Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Ethyl 5-bromopyridine-3-carboxylate | HCID 140785 | — |
| Reactant | 4-(Trifluoromethyl)phenylboronic acid | HCID 2734389 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 58002512 | HCID 58002512 | — |
Reaction Steps
6.74 g (29.3 mmol) of ethyl 5-bromonicotinate, 8.35 g (43.9 mmol) of 4-trifluoromethylphenylboronic acid, 0.17 g (0.15 mmol) of tetrakis(triphenylphosphine)palladium(0) and 6.21 g (58.6 mmol) of sodium carbonate were dissolved in a mixture of 75 ml of 1,2-dimethoxyethane, 15 ml of water and 184 ml of dimethylformamide and stirred at 85° C. for 18 h. For work-up, some of the dimethylformamide was removed under reduced pressure, and the reaction mixture was diluted with water and extracted with dichloromethane. The organic phase was dried over sodium sulphate and the crude product was purified by flash chromatography (dichloromethane/acetonitrile 100:2→100:5). Yield: 6.22 g (72% of theory)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08119663B2 |
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| Source dataset | uspto-grants-2012_02 |
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| ORD ID | ord-2ac859037919432a8e3ea694a9307288 |
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| Source note | uspto-grants-2012_02 |
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