Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | 1H-Indazol-5-amine | HCID 88012 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 1-Benzyl-3-methyl-4-piperidone | HCID 560965 | — |
| Catalyst | Acetic Acid | HCID 176 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 17838060 | HCID 17838060 | 65% |
Reaction Steps
1-Benzyl-3-methyl-4-piperidone (152.7 mg), 5-aminoindazole (100 mg), and acetic acid (0.02 ml) were dissolved in methanol (10 ml). Acetic acid (five drops) was added to the solution, and a borane-pyridine complex (0.06 ml) was then added dropwise to the solution at room temperature. The reaction mixture was stirred at room temperature for 18 hr. After the completion of the reaction, a saturated aqueous sodium hydrogencarbonate solution (1 ml) was added thereto, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and saturated brine and was dried over sodium sulfate. The solvent was then removed by distillation under the reduced pressure. The residue was purified by column chromatography [silica gel, chloroform/methanol] to give the title compound (95.3 mg, yield 65%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07217722B2 |
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| Source dataset | uspto-grants-2007_05 |
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| ORD ID | ord-4069827c00824927a7b04b156be64697 |
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| Source note | uspto-grants-2007_05 |
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