Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | 2-Fluorophenylboronic acid | HCID 2734354 | — |
| Reactant | Methyl 1-(5-bromopyrimidin-2-yl)-3-(methylthio)-1H-indole-6-carboxylate | HCID 118666039 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Solvent | Sodium Carbonate | HCID 10340 | — |
| Product | HCID 131735393 | HCID 131735393 | — |
Reaction Steps
Tetrakis(triphenylphosphine)palladium(0) (0.15 g, 0.13 mmol), 2-fluorophenylboronic acid (0.93 g, 6.64 mmol) and ethanol (40 mL) were added under an argon atmosphere to a mixture of 51b) (2.0 g, 5.3 mmol) in DME (40 mL) and 2M sodium carbonate solution (5.3 mL). The resulting mixture was heated at 90° C. for 3 h and then filtered through a pad of celite that was subsequently rinsed with dichloromethane (2×50 mL). The filtrate was concentrated and the remnant purified by column chromatography [100-200 mesh silica; dichloromethane/hexane=1:1]. White solid. Yield: 2.0 g (96% of theory). HPLC-MS (method 5): Rt=4.41 min; m/z [M+H]+=394
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09315490B2 |
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| Source dataset | uspto-grants-2016_04 |
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| ORD ID | ord-b23e21a5b82b462baf13810a155505e1 |
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| Source note | uspto-grants-2016_04 |
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