HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1919072Generated: November 1, 2026
Sodium cyanoborohydride → 5-Bromo-1-methyl-3-(5-(1-(oxetan-3-yl)piperidin-4-yl)pyridin-2-ylamino)pyridin-2(1H)-one
https://huagongshe.com/reaction/1919072
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium cyanoborohydride | HCID 5003444 | — |
| Reactant | 3-Oxetanone | HCID 15024254 | — |
| Reactant | DCM ether MeOH | HCID 22565053 | — |
| Reactant | HCID 86661254 | HCID 86661254 | — |
| Catalyst | Zincchloride | HCID 3007855 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | 5-Bromo-1-methyl-3-(5-(1-(oxetan-3-yl)piperidin-4-yl)pyridin-2-ylamino)pyridin-2(1H)-one | HCID 86661255 | 30.5% |
Reaction Steps
Following Example 214b, 264b (450 mg, 1.25 mmol), oxetan-3-one (800 mg, 11.1 mmol) in methanol (10 mL) were mixed. Sodium cyanoborohydride (236 mg, 3.75 mmol) and zinc chloride (256 mg, 1.88 mmol) in methanol (10 mL) was added, and the reaction was heated at 48° C. for 12 hours. Work-up and flash column chromatography (silica, 60:35:5 methylene chloride/diethyl ether/methanol) afford a 30% yield (160 mg) of 264c as a light green solid: MS (ESI+) m/z 421.1 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08618107B2 |
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| Source dataset | uspto-grants-2013_12 |
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| ORD ID | ord-7f188b2bcc9f4a84aa8b1f11d54fcb52 |
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| Source note | uspto-grants-2013_12 |
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