HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → 2-fluoro-N-(3-isopropoxyphenyl)-4-methyl-3-(2-(methylamino)quinazolin-6-yl)benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | N-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)quinazolin-2-amine | HCID 16086139 | — |
| Reactant | 2-fluoro-3-iodo-N-(3-isopropoxyphenyl)-4-methylbenzamide | HCID 58829750 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | 2-fluoro-N-(3-isopropoxyphenyl)-4-methyl-3-(2-(methylamino)quinazolin-6-yl)benzamide | HCID 58829058 | 57.1% |
Reaction Steps
A mixture of 2-fluoro-3-iodo-N-(3-isopropoxyphenyl)-4-methylbenzamide (630 mg, 1525 μmol), N-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinazolin-2-amine (522 mg, 1830 μmol) and sodium carbonate (2 M aqueous solution) (1525 μL, 3049 μmol) in DME (25 mL) was flushed with nitrogen and then tetrakis(triphenylphosphine)palladium (0) (176 mg, 152 μmol) was added. The mixture was refluxed for 24 h and thne cooled to RT. Solvent was removed in vacuo and the residue was purified by flash chromatography eluting with EtOAc/hexane (25-60%) to give the title compound (387 mg, 57%). MS (M+H)+ 445.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08440674B2 |
| Source dataset | uspto-grants-2013_05 |
| ORD ID | ord-e92b329307f5445286d8a336adf92398 |
| Source note | uspto-grants-2013_05 |