HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → 2-(4-Trifluoromethyl-phenyl)-thiazole-5-carboxylic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-(Trifluoromethyl)phenylboronic acid | HCID 2734389 | — |
| Reactant | Ethyl 2-bromothiazole-5-carboxylate | HCID 3614103 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | 2-(4-Trifluoromethyl-phenyl)-thiazole-5-carboxylic acid ethyl ester | HCID 21051249 | 35.7% |
Reaction Steps
To a solution of ethyl 2-bromothiazole-5-carboxylate (39 μl, 0.26 mmol) in toluene (2 mL) were added 4-(trifluoromethyl)phenylboronic acid (60 mg, 0.32 mmol), 2M Na2CO3(390 μl, 0.78 mmol), and catalytic amounts of Pd(PPh3)4 (61 mg, 0.05 mmol). The reaction mixture was refluxed for 6 hrs, diluted with water and extracted with EtOAc. The extracts were washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by column chromatography on silica gel (EtOAc/n-Hex=1:5) to give title compound (28 mg, 30%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08691855B2 |
| Source dataset | uspto-grants-2014_04 |
| ORD ID | ord-bce351a243e443da99061ca3bf0876e5 |
| Source note | uspto-grants-2014_04 |