Potassium Carbonate → HCID 21027707, compound
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[CH:9][NH:8][N:7]=1)=[O:5])[CH3:2].Br[CH2:12][CH2:13][O:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][O:16]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Li+]>CN1CCCC1=O.C(OCC)(=O)C.O>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:12][CH2:13][O:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)[N:8]=[CH:9][CH:10]=1)=[O:5])[CH3:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
Ethyl-pyrazole-3-carboxylate (980 mg, 7.0 mmol), 2-(2-bromoethoxy)-tetrahydro-2H-pyran (1.57 g, 7.5 mmol), potassium carbonate (1.01 g, 7.3 mmol) and lithium iodide (46.8 mg, 0.35 mmol) were dissolved in 1-methyl-2-pyrrolidinone (10 mL) and the reaction mixture heated to 80° C. for 24 hours. The reaction mixture was allowed to cool for 17 hours and then diluted with a mixture of ethyl acetate:water 1:1 (500 mL). The organic layer was washed with water (3×250 mL), dried over magnesium sulphate and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with cyclohexane:ethyl acetate 90:10 to 80:20 to 75:25 to 50:50. The appropriate fractions were combined and concentrated in vacuo to yield the title product.
Workup
- temperatureto cool for 17 hours
- washThe organic layer was washed with water (3×250 mL)
- dry with materialdried over magnesium sulphate
- concentrationconcentrated in vacuo
- customThe residue was purified by column chromatography on silica gel eluting with cyclohexane:ethyl acetate 90:10 to 80:20 to 75:25 to 50:50
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-bbf47ae488034636ab2450681f511172
- Source dataset
- uspto-grants-2006_06
- Patent number
- US07056934B2
Reaction notes
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