ethyl acetate. The organic extracts were washed with water, brine, dried (Na2SO4) and concentrated. The product was purified by flash column chromatography, eluting with a gradient of 20-50% ethyl acetate in hexanes (1.92 g, 91%).

후처리

  1. customThe mixture was degassed
  2. temperatureThe resulting mixture was heated
  3. temperatureto reflux for 16 hours
  4. temperatureThe reaction was then cooled
  5. extractionwas extracted with ethyl acetate
  6. washThe organic extracts were washed with water, brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customThe product was purified by flash column chromatography
  10. washeluting with a gradient of 20-50% ethyl acetate in hexanes (1.92 g, 91%)

출처 및 근거

ORD 기록
ord-4b33ffaa42fa4924988fa781d468829c
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841318B2

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