HuagongsheHuagongshe Chemistry Print Report · For research reference only
2,5-Dibromopyridine → N-[3-(5-Bromopyridin-2-yl)prop-2-ynyl]acetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2,5-Dibromopyridine | HCID 69353 | — |
| Reactant | 65881-41-6 | HCID 240796 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Diisopropylamine | HCID 7912 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | N-[3-(5-Bromopyridin-2-yl)prop-2-ynyl]acetamide | HCID 12991110 | 89.7% |
Reaction Steps
A mixture of 2,5-dibromopyridine (1-1) (1.19 g), N-acetyl-propargylamine (733 mg), CuI (10 mg), and Pd(PPh3)2Cl2 (73 mg) in diisopropylamine (20 mL) was stirred at ambient temperature under nitrogen atmosphere over 3 days. The mixture was diluted with ethyl acetate (50 mL). The solid was filtered and washed with ethyl acetate. The filtrate and wash were combined and concentrated under reduced pressure. The residue was purified by silica gel column chromatography using ethyl acetate as eluant to give crystalline 1-2 (1.14 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06706885B2 |
| Source dataset | uspto-grants-2004_03 |
| ORD ID | ord-20010559d84d49ec8985a26d4a1dbf05 |
| Source note | uspto-grants-2004_03 |