Sodium Hydroxide → 3-[2,6-Dimethoxy-4-(methoxymethyl)phenyl]-6-(methylsulfonyl)pyrazolo[5,1-b][1,3]thiazole
Reaction equation
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]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 140 °C
Procedure
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).
Workup
- 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
Sources & evidence
- ORD record
- ord-b3466e03091f4f59a6c842bb8b7abe9c
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08530504B2
Reaction notes
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