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1-Propanol → HCID 66958580, Verbindung

HRID 2283772
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2283772
[CH2:1]([N:8]1[C:12]([CH3:13])=[C:11](Br)[C:10]([C:15]#[N:16])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17][C:18]([CH3:32])([CH3:31])[C:19]([NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1B(O)O)=[O:20].C(O)CC.C(=O)([O-])[O-].[Na+].[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC)(C)(C)C.O>[CH2:1]([N:8]1[C:12]([CH3:13])=[C:11]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[NH:21][C:19](=[O:20])[C:18]([CH3:31])([CH3:17])[CH3:32])[C:10]([C:15]#[N:16])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 10311-PropanolHCID 10340Sodium CarbonateHCID 41935022-(Pivalamido)phenylboronic AcidHCID 669586391-Benzyl-4-bromo-5-methyl-1H-pyrazole-3-carbonitrile

Produkt 1

HCID 66958580HCID 66958580, VerbindungAusbeute 59,1 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 11776
Triphenylphosphine
Katalysator
HCID 167845palladium(II) acetateKatalysator
HCID 962WaterLösungsmittel
HCID 15413tert-Butyl methyl etherLösungsmittel

Versuchsvorschrift

1-Benzyl-4-bromo-5-methyl-1H-pyrazole-3-carbonitrile (3.00 g, 10.9 mmol) was treated with triphenylphosphine (85 mg, 0.32 mmol), 2-[(2,2-dimethylpropanoyl)amino]phenylboronic acid (prepared as described in Part G of Example 23, 2.15 g, 16.3 mmol), 1-propanol (22 mL), palladium (II) acetate (24 mg, 0.11 mmol), aqueous sodium carbonate (6.5 mL of 2 M, 13 mmol), and water (4.4 mL) according to the general procedure described in Example 34. The reaction time was approximately 16 hours and no additional reagents were added. The reaction was allowed to cool to ambient temperature and methyl tert-butyl ether (25 mL) was added. After the mixture was stirred for about 10 minutes, the layers were separated. The organic layer was dried over magnesium sulfate, filtered, and concentrated to yield a brown oil. The crude product was purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution 1-30% ethyl acetate in hexanes). The appropriate fractions were combined, dried over magnesium sulfate, filtered, and concentrated to yield 2.40 g of N-[2-(1-benzyl-3-cyano-5-methyl-1H-pyrazol-4-yl)phenyl]-2,2-dimethylpropanamide as an oil that solidified upon standing at ambient temperature.

Aufarbeitung

  1. additionno additional reagents were added
  2. customthe layers were separated
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto yield a brown oil
  7. customThe crude product was purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution 1-30% ethyl acetate in hexanes)
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-63e9d0e84f8d4b19851fc2f1bbb86499
Quelldatensatz
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09145410B2

Notizen zur Reaktion

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