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 67315614 | HCID 67315614 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 67313546 | HCID 67313546 | 27% |
Reaction Steps
A solution of 5-fluoro-1,3-dihydro-indol-2-one (70 mg, 0.46 mmol) in THF (0.6 mL) is placed under an Argon atmosphere and cooled in an ice bath. A solution of lithium bis(trimethylsilyl)amide (1.2 mL of a 1.0 M solution in THF, 1.2 mmol) is added slowly at 0° C. and the resulting solution is stirred for 10 min. The ice-bath is then removed and a solution of 2-(2-morpholin-4-yl-ethyl)-7H-furo[3,4-b]pyridin-5-one (80 mg, 0.32 mmol) in THF (2 mL) and added dropwise to the reaction mixture. The resulting solution is stirred for 4 h and then poured into an aqueous 10% HCl solution (40 mL). The resulting suspension is stirred at room temperature for 48 h. The yellow solid which precipitated from solution is collected by filtration and washed with 10% HCl, MeOH (3×5 mL) and Et2O (3×5 mL), and dried under vacuum overnight to give the title compound (33 mg, 27%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08455535B2 |
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| Source dataset | uspto-grants-2013_06 |
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| ORD ID | ord-8b3f069dd61243c08f8c4f8c6994a7f2 |
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| Source note | uspto-grants-2013_06 |
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