Potassium Carbonate → phenyl 3-tert-butyl-1-methyl-1H-pyrazol-5-ylcarbamate

HRID 929995Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 929995
[C:1]([C:5]1[CH:9]=[C:8]([NH2:10])[N:7]([CH3:11])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl[C:19]([O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:20]>C1COCC1>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:19](=[O:20])[O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:7]([CH3:11])[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 15891Phenyl chloroformateHCID 27352873-tert-Butyl-1-methyl-1H-pyrazol-5-amine

Produkt 1

HCID 46196890phenyl 3-tert-butyl-1-methyl-1H-pyrazol-5-ylcarbamateAusbeute 39,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of 3-tert-butyl-1-methyl-1H-pyrazol-5-amine (0.75 g, 9.8 mmol) and potassium carbonate (1.76 g, 12.7 mmol) in THF (20 mL) at 0° C. was added dropwise phenyl chloroformate (0.7 mL, 10.8 mmol). The mixture was stirred at rt for 16 h. The mixture was then filtered through celite and solvent was removed under reduced pressure. The crude residue was purified by silica gel flash chromatography, eluting with 0% to 100% EtOAc in hexanes, to afford phenyl 3-tert-butyl-1-methyl-1H-pyrazol-5-ylcarbamate (1.05 g, 39% yield). LCMS (ESI) m/z 348 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 10.11 (br s, 1H), 7.45-7.40 (m, 2H), 7.29-7.21 (m, 3H), 6.04 (s, 1H), 3.58 (s, 3H), 1.20 (s, 9H).

Aufarbeitung

  1. filtrationThe mixture was then filtered through celite and solvent
  2. customwas removed under reduced pressure
  3. customThe crude residue was purified by silica gel flash chromatography
  4. washeluting with 0% to 100% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-c4cb4fa7029c44b7a5dc6648026e64ce
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296722B2

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