Potassium Carbonate → HCID 178437994, Verbindung

HRID 1520020Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1520020
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[N:19](C(OC(C)(C)C)=O)[N:18]=[C:17]3[C:30]#[C:31][Si](C)(C)C)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CCO>[C:30]([C:17]1[C:16]2[C:20](=[CH:21][CH:22]=[C:14]([CH:11]3[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10]3)[CH:15]=2)[NH:19][N:18]=1)#[CH:31]

Komponenten

4

Edukt 2

HCID 11430Potassium CarbonateHCID 67981297tert-butyl 5-[1-(tert-butoxycarbonyl)piperidin-4-yl]-3-[(trimethylsilyl)ethynyl]-1H-indazole-1-carboxylate

Produkt 1

HCID 178437994HCID 178437994, VerbindungAusbeute 95,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of tert-butyl 5-[1-(tert-butoxycarbonyl)piperidin-4-yl]-3-[(trimethylsilyl)ethynyl]-1H-indazole-1-carboxylate (189 mg; 0.38 mmol; 1.0 eq.) and potassium carbonate (5.3 mg; 0.04 mmol; 0.1 eq.) in EtOH (3.8 mL) was stirred at RT O/N. EtOH was removed under reduced pressure and the residue was diluted with ether, washed with water then brine, dried over magnesium sulfate, filtered and concentrated. The crude was purified by flash chromatography on silica (heptane/EtOAc, gradient from 90:10 to 60:40) to give the title compound as a beige solid (118 mg, 95%). 1H NMR (300 MHz, DMSO-d6) δ 13.35 (brs, 1H), 7.55-7.47 (m, 2H), 7.33 (dd, J=1.6, 8.6 Hz, 1H), 4.48 (s, 1H), 4.15-4.03 (m, 2H), 2.93-2.71 (m, 3H), 1.86-1.74 (m, 2H), 1.65-1.45 (m, 2H), 1.42 (s, 9H). HPLC (Condition A): Rt 4.78 min (purity 99.1%).

Aufarbeitung

  1. customEtOH was removed under reduced pressure
  2. additionthe residue was diluted with ether
  3. washwashed with water
  4. dry with materialbrine, dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude was purified by flash chromatography on silica (heptane/EtOAc, gradient from 90:10 to 60:40)

Quellen und Nachweise

ORD-Eintrag
ord-b15e35665bd7400c91a3772a6a740413
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073892B2

Notizen zur Reaktion

Wird geladen…