Sodium Hydroxide → 3-[2,6-Dimethoxy-4-(methoxymethyl)phenyl]-6-(methylsulfonyl)pyrazolo[5,1-b][1,3]thiazole

HRID 41268

Reaktionsgleichung

Br[C:2]1[CH:22]=[C:5]2[S:6][CH:7]=[C:8]([C:9]3[C:14]([O:15][CH3:16])=[CH:13][C:12]([CH2:17][O:18][CH3:19])=[CH:11][C:10]=3[O:20][CH3:21])[N:4]2[N:3]=1.[CH3:23][S:24]([O-:26])=[O:25].[Na+].N1CCC[C@H]1C(O)=O.[OH-].[Na+]>[Cu](I)I.O.CS(C)=O>[CH3:21][O:20][C:10]1[CH:11]=[C:12]([CH2:17][O:18][CH3:19])[CH:13]=[C:14]([O:15][CH3:16])[C:9]=1[C:8]1[N:4]2[N:3]=[C:2]([S:24]([CH3:23])(=[O:26])=[O:25])[CH:22]=[C:5]2[S:6][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 140 °C

Versuchsvorschrift

To a dimethyl sulfoxide (28.0 mL) solution of 6-bromo-3-[2,6-dimethoxy-4-(methoxymethyl)phenyl]pyrazolo[5,1-b][1,3]thiazole (1.12 g, 2.92 mmol) were added sodium methanesulphinate (2.38 g, 23.3 mmol), L-proline (268 mg, 2.33 mmol), sodium hydroxide (184 mg, 4.61 mmol), and copper iodide (444 mg, 2.33 mmol) and the mixture was heated at 140° C. for three hours by using Biotage Initiator™ Microwave Synthesizer. After the reaction was completed, water was added, the reaction mixture was extracted with ethyl acetate, the organic layer was dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. To the residue, ethyl acetate was added, and the obtained solid was subjected to suction filtration and dried to obtain the title compound (1.00 g, 2.62 mmol).

Aufarbeitung

extractionthe reaction mixture was extracted with ethyl acetate
dry with materialthe organic layer was dried over magnesium sulfate
distillationthe solvent was distilled off under reduced pressure
additionTo the residue, ethyl acetate was added
filtrationthe obtained solid was subjected to suction filtration
customdried

Quellen und Nachweise

ORD-Eintrag: ord-b3466e03091f4f59a6c842bb8b7abe9c
Quelldatensatz: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08530504B2

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