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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1772592Generated: October 27, 2026

2-Methylquinoline → (E)-4-(5-Bromo-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-a]pyrazin-8-yl)morpholine

https://huagongshe.com/reaction/1772592

Reaction equation

Participants

RoleNameHCIDCharge
Reactant2-MethylquinolineHCID 7060—
ReactantBromotrimethylsilaneHCID 76113—
Reactant5-Bromo-8-morpholinoimidazo[1,2-a]pyrazine-2-carbaldehydeHCID 117728113—
SolventDimethylformamideHCID 6228—
Product(E)-4-(5-Bromo-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-a]pyrazin-8-yl)morpholineHCID 11772850593.3%

Reaction Steps

To a solution of compound 2a (800 mg, 2.58 mmol) in DMF (10 mL) was added 2-methylquinoline (600 mg, 4.20 mmol) and bromotrimethylsilane (960 mg, 8.89 mmol). The reaction mixture was stirred in a 20 mL sealed tube at 90° C. for 4 h. After cooling to rt, the reaction was quenched with MeOH (20 mL). The solids were collected by filtration and washed with Et2O to obtain compound 2b as a red solid (1.05 g, 85% yield). Mass Spectrum (LCMS, ESI pos.): Calcd. for C21H18BrN5O: 436.1 (M+H). found: 436.1.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09249163B2
Source datasetuspto-grants-2016_02
ORD IDord-d0ae6533bf0f44439cb6e447ce92593d
Source noteuspto-grants-2016_02