Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sulfuric Acid | HCID 1118 | — |
| Reactant | Lithium Hexamethyldisilazide | HCID 2733832 | — |
| Reactant | 5-fluoro-1,3-dihydro-2H-indol-2-one | HCID 3731012 | — |
| Reactant | HCID 58478790 | HCID 58478790 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 67314636 | HCID 67314636 | 46% |
Reaction Steps
A solution of 5-fluoro-1,3-dihydro-indol-2-one (141 mg, 0.93 mmol.) in THF (4 mL) is treated with a solution of lithium bis(trimethylsilyl)amide (1.9 mL of a 1 M solution in THF, 1.9 mmol) dropwise. The resulting solution is stirred at room temperature for 10 min. A solution of 2-(2,2-dimethoxy-ethyl)-7H-furo[3,4-b]pyridin-5-one (104 mg, 0.47 mmol in THF (1 mL) is added dropwise to the reaction mixture. The resulting solution is stirred for 1.5 h and is then poured into cold aqueous 2N H2SO4 solution (10 mL) at 0° C. The resulting mixture is heated at 45° C. for 30 min and then cooled to room temperature and stirred overnight. The reaction mixture is poured into ice water (150 mL) and stirred for 2h. The solid which formed is collected to give the title compound as a brown solid (76 mg, 46%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07977351B2 |
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| Source dataset | uspto-grants-2011_07 |
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| ORD ID | ord-0798566e85ab462c8bd865c4a799c977 |
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| Source note | uspto-grants-2011_07 |
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