3-Nitrophenylboronic Acid → 3-Fluoro-N-(6-methyl-3'-nitrobiphenyl-3-yl)-5-(trifluoromethyl)benzamide

HRID 77701

Reaktionsgleichung

Reaktionsgleichung von HRID 77701
[N+:1]([C:4]1[CH:5]=[C:6](B(O)O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[F:13][C:14]1[CH:15]=[C:16]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1)[C:17]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[C:22](I)[CH:21]=1)=[O:18].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.O.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:13][C:14]1[CH:15]=[C:16]([CH:28]=[C:29]([C:31]([F:32])([F:33])[F:34])[CH:30]=1)[C:17]([NH:19][C:20]1[CH:25]=[C:24]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[C:23]([CH3:26])=[CH:22][CH:21]=1)=[O:18]

Komponenten

8

Edukt 3

HCID 16773-Nitrophenylboronic AcidHCID 11430Potassium CarbonateHCID 690440933-fluoro-N-(3-iodo-4-methylphenyl)-5-(trifluoromethyl)benzamide

Produkt 1

HCID 690453213-Fluoro-N-(6-methyl-3'-nitrobiphenyl-3-yl)-5-(trifluoromethyl)benzamideAusbeute 97,8 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

(3-Nitrophenyl)boronic acid (1.7 g, 10.0 mmol) was mixed with 3-fluoro-N-(3-iodo-4-methylphenyl)-5-(trifluoromethyl)benzamide (4.30 g, 10.2 mmol) and potassium carbonate (2.5 g, 18 mmol) in toluene (75.00 mL), ethanol (11.00 mL) and water (10.00 mL) and was degassed. To the mixture was added tetrakis(triphenylphosphine)palladium(0) (0.50 g, 0.43 mmol) and the resulting mixture was heated to reflux for 18 hours. The reaction was extracted with ethyl acetate and the organic extracts were washed with water, saturated NaCl, dried (MgSO4) and then concentrated in vacuo. The residue was purified by column chromatography using 20% EtOAc/hexanes to give the product (4.09 g, 96% yield). MS (EI) m/z=419 (M+H).

Aufarbeitung

  1. customwas degassed
  2. temperaturethe resulting mixture was heated
  3. temperatureto reflux for 18 hours
  4. extractionThe reaction was extracted with ethyl acetate
  5. washthe organic extracts were washed with water, saturated NaCl
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-442af3d882b14a718fe0e589c8f5dd08
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841318B2

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