Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-Fluorophenylboronic acid | HCID 285645 | — |
| Reactant | HCID 66598996 | HCID 66598996 | — |
| Catalyst | Dichlorobis(triphenylphosphine)palladium | HCID 6102075 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 66599216 | HCID 66599216 | — |
Reaction Steps
3-Bromo-2-(trifluoromethyl)imidazo[1,2-a]pyrazine (I12) (1.330 g, 5 mmol), (4-fluorophenyl)boronic acid (1.049 g, 7.50 mmol), sodium carbonate (2.65 g, 25.00 mmol) and Bis(triphenylphosphine)palladium (II) chloride (0.351 g, 0.500 mmol) were heated at 80° C. for 7 h in water (10 ml) and 1,2-dimethoxyethane (DME) (20 ml). The mixture was passed through a hydromatrix cartridge (Varian, 20 g) and washed through with dichloromethane. The filtrated was concentrated in vacuo to afford a tacky oil. The product was purified by flash chromatography (Isolera, 100 g, 0-100% 2M ammonia in methanol:dichloromethane (1:9)/dichloromethane) to afford product in 2.03 g. The compound was repurified by flash chromatography (Isolera, 100 g, 0-100% ethyl acetate/iso-hexane) to afford product in 1.42 g as beige solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08513248B2 |
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| Source dataset | uspto-grants-2013_08 |
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| ORD ID | ord-32fd4b3a7bb9457990a2a76d2b9614bf |
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| Source note | uspto-grants-2013_08 |
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