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Potassium Carbonate → HCID 10158642, Verbindung

HRID 899390
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 899390
[N:1]1[O:2][N:3]=[C:4]2[CH:9]=[C:8]([O:10][C:11]3[N:30]=[CH:29][CH:28]=[CH:27][C:12]=3[C:13]([NH:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([C:23](O)([CH3:25])[CH3:24])=[CH:19][CH:18]=3)=[O:14])[CH:7]=[CH:6][C:5]=12.C[Si]([C:35]#[N:36])(C)C.[Sn](Cl)(Cl)(Cl)Cl.C(=O)([O-])[O-].[K+].[K+].O.O.[F-].[K+]>ClCCl.O>[N:1]1[O:2][N:3]=[C:4]2[CH:9]=[C:8]([O:10][C:11]3[N:30]=[CH:29][CH:28]=[CH:27][C:12]=3[C:13]([NH:15][CH2:16][C:17]3[CH:18]=[CH:19][C:20]([C:23]([C:35]#[N:36])([CH3:25])[CH3:24])=[CH:21][CH:22]=3)=[O:14])[CH:7]=[CH:6][C:5]=12
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

HCID 11430Potassium CarbonateHCID 24287Tin tetrachlorideHCID 82115Trimethylsilyl cyanideHCID 98659292-(2,1,3-Benzoxadiazol-5-yloxy)-N-((4-(1-hydroxy-1-methylethyl)phenyl)methyl)-3-pyridinecarboxamideHCID 23708904Potassium fluoride dihydrate

Produkt 1

HCID 10158642
HCID 10158642, Verbindung
Ausbeute 40,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 2-(benzo[2,1,3]oxadiazol-5-yloxy)-N-[4-(1-hydroxy-1-methyl-ethyl)-benzyl]-nicotinamide (300 mg, 0.74 mmol) in dichloromethane (1.5 ml) cooled to 0° C. was added trimethylsilyl cyanide (1 ml, 7.4 mmol) followed by slow addition of tin tetrachloride (7 drops of a 1.0 M solution in dichloromethane). The reaction mixture was allowed to warm to room temperature overnight. Potassium carbonate (300 mg, 2.10 mmol) and potassium fluoride dihydrate (120 mg, 2.10 mmol) were added, followed by dropwise addition of water. The reaction mixture was stirred vigorously for 90 m., after which silica gel was (600 mg) added. The mixture was filtered and washed thoroughly with dichloromethane. The filtrate was washed with saturated aqueous sodium bicarbonate, dried over magnesium sulfate, filtered and concentrated to give 124 mg of a pale yellow solid. Product was recrystallized from ethyl acetate/hexane to afford 96 mg (31% yield) of a pale yellow solid.

Aufarbeitung

  1. additionadded
  2. filtrationThe mixture was filtered
  3. washwashed thoroughly with dichloromethane
  4. washThe filtrate was washed with saturated aqueous sodium bicarbonate
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a64eaedaea9147e98dd4d01ceb404108
Quelldatensatz
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07354941B2

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