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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2215910Generated: October 26, 2026

5-Amino-2-chloropyridine → (4aS,9bR)-(6-Chloro-pyridin-3-yl)-(5-methyl-6-trifluoromethyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indol-8-yl)-amine

https://huagongshe.com/reaction/2215910

Reaction equation

Participants

RoleNameHCIDCharge
Reactant5-Amino-2-chloropyridineHCID 79305—
ReactantSodium t-butoxideHCID 23676156—
Reactant(4aS,9bR)-8-bromo-5-methyl-6-trifluoromethyl-1,3,4,4a,5,9b-hexahydro-pyrido[4,3-b]indole-2-carboxylic acid tert-butyl esterHCID 67182365—
Product(4aS,9bR)-(6-Chloro-pyridin-3-yl)-(5-methyl-6-trifluoromethyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indol-8-yl)-amineHCID 21056600—

Reaction Steps

The title compound was prepared by following the general Method A as a yellow solid (56 mg, 29%) from (4aS,9bR)-8-bromo-5-methyl-6-trifluoromethyl-1,3,4,4a,5,9b-hexahydro-pyrido[4,3-b]indole-2-carboxylic acid tert-butyl ester (Example 45, 217 mg, 0.5 mmol), 5-amino-2-chloro-pyridine (193 mg, 1.5 mmol) and NaOt-Bu (144 mg, 1.5 mmol). MS (ESI): 383 (base, M+H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07109339B2
Source datasetuspto-grants-2006_09
ORD IDord-9fee81abce2b4a8ba45ca6e331390788
Source noteuspto-grants-2006_09