Sodium Bicarbonate → 4-Chloro-1-ethyl-N-[1-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-yl]-1H-pyrazole-5-carboxamide

HRID 244691Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 244691
[Cl:1][C:2]1[CH:3]=[N:4][N:5]([CH2:10][CH3:11])[C:6]=1[C:7](Cl)=[O:8].[C:12]1([S:18]([N:21]2[C:29]3[CH:28]=[C:27]([Sn:30]([CH3:33])([CH3:32])[CH3:31])[CH:26]=[C:25]([NH2:34])[C:24]=3[CH:23]=[N:22]2)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl.N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[N:4][N:5]([CH2:10][CH3:11])[C:6]=1[C:7]([NH:34][C:25]1[CH:26]=[C:27]([Sn:30]([CH3:33])([CH3:32])[CH3:31])[CH:28]=[C:29]2[C:24]=1[CH:23]=[N:22][N:21]2[S:18]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:20])=[O:19])=[O:8]

Komponenten

6

Edukt 3

HCID 516892Sodium BicarbonateHCID 252208134-chloro-1-ethyl-1H-pyrazole-5-carbonyl chlorideHCID 582557431-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-amine

Produkt 1

HCID 583564294-Chloro-1-ethyl-N-[1-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-yl]-1H-pyrazole-5-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

4-Chloro-1-ethyl-1H-pyrazole-5-carbonyl chloride (122 mg) in DCM (5 ml) was added over 5 min to 1-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-amine (250 mg) in DCM (10 ml) and pyridine (0.05 ml). The reaction was stirred at room temperature for 1.5 h. Saturated sodium bicarbonate (aq) (20 ml) was added and the reaction stirred vigorously before the DCM was passed through a hydrophobic frit and evaporated to dryness. The residue was passed through a silica cartridge, preconditioned with cyclohexane. The silica cartridge was washed with cyclohexane:diethyl ether (1:1, v/v), then diethyl ether. The product containing ether fraction was evaporated to dryness to give title compound, 303 mg.

Aufarbeitung

  1. customevaporated to dryness
  2. washThe silica cartridge was washed with cyclohexane:diethyl ether (1:1
  3. additionThe product containing ether fraction
  4. customwas evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-fb6a58974129415e97f9f22e8e12aa62
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658635B2

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