Propargyl bromide → HCID 58500414, Verbindung

HRID 1907140Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1907140
[CH:1]([NH:4][C:5]([C:7]1[C:15]2[C:11](=[CH:12][NH:13][N:14]=2)[CH:10]=[C:9]([CH3:16])[C:8]=1[NH:17][C:18]([C:20]1[N:21]([C:27]2[C:32]([Cl:33])=[CH:31][CH:30]=[CH:29][N:28]=2)[N:22]=[C:23]([O:25][CH3:26])[CH:24]=1)=[O:19])=[O:6])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH2:40](Br)[C:41]#[CH:42].CCOC(C)=O>C1COCC1.O>[CH:1]([NH:4][C:5]([C:7]1[C:15]2[C:11](=[CH:12][N:13]([CH2:42][C:41]#[CH:40])[N:14]=2)[CH:10]=[C:9]([CH3:16])[C:8]=1[NH:17][C:18]([C:20]1[N:21]([C:27]2[C:32]([Cl:33])=[CH:31][CH:30]=[CH:29][N:28]=2)[N:22]=[C:23]([O:25][CH3:26])[CH:24]=1)=[O:19])=[O:6])([CH3:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 7842Propargyl bromideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 178492656HCID 178492656, Verbindung

Produkt 1

HCID 58500414HCID 58500414, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 6-{[2-(3-chloro-pyridin-2-yl)-5-methoxy-2H-pyrazole-3-carbonyl]-amino}-5-methyl-2H-indazole-7-carboxylic acid isopropylamide (500 mg, 1.07 mmol) and K2CO3 (196 mg, 1.6 mmol) in THF (5 mL) was stirred for 1 hour at ambient temperature, and was treated with propargylbromide (120 μL, 1.6 mmol). The resulting reaction mixture was stirred for 24 hours at 60° C. AcOEt and water was added. The phases were separated. The aqueous layer was extracted with AcOEt. The organic layers were washed with water, combined, dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash-chromatography (SiO2, Toluene/AcOEt 7:3) afforded the title compound as a colorless crystalline solid. LC/MS: 506 (M+H)+, 528 (M+Na)+.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. stirringwas stirred for 24 hours at 60° C
  3. customThe phases were separated
  4. extractionThe aqueous layer was extracted with AcOEt
  5. washThe organic layers were washed with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customPurification of the residue by flash-chromatography (SiO2, Toluene/AcOEt 7:3)

Quellen und Nachweise

ORD-Eintrag
ord-da43438a95cc4a4d8ef3c3cc8a137e56
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598078B2

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