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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1612210Generated: November 2, 2026

(2-Chloro-4-methylphenyl)boronic acid → 5-(2-chloro-4-methylphenyl)-N-(3,4-dihydro-2H-chromen-4-yl)-3,6-diethylpyrazin-2-amine

https://huagongshe.com/reaction/1612210

Reaction equation

Participants

RoleNameHCIDCharge
Reactant(2-Chloro-4-methylphenyl)boronic acidHCID 2773334—
Reactant5-bromo-N-(3,4-dihydro-2H-chromen-4-yl)-3,6-diethylpyrazin-2-amineHCID 22147267—
Reactant(1R,2S)-1-{[5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-yl]amino}-2,3-dihydro-1H-inden-2-olHCID 58583246—
CatalystTetrakis(triphenylphosphine)palladiumHCID 11979704—
Solvent1,2-DimethoxyethaneHCID 8071—
Product5-(2-chloro-4-methylphenyl)-N-(3,4-dihydro-2H-chromen-4-yl)-3,6-diethylpyrazin-2-amineHCID 10237795—

Reaction Steps

Following the procedure for the preparation of (1R,2S)-1-{[5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-yl]amino}-2,3-dihydro-1H-inden-2-ol but substituting 5-bromo-N-(3,4-dihydro-2H-chromen-4-yl)-3,6-diethylpyrazin-2-amine, ethylene glycol dimethyl ether, 2-chloro-4-methyl phenyl boronic acid and tetrakis(triphenylphosphine) palladium and making non-critical variations provided the title compound as a oil: 1H NMR (300 MHz, CDCl3) δ) 7.37-7.13, 6.99-6.90, 5.37, 4.64, 4.31, 2.69, 2.54, 2.40, 2.30, 1.29-1.17; HRMS (FAB) calcd for C24H26ClN3O+H 408.1842, found 408.1848. Anal. Calcd for C24H26ClN3O: C, 70.66; H, 6.42; N, 10.30. Found: C, 70.93; H, 6.78; N, 10.01.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06992087B2
Source datasetuspto-grants-2006_01
ORD IDord-2a5576a25b4d434e86c41123c169ec87
Source noteuspto-grants-2006_01