Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | N-bromobutanimide | HCID 67184 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 66681386 | HCID 66681386 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 66681584 | HCID 66681584 | 60.1% |
Reaction Steps
Ethyl 2-[1-(t-butoxycarbonyl)-1H-pyrrol-2-yl]-1,3-thiazole-5-carboxylate (800 mg, 2.48 mmol) synthesized in Example (5a) was dissolved in tetrahydrofuran (30 mL), and cooled to 0° C. N-Bromosuccinimide (442 mg, 2.48 mmol) was added with stirring under nitrogen atmosphere, and subsequently stirring was carried out at room temperature for 19 hours. A saturated aqueous sodium hydrogencarbonate solution (30 mL) was added, and extraction was carried out with ethyl acetate (30 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=0%-30%) to afford the desired compound (598 mg, yield 60%) as a pale yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08415359B2 |
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| Source dataset | uspto-grants-2013_04 |
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| ORD ID | ord-479be7f1b7374e8cb7c242835297d652 |
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| Source note | uspto-grants-2013_04 |
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