HuagongsheHuagongshe Chemistry Print Report · For research reference only
(+-)-2-Butanol → Tert-butyl (1r)-3-(5-bromo-3-(2,2-dimethylcyclopropanecarboxamido)-1h-pyrrolo[2,3-b]pyridin-4-yl)cyclohexylcarbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | (+-)-2-Butanol | HCID 6568 | — |
| Reactant | (3R)-3-Aminopiperidine, 3-BOC protected | HCID 1514172 | — |
| Reactant | N-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-2,2-dimethylcyclopropanecarboxamide | HCID 60205714 | — |
| Product | Tert-butyl (1r)-3-(5-bromo-3-(2,2-dimethylcyclopropanecarboxamido)-1h-pyrrolo[2,3-b]pyridin-4-yl)cyclohexylcarbamate | HCID 60205715 | 46.5% |
Reaction Steps
N-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-2,2-dimethylcyclopropanecarboxamide (500 mg, 1.53 mmol) and (R)-tert-butyl piperidin-3-ylcarbamate (921 mg, 4.60 mmol) in s-BuOH (10 mL) were stirred at 130° C. for 18 hours. The reaction was concentrated and purified by reverse phase chromatography (SP4, 25M, water/ACN 90/10→0/100, 30 CV) to yield tert-butyl (1R)-3-(5-bromo-3-(2,2-dimethylcyclopropanecarboxamido)-1H-pyrrolo[2,3-b]pyridin-4-yl)cyclohexylcarbamate (360 mg, 46.5% yield) as a solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08545897B2 |
| Source dataset | uspto-grants-2013_10 |
| ORD ID | ord-879465d8fbfb494ab2c4ea80aa2bb71b |
| Source note | uspto-grants-2013_10 |