Sodium Carbonate → tert-butyl 2-(4-amino-2-propyl-2H-pyrazolo[3,4-c]quinolin-1-yl)ethylcarbamate

HRID 2283799

Reaktionsgleichung

Reaktionsgleichung von HRID 2283799
Br[C:2]1[C:3]([C:20]#[N:21])=[N:4][N:5]([CH2:17][CH2:18][CH3:19])[C:6]=1[CH2:7][CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13].Cl.[NH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1B(O)O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C(O)CC>[NH2:21][C:20]1[C:3]2=[N:4][N:5]([CH2:17][CH2:18][CH3:19])[C:6]([CH2:7][CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[C:2]2[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[N:23]=1

Komponenten

8

Edukt 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 164270902-Aminophenylboronic acid hydrochlorideHCID 66958960tert-butyl 2-(4-bromo-3-cyano-1-propyl-1H-pyrazol-5-yl)ethylcarbamate

Produkt 1

HCID 66958848tert-butyl 2-(4-amino-2-propyl-2H-pyrazolo[3,4-c]quinolin-1-yl)ethylcarbamateAusbeute 44,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittel2×HCID 10311-PropanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A flask containing a mixture of tert-butyl 2-(4-bromo-3-cyano-1-propyl-1H-pyrazol-5-yl)ethylcarbamate (15.8 g, 44.2 mmol), 2-aminophenylboronic acid hydrochloride (11.5 g, 66.3 mmol), triphenylphosphine (1.04 g, 3.98 mmol), palladium (II) acetate (299 mg, 1.33 mmol), 2 M aqueous sodium carbonate (67 mL, 133 mmol), 1-propanol (77.4 mL), and water (15.5 mL) was heated overnight under a nitrogen atmosphere in a 100° C. oil bath. The reaction was allowed to cool to ambient temperature and water (300 mL) was added. The mixture was extracted with chloroform, dried over magnesium sulfate, filtered, and concentrated to provide an oil that was purified twice by flash chromatography (silica gel, first column: eluted sequentially with 0-10% CMA in chloroform, and then 25% CMA in chloroform; second column: gradient elution with 50-60% ethyl acetate in hexanes) to yield 7.3 g of tert-butyl 2-(4-amino-2-propyl-2H-pyrazolo[3,4-c]quinolin-1-yl)ethylcarbamate as a yellow resin.

Aufarbeitung

  1. additionA flask containing
  2. temperatureto cool to ambient temperature
  3. extractionThe mixture was extracted with chloroform
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto provide an oil that
  8. customwas purified twice by flash chromatography (silica gel, first column
  9. washeluted sequentially with 0-10% CMA in chloroform
  10. washsecond column: gradient elution with 50-60% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-f0ed726626ff42de95b5bf1368f8c871
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09145410B2

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