Sulfuric Acid → 1-(5-Iodo-6-methylpyridin-2-yl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester
Reaction equation
S(=O)(=O)(O)O.[CH2:6]([O:8][C:9]([C:11]1[CH:12]=[N:13][N:14]([C:17]2[CH:22]=[CH:21][C:20](N)=[C:19]([CH3:24])[N:18]=2)[C:15]=1[CH3:16])=[O:10])[CH3:7].N([O-])=O.[Na+].[I-:29].[K+].C(=O)(O)[O-].[Na+].S([O-])([O-])=O.[Na+].[Na+]>O>[CH2:6]([O:8][C:9]([C:11]1[CH:12]=[N:13][N:14]([C:17]2[CH:22]=[CH:21][C:20]([I:29])=[C:19]([CH3:24])[N:18]=2)[C:15]=1[CH3:16])=[O:10])[CH3:7]Participants
Reactant 6
Product 1
Reagents, catalysts & solvents 1
Procedure
After concentrated sulfuric acid (20 ml) were added to 1-(5-amino-6-methylpyridin-2-yl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (7.8 g) and water (80 ml) at 0° C., sodium nitrite (3.0 g) was added therein in several portions. After stirring for 0.5 hour, potassium iodide (9.96 g) was added in several portions and the mixture was stirred for 2.5 hours at room temperature. A saturated aqueous solution of sodium bicarbonate was added in several portions at 0° C. and then an aqueous solution of sodium sulfite was added and the aqueous solution was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The resulting solid was washed with ethyl acetate and n-hexane to give the titled compound (7.76 g) as a yellow solid.
Workup
- stirringthe mixture was stirred for 2.5 hours at room temperature
- extractionthe aqueous solution was extracted with ethyl acetate
- washThe organic layer was washed with water and saturated brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated in vacuo
- washThe resulting solid was washed with ethyl acetate and n-hexane
Sources & evidence
- ORD record
- ord-0df563de4d2c4e5faf7d28af19e17545
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09150555B2
Reaction notes
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