HuagongsheHuagongshe Chemistry Print Report · For research reference only
(2-Chloro-4-methylphenyl)boronic acid → 5-(2-chloro-4-methylphenyl)-N-(3,4-dihydro-2H-chromen-4-yl)-3,6-diethylpyrazin-2-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | (2-Chloro-4-methylphenyl)boronic acid | HCID 2773334 | — |
| Reactant | 5-bromo-N-(3,4-dihydro-2H-chromen-4-yl)-3,6-diethylpyrazin-2-amine | HCID 22147267 | — |
| Reactant | (1R,2S)-1-{[5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-yl]amino}-2,3-dihydro-1H-inden-2-ol | HCID 58583246 | — |
| Catalyst | Tetrakis(triphenylphosphine)palladium | HCID 11979704 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | 5-(2-chloro-4-methylphenyl)-N-(3,4-dihydro-2H-chromen-4-yl)-3,6-diethylpyrazin-2-amine | HCID 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
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06992087B2 |
| Source dataset | uspto-grants-2006_01 |
| ORD ID | ord-2a5576a25b4d434e86c41123c169ec87 |
| Source note | uspto-grants-2006_01 |