Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Lithium Hexamethyldisilazide | HCID 2733832 | — |
| Reactant | 5-fluoro-1,3-dihydro-2H-indol-2-one | HCID 3731012 | — |
| Reactant | HCID 86618511 | HCID 86618511 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 76798892 | HCID 76798892 | 36.3% |
Reaction Steps
A solution of 5-fluoro-1,3-dihydro-indol-2-one (2.88 g, 19.1 mmol.) in THF (20 mL) is cooled to 0° C. under an argon atmosphere and treated with a solution of lithium bis(trimethylsilyl)amide (38 mL of a 1 M solution in THF, 38.0 mmol) dropwise. The resulting solution is stirred at 0° C. for 10 min and warmed room temperature. A solution of 6,7-dichloro-1-propyl-1H-furo[3,4-c]pyridin-3-one, (3.13 g, 12.72 mmol) in THF (20 mL) is added dropwise to the reaction mixture. The resulting solution is stirred for 4 h. The reaction mixture is poured into aqueous 10% HCl solution (350 mL). The resulting mixture is heated to 90° C. for 2 h and then stirred at room temperature for 36 h. The precipitate which formed is collected by filtration and washed with small volumes of ethyl acetate (10×3 mL) to give the title compound as a yellow solid (1.75 g, 36%).
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-88d79e020cb74561a7da7bdb0d13574a |
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| Source note | uspto-grants-2011_07 |
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