Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 1-Iodopropane | HCID 33643 | — |
| Reactant | tert-Butyl 2-chloro-5-iodopyridin-4-ylcarbamate | HCID 72206934 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Solvent | Sodium hydride | HCID 24758 | — |
| Product | HCID 90051681 | HCID 90051681 | — |
Reaction Steps
To a solution of tert-butyl (2-chloro-5-iodopyridin-4-yl)carbamate (S8, 239 mg) and propyl iodide (131 μL) in N-methylpyrrolidone (3 mL), sodium hydride (60% wt, 80 mg) was added under ice cooling, and the mixture was stirred at room temperature for 2 hours, and then stirred at 50° C. for 3 hours. The reaction mixture was cooled to room temperature, and then ethyl acetate and water were added to the reaction mixture. The organic layer was separated, washed with saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel chromatography (eluent, 100 to 70% hexane in ethyl acetate) to obtain tert-butyl (2-chloro-5-iodopyridin-4-yl)(propyl)carbamate (S9, 155 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09145415B2 |
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| Source dataset | uspto-grants-2015_09 |
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| ORD ID | ord-bffba2d216604710a6c507cfcdecafa3 |
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| Source note | uspto-grants-2015_09 |
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