Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Lithium iodide | HCID 66321 | — |
| Reactant | HCID 71284381 | HCID 71284381 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 71281737 | HCID 71281737 | 94% |
Reaction Steps
To a solution of methyl 6-(4-(benzyloxy)-1-methyl-1H-indol-5-yl)-5-ethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxylate (0.0387 g, 0.09 mmol) in EtOAc (0.5 mL) was added LiI (0.0360 g, 0.27 mmol). The reaction mixture was stirred and heated at 60° C. for 1 h until complete consumption of starting material was observed. The mixture was then cooled to room temperature and acidified with aqueous HCl (1M, 1.0 mL) to pH˜2. The product was extracted with EtOAc (3×3 mL). The organic phase was dried over Na2SO4. Upon removal of the solvent 6-(4-(benzyloxy)-1-methyl-1H-indol-5-yl)-5-ethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxylic acid was obtained as a yellow foam (0.0352 g, 94%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09409905B2 |
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| Source dataset | uspto-grants-2016_08 |
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| ORD ID | ord-990bc55b43fd45f191da84ae2e92d7e8 |
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| Source note | uspto-grants-2016_08 |
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