HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Phosphate, Tribasic → 3-Methanesulfonyl-2-methyl-4-morpholin-4-yl-6-((1R,2R)-2-phenyl-cyclopropyl)-quinoline
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | Trans-2-phenylcyclopropylboronic acid | HCID 11062695 | — |
| Reactant | 6-Bromo-3-methanesulfonyl-2-methyl-4-morpholin-4-yl-quinoline | HCID 12001810 | — |
| Catalyst | Tetrakis(triphenylphosphine)palladium | HCID 11979704 | — |
| Product | 3-Methanesulfonyl-2-methyl-4-morpholin-4-yl-6-((1R,2R)-2-phenyl-cyclopropyl)-quinoline | HCID 12001803 | 61.3% |
Reaction Steps
6-Bromo-3-methanesulfonyl-2-methyl-4-morpholin-4-yl-quinoline (compound of example 6) (300 mg, 0.78 mmol), trans-2-phenylcyclopropylboronic acid (189 mg, 1.17 mmol), potassium phosphate (496 mg, 2.33 mmol) and tetrakis(triphenylphosphine)-palladium (27 mg, 0.023 mmol) were heated at reflux under argon for 8 h. The crude product was purified by chromatography on silica gel in dichloromethane/ethyl acetate 5:1 with a gradient from 100:0 to 80:20. One obtained 202 mg (60%) of white crystals. MS: m/z=423 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07728142B2 |
| Source dataset | uspto-grants-2010_06 |
| ORD ID | ord-11d352aca3c44b14a156a9edbe2e1959 |
| Source note | uspto-grants-2010_06 |