Potassium Carbonate → 3-tert-butyl-4-methyl-1-(2-methylphenyl)-1H-pyrazol-5-amine

HRID 915571Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 915571
Br[C:2]1[C:3]([C:15]([CH3:18])([CH3:17])[CH3:16])=[N:4][N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH3:14])[C:6]=1[NH2:7].[CH3:19]B1OB(C)OB(C)O1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[C:15]([C:3]1[C:2]([CH3:19])=[C:6]([NH2:7])[N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH3:14])[N:4]=1)([CH3:18])([CH3:17])[CH3:16]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 589586014-bromo-3-tert-butyl-1-(2-methylphenyl)-1H-pyrazol-5-amine2×

Produkt 1

HCID 589586213-tert-butyl-4-methyl-1-(2-methylphenyl)-1H-pyrazol-5-amineAusbeute 38,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
155 °C

Versuchsvorschrift

To a solution of 4-bromo-3-tert-butyl-1-(2-methylphenyl)-1H-pyrazol-5-amine (Intermediate J, 800 mg, 2.60 mmol) in DMF (5 mL) was added trimethylboroxine (0.73 mL, 5.19 mmol), [1,1′-bis(diphenylphosphino)-butane]palladium (II) dichloride (157 mg, 0.26 mmol), and potassium carbonate (1.08 g, 7.79 mmol). The reaction mixture was stirred for 18 h at 155° C. After cooling, the reaction mixture was diluted with water (100 mL) and extracted with EtOAc (3×25 mL). The combined organic layers were washed with brine, dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography using hexane/EtOAc (1:9, v/v) to afford the product (243 mg, 38%) as a white solid: 1H NMR (300 MHz, DMSO-d6) δ 1.24 (s, 9H), 1.97 (s, 3H), 2.03 (s, 3H), 4.48 (s, 2H) 7.14-7.32 (m, 4H). ES-MS m/z 244.2 (MH+); HPLC RT (min) 1.17.

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionextracted with EtOAc (3×25 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5ecb44264f99436ea8a77c7ed7aa835e
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07265144B2

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