Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Lithium Chloride | HCID 433294 | — |
| Reactant | 2-Fluoropyridine-4-boronic acid | HCID 2783396 | — |
| Reactant | HCID 11710884 | HCID 11710884 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 11675896 | HCID 11675896 | 99.4% |
Reaction Steps
Add 3-(5-bromo-benzo[b]thiophen-2-ylmethyl)-1-cyclohexyl-pyrrolidin-2-one (250 mg, 0.64 mmol), 2-fluoropyridine-4-boronic acid (200 mg, 1 mmol), LiCl (10 eq) and Pd(PPh3)4 (0.05 eq) into a solution of dioxane (10 mL) and 2M Na2CO3 (2 mL) and heat at 80° C. for 1 hour. Pour the reaction mixture into water and extract with ethyl acetate. Dry over sodium sulfate, filter, and concentrate. Purify by silica gel (20-50% ethyl acetate in hexanes) to give the title compound as a pale yellow powder (260 mg, 58%): MS (APCI-pos mode) m/z (rel intensity): 409.2 (M+H, 100%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07834194B2 |
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| Source dataset | uspto-grants-2010_11 |
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| ORD ID | ord-06c0c38f10894d329397b6b084cacf7e |
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| Source note | uspto-grants-2010_11 |
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