Potassium Carbonate → HCID 59234717, Verbindung

HRID 424134

Reaktionsgleichung

Reaktionsgleichung von HRID 424134
[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([CH:15]=[CH:16][CH:17]=2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:5]=[C:4]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].Cl[C:29]([O:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:30]>C1COCC1>[C:18]([C:4]1[CH:3]=[C:2]([NH:1][C:29]([O:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:30])[N:6]([C:7]2[CH:8]=[C:9]([CH:15]=[CH:16][CH:17]=2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:5]=1)([CH3:20])([CH3:19])[CH3:21]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 15891Phenyl chloroformateHCID 21867322ethyl 3-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)benzoate

Produkt 1

HCID 59234717HCID 59234717, VerbindungAusbeute 92,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of ethyl 3-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)benzoate (60 g, 208.8 mmol) and K2CO3 (86.6 g, 626.4 mmol) in THF (1400 mL) was added phenyl chloroformate (98.1 g, 626.4 mmol). The reaction was stirred at room temperature overnight. The solid was removed by filtration and most of the solvent was evaporated under reduced pressure. The residual mixture was dissolved in EtOAc and washed with brine, then water. The organic layer was then dried and concentrated. The crude product was purified by recrystallization from CH2Cl2/hexanes to give the desired product as a white powder (78.5 g, 92%). MS m/z 408.1 (M+H)+; calcd. mass 407. Retention time (LC-MS): 3.92 min. 1H-NMR (DMSO-d6): δ 10.19 (s, broad, 1H); 8.11 (m 1H); 7.97 (d, J=7.6 Hz, 1H); 7.86 (m, 1H); 7.71 (t, 1H); 7.38 (m, 2H); 7.24 (m, 1H); 7.08 (m, 1H); 6.40 (s, 1H); 4.38 (q, 2H); 1.32 (t, 3H); 1.29 (s, 9H).

Aufarbeitung

  1. customThe solid was removed by filtration and most of the solvent
  2. customwas evaporated under reduced pressure
  3. dissolutionThe residual mixture was dissolved in EtOAc
  4. washwashed with brine
  5. customThe organic layer was then dried
  6. concentrationconcentrated
  7. customThe crude product was purified by recrystallization from CH2Cl2/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-12ff4ae12346482cab4ca44429cc8589
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101773B2

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