Potassium Carbonate → Tert-butyl 2-(3-carbamoyl-1H-indazol-1-yl)acetate

HRID 1527286Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1527286
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([NH2:12])=[O:11])=[N:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]>CC#N>[C:10]([C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[N:1]([CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[N:2]=1)(=[O:11])[NH2:12]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 209781761H-Indazole-3-carboxamide

Produkt 1

HCID 68283122Tert-butyl 2-(3-carbamoyl-1H-indazol-1-yl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a suspension of 1H-indazole-3-carboxamide [90004-04-9] (2.00 g, 12.4 mmol) and potassium carbonate (4.12 g, 29.8 mmol) in CH3CN (60 mL) was added tert-butyl bromoacetate (2.20 mL, 14.9 mmol) dropwise at RT, and the resulting mixture was heated to reflux for 16 h. The mixture was then cooled to RT and filtered, the solid was washed with CH3CN and the filtrate was concentrated under vacuum. The residual oil was used directly in the next reaction step without further purification. MS (LC/MS): 276.0 [M+H]+; tR (HPLC conditions k): 3.22 min.

Aufarbeitung

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 16 h
  3. filtrationfiltered
  4. washthe solid was washed with CH3CN
  5. concentrationthe filtrate was concentrated under vacuum
  6. customThe residual oil was used directly in the next reaction step without further purification
  7. custom3.22 min.

Quellen und Nachweise

ORD-Eintrag
ord-a63fad99920b4b25b58bd53160f63a8a
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09085555B2

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