HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl Acetate → Benzyl 3-(6-{3-[(tert-butoxycarbonyl)amino]prop-1-ynyl}pyridin-3-yl)prop-2-ynylcarbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 2,5-Dibromopyridine | HCID 69353 | — |
| Reactant | tert-butyl N-(prop-2-yn-1-yl)carbamate | HCID 11073648 | — |
| Reactant | Benzyl prop-2-yn-1-ylcarbamate | HCID 11137906 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Diisopropylamine | HCID 7912 | — |
| Product | Benzyl 3-(6-{3-[(tert-butoxycarbonyl)amino]prop-1-ynyl}pyridin-3-yl)prop-2-ynylcarbamate | HCID 21299383 | 11.9% |
Reaction Steps
A mixture of 2,5-dibromopyridine (1.19 g), N-Boc-propargylamine (781 mg), Pd(PPh3)2Cl2 (73 mg), and CuI (10 mg) in diisopropylamine (20 mL) was stirred at room temperature overnight under nitrogen atmosphere. To the mixture was added N-Cbz-propargylamine (1.14 g) and the mixture was heated under reflux temperature for 5 hours under nitrogen atmosphere. The mixture was cooled to room temperature. To the mixture was added ethyl acetate (50 mL). The precipitates were filtered and washed with ethyl acetate. The filtrate and washings were combined and purified by silica gel column to give 6-1 (250 mg) as a crystalline compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06706885B2 |
| Source dataset | uspto-grants-2004_03 |
| ORD ID | ord-23e7eb85123f438d84ad90e4f736190c |
| Source note | uspto-grants-2004_03 |