Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2-Chloropyridine-4-boronic acid, pinacol ester | HCID 5103408 | — |
| Reactant | Trifluoro-methanesulfonic acid 2-(4-fluoro-phenyl)-cyclohex-1-enyl ester | HCID 86673616 | — |
| Catalyst | HCID 178419050 | HCID 178419050 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 86673617 | HCID 86673617 | 58.3% |
Reaction Steps
Trifluoro-methanesulfonic acid 2-(4-fluoro-phenyl)-cyclohex-1-enyl ester (200 mg, 0.62 mmol), 2-Chloro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine (162 mg, 0.68 mmol), Bis(triphenylphosphine)Palladium (II) dichloride (43 mg, 0.062 mmol), Sodium Carbonate solution (2.0 M, 1.54 mL, 3.1 mmol) and DMF (3 mL) are mixed in a 5 mL microwave tube with a stir bar and the mixture is heated to 100° C. in microwave reactor for 30 min. The mixture is poured to water (10 mL) and extracted with EtOAc (10 mL×3). The organic extracts are washed with water (20 mL×1), brine (20 mL×1) and dried over anhydrous sodium sulfate. After concentration, the crude is purified by silica flash column chromatography using EtOAc in Heptane (gradient from 0% to 20%) to give 104 mg of the desired product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08722709B2 |
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| Source dataset | uspto-grants-2014_05 |
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| ORD ID | ord-f918b3db77804691a76161ae6aea9624 |
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| Source note | uspto-grants-2014_05 |
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