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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 29107Generated: October 25, 2026

Ethyl Acetate → N-tert-butyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine

https://huagongshe.com/reaction/29107

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl AcetateHCID 8857—
ReactantTert-Butyl isocyanideHCID 23577—
ReactantAminopyrazineHCID 78747—
Reactant5-Pyridin-2-ylethynyl-thiophene-2-carbaldehydeHCID 86230190—
CatalystScandium(III) triflateHCID 2734571—
SolventChloroformHCID 6212—
SolventDichloromethaneHCID 6344—
ProductN-tert-butyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amineHCID 1160317965%

Reaction Conditions

Temperature80 °C

Reaction Steps

1.32 g (14.1 mmol) of 2-aminopyrazine were dissolved together with 3.00 g (14.1 mmol) of 5-pyridin-2-ylethynyl-thiophene-2-carbaldehyde, 1.59 ml (14.1 mmol) of tert.-butyl-isonitrile and 2.07 g (4.2 mmol) of scandium(III) trifluoromethanesulfonate in chloroform (40 ml). The reaction solution was heated to 80° C. for 60 min in the microwave (800 watt, MLS-Ethos1600) and then diluted with DCM. Washing was then performed with a 1M Na2CO3 solution and a sat. aq. NaCl solution. The mixture was then dried over Na2SO4, filtered and evaporated under a vacuum. 3.43 g (9.2 mmol, 65%) of N-tert-butyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine were obtained by crystallisation of the group from EA.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07420056B2
Source datasetuspto-grants-2008_09
ORD IDord-a86679d007254961b57e7e2291097dfc
Source noteuspto-grants-2008_09