Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Ethyl 3-oxo-2,3-dihydro-1H-indazole-1-carboxylate | HCID 584113 | — |
| Reactant | 2-(chloromethyl)-1-methyl-1H-imidazole | HCID 736536 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 19805500 | HCID 19805500 | 67% |
Reaction Steps
2-Chloromethyl-1-methylimidazole (0.91 g) was added portionwise to a stirred mixture of 1,2-dihydro-1-carboethoxy-3H-indazol-3-one (1.03 g), caesium carbonate (5.4 g) and N,N-dimethylformamide (DMF, 5 ml). The mixture was heated to 80° C. for 4 hours under an atmosphere of argon, cooled to ambient temperature and filtered. The filtrate was diluted with water and extracted with ethyl acetate. The solid was washed with ethyl acetate. The organic solutions were combined, washed with a saturated aqueous sodium chloride solution, dried (MgSO4) and evaporated. The oil residue crystallised on trituration under diethyl ether. There was thus obtained a mixture (1 g, 67% of 1,2-dihydro-1-carboethoxy-2-(1-methylimidazol-2-yl)methyl-3H-indazol-3-one and 1-carboethoxy-3-(1-methylimidazol-2-yl)methoxy-1H-indazole (starting material for Ex. 145).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05173496 |
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| Source dataset | uspto-grants-1992_12 |
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| ORD ID | ord-88a00675ace7406b80429698b46d43a3 |
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| Source note | uspto-grants-1992_12 |
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