HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-Amino-4-(trifluoromethyl)pyridine → (4aS,9bR)-5-methyl-8-(4-trifluoromethyl-pyridin-3-ylamino)-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole-6-carbonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-Amino-4-(trifluoromethyl)pyridine | HCID 2735957 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Reactant | (4aS,9bR)-8-bromo-6-cyano-5-methyl-1,3,4,4a,5,9b-hexahydro-pyrido[4,3-b]indole-2-carboxylic acid tert-butyl ester | HCID 58700289 | — |
| Reactant | 5-Methyl-8-(pyridinylamino)-6-trifluoromethyl-1,3,4,4a,5,9b-hexahydro-pyrido[4,3-b]indole-2-carboxylic acid tert-butyl ester | HCID 67183531 | — |
| Product | (4aS,9bR)-5-methyl-8-(4-trifluoromethyl-pyridin-3-ylamino)-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole-6-carbonitrile | HCID 58700425 | — |
Reaction Steps
The title compound was prepared by following the general method for (5-methyl-6-trifluoromethyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indol-8-yl)-pyridin-3-yl-amine (Method A) as a yellow solid (50 mg, 26%) from (4aS,9bR)-8-bromo-6-cyano-5-methyl-1,3,4,4a,5,9b-hexahydro-pyrido[4,3-b]indole-2-carboxylic acid tert-butyl ester (Example 158, 196 mg, 0.5 mmol), 4-trifluoromethyl-pyridin-3-ylamine (141 mg, 1.5 mmol) and NaOt-Bu (144 mg, 1.5 mmol). MS (ESI): 374 (base, M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07109339B2 |
| Source dataset | uspto-grants-2006_09 |
| ORD ID | ord-d5abb7455b64411aa51ceff984d8922b |
| Source note | uspto-grants-2006_09 |