Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Lithium hydroxide, monohydrate | HCID 168937 | — |
| Reactant | HCID 86281771 | HCID 86281771 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | MeOH tetrahydrofuran | HCID 21899815 | — |
| Product | HCID 86281900 | HCID 86281900 | 62% |
Reaction Steps
Ethyl-2-(5-(3,5-dimethyl isoxazol-4-yl)-2-oxo-3-phenylindolin-3-yl)acetate (35 mg, 0.089 mmol) dissolved in THF/MeOH (2 mL/2 mL) was added LiOH.H2O (40 mg) in H2O (2 mL). The reaction was stirred at room temperature until complete consumption of the starting material as indicated by TLC. The reaction was added water, acidified with 3% HCl until pH<1 and extracted with EtOAc (3×5 mL). The combined extracts were washed with brine, dried over MgSO4 and concentrated under vacuum. The title compound was purified on Pre-TLC to afford the title compound as a white solid (20 mg, 62%). 1H NMR (400 MHz, DMSO-d6) δH 12.17 (s, 1H), 10.56 (s, 1H), 7.41 (s, 1H), 7.35-7.29 (m, 4H), 7.22-7.24 (m, 2H), 6.96 (d, J=8.0 Hz, 1H), 3.29-3.30 (m, 2H), 2.38 (s, 3H), 2.21 (s, 3H). MS (ESI) m/e [M+1]+ 363.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09393232B2 |
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| Source dataset | uspto-grants-2016_07 |
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| ORD ID | ord-619a2d4555fb4c55829af709418c1488 |
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| Source note | uspto-grants-2016_07 |
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