Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1H-Indazol-5-amine | HCID 88012 | — |
| Reactant | Ethyl 1-bromocyclobutanecarboxylate | HCID 97595 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 67336209 | HCID 67336209 | 17.3% |
Reaction Steps
A mixture of 1H-indazol-5-ylamine (5.0 g, 37.6 mmol), ethyl 1-bromocyclobutane carboxylate (7.78 g, 6.08 mL, 37.6 mmol) and triethylamine (7.60 g, 10.5 mL, 75.1 mmol) in ethanol (5 mL) was heated at 100° C. for 3 days, then at 140° C. for 2 days. The reaction mixture was cooled to ambient temperature, and after 7 days the mixture was diluted with DCM (50 mL) and filtered. The filtrate was concentrated in vacuo then purified by chromatography (silica, 2 to 10% of a 9:1 MeOH:NH4OH solution in DCM) to give 1-(1H-indazol-5-ylamino)-cyclobutanecarboxylic acid ethyl ester (1.68 g, 6.49 mmol, 17%) as an oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07998963B2 |
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| Source dataset | uspto-grants-2011_08 |
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| ORD ID | ord-dc4aaaf3f78943f8886051a335932779 |
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| Source note | uspto-grants-2011_08 |
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