Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-Fluorophenylboronic acid | HCID 285645 | — |
| Reactant | 2-Bromo-6,7-dihydrothieno[3,2-c]pyridin-4(5H)-one | HCID 56972289 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Hexane | HCID 8058 | — |
| Product | HCID 66801724 | HCID 66801724 | 88% |
Reaction Steps
(4-Fluoro-phenyl)-dihydroxy-borane (232 mg, 1.66 mmol) was added to a stirred suspension of 2-bromo-6,7-dihydro-5H-thieno[3,2-c]pyridin-4-one (I-14d: 300 mg, 1.38 mmol) and Na2CO3 (211.8 mg, 2.0175 mmol) in toluene (20 mL) and water (3 mL) with continuous argon purging. This was followed by the addition of Pd(PPh3)4 (159 mg, 0.138 mmol) and the resulting mixture was stirred at 100° C. overnight. The reaction was monitored by TLC (50% ethylacetate in hexane). The reaction mixture was filtered; the filtrate was washed with water, dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (30% ethylacetate in hexane) afforded 300 mg of the product (88% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08946260B2 |
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| Source dataset | uspto-grants-2015_02 |
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| ORD ID | ord-f043798b35b241eda810b60166a43718 |
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| Source note | uspto-grants-2015_02 |
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