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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2215921Generated: October 25, 2026

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

https://huagongshe.com/reaction/2215921

Reaction equation

Participants

RoleNameHCIDCharge
Reactant3-Amino-4-(trifluoromethyl)pyridineHCID 2735957—
ReactantSodium t-butoxideHCID 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 esterHCID 58700289—
Reactant5-Methyl-8-(pyridinylamino)-6-trifluoromethyl-1,3,4,4a,5,9b-hexahydro-pyrido[4,3-b]indole-2-carboxylic acid tert-butyl esterHCID 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-carbonitrileHCID 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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07109339B2
Source datasetuspto-grants-2006_09
ORD IDord-d5abb7455b64411aa51ceff984d8922b
Source noteuspto-grants-2006_09