Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | (3-Cyano-5-fluorophenyl)boronic acid | HCID 23435605 | — |
| Reactant | Ethyl 5-bromo-4-(3-chlorophenyl)-1,3-thiazole-2-carboxylate | HCID 70801641 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 70341698 | HCID 70341698 | — |
Reaction Steps
At room temperature, 7.2 ml of an aqueous 2M sodium carbonate solution and 167 mg (0.144 mmol) of tetrakis(triphenylphosphine)palladium are added to 1.00 g (2.89 mmol) of the compound from Example 5A and 714 mg (4.33 mmol) of the boronic acid from Example 22A in 40 ml of DME, and the mixture is subsequently stirred at 80° C. for 24 h. A saturated aqueous ammonium chloride solution is added, and the reaction mixture is subsequently extracted with dichloromethane. The organic phase is dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue is purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient). 606 mg (53% of theory) of the title compound having a purity of 90% are obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08575357B2 |
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| Source dataset | uspto-grants-2013_11 |
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| ORD ID | ord-152ee68b846f409b85961a50caac29ed |
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| Source note | uspto-grants-2013_11 |
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