Potassium Phosphate, Tribasic → N-(3'-Benzyloxy-2-bromo-5-cyano-3-methoxy-6-methylbiphenyl-4-yl)-2,2-dimethylpropionamide

HRID 17273

Reaktionsgleichung

Reaktionsgleichung von HRID 17273
[Br:1][C:2]1[C:3]([O:19][CH3:20])=[C:4]([NH:12][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])[C:5]([C:10]#[N:11])=[C:6]([CH3:9])[C:7]=1I.[CH2:21]([O:28][C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[CH:33][CH:34]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C(OCC)(=O)C.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>[CH2:21]([O:28][C:29]1[CH:34]=[C:33]([C:7]2[C:6]([CH3:9])=[C:5]([C:10]#[N:11])[C:4]([NH:12][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])=[C:3]([O:19][CH3:20])[C:2]=2[Br:1])[CH:32]=[CH:31][CH:30]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

6

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 27343133-Benzyloxy-phenylboronic acidHCID 86630795N-(3-Bromo-6-cyano-4-iodo-2-methoxy-5-methylphenyl)-2,2-dimethylpropionamide

Produkt 1

HCID 86630800N-(3'-Benzyloxy-2-bromo-5-cyano-3-methoxy-6-methylbiphenyl-4-yl)-2,2-dimethylpropionamideAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

N-(3-Bromo-6-cyano-4-iodo-2-methoxy-5-methylphenyl)-2,2-dimethylpropionamide (I-6) (1.02 g, 2.26 mmol), 3-benzyloxybenzeneboronic acid (541 mg, 2.37 mmol), tripotassium phosphate (74-85%, 1.30 g, 4.52 mmol) and tetrakis(triphenylphosphine)palladium(0) (261 mg, 0.226 mmol) were added to a 50-ml eggplant-type flask, followed by purging with nitrogen. N,N-Dimethylformamide (20 ml) was injected into it with a syringe, followed by stirring at 95° C. for 4 hours. After cooling, the reaction liquid was diluted with ethyl acetate, successively washed with saturated brine (×3), 1 N hydrochloric acid, saturated brine, an aqueous saturated sodium hydrogencarbonate solution and saturated brine, dried on anhydrous magnesium sulfate, then the solvent was concentrated under reduced pressure to obtain a pale brown residue. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=6:1) to obtain the entitled compound (630 mg, 55%) as a pale brown solid.

Aufarbeitung

  1. customby purging with nitrogen
  2. customN,N-Dimethylformamide (20 ml) was injected into it with a syringe
  3. temperatureAfter cooling
  4. customthe reaction liquid
  5. washsuccessively washed with saturated brine (×3), 1 N hydrochloric acid, saturated brine
  6. dry with materialan aqueous saturated sodium hydrogencarbonate solution and saturated brine, dried on anhydrous magnesium sulfate
  7. concentrationthe solvent was concentrated under reduced pressure
  8. customto obtain a pale brown residue
  9. customThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=6:1)

Quellen und Nachweise

ORD-Eintrag
ord-a5b661dec47f4f8c9684c3c29373a3a7
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737166B2

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