Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Pyrrolidine | HCID 31268 | — |
| Reactant | Oxalyl chloride | HCID 65578 | — |
| Reactant | HCID 59747887 | HCID 59747887 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 9913574 | HCID 9913574 | — |
Reaction Steps
[4-(4-Fluoro-benzyl)-piperidin-1-yl]-(6-methoxy-1H-pyrrolo[2,3-b]pyridin-5-yl)-methanone (368 mg, 1 mmol) was dissolved in dry dichloromethane (5 mL). It was cooled in an ice-bath and oxalyl chloride (4.5 mL, 2 M solution in dichloromethane) was added. The mixture was stirred for 1 h at 0° C. and for another 4 h at room temperature. It was evaporated to dryness, redissolved in dichloromethane and treated with pyrrolidine (3 mmol). After stirring for 30 min, water was added and the product was extracted with dichloromethane (3×25 mL). The combined extracts were dried over sodium sulfate. After evaporation of the solvent, the product was purified via radial chromatography using chloroform-methanol (0-3% methanol) to yield 340 mg of the desired product. LCMS: 493, M+1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07393851B2 |
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| Source dataset | uspto-grants-2008_07 |
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| ORD ID | ord-2eb497728eb540acb3926923f60bbf7b |
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| Source note | uspto-grants-2008_07 |
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