HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dichloromethane → HCID 11965784, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | (Pyrimidin-5-yl)boronic acid | HCID 2795193 | — |
| Reactant | Methyl 2-amino-5-iodo-4-(trifluoromethyl)benzoate | HCID 53436880 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 11965784 | HCID 11965784 | 41% |
Reaction Steps
To a solution of 2-amino-5-iodo-4-trifluoromethyl-benzoic acid methyl ester (1.5 g, 4.35 mmol) in DME (50 mL) were added pyrimidine-5-boronic acid (538.7 mg, 4.35 mmol), Pd(dppf)Cl2.CH2Cl2 (355 mg, 0.43 mmol), Cs2CO3 (2.8 g, 8.7 mmol) and the resultant mixture was stirred at reflux temperature for 36 h. The solvent was removed in vacuo and the residue was purified by flash chromatography (120 g silica gel, hexanes→EtOAc/hexanes (3:7 to 1:1)) to furnish the title product (528 mg, 41%) as a beige solid. API-ES: m/z 298 [M+H]+, rt 4.06 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08513268B2 |
| Source dataset | uspto-grants-2013_08 |
| ORD ID | ord-c6eda55d83074bd09800df72aa679a3b |
| Source note | uspto-grants-2013_08 |