HuagongsheHuagongshe Chemistry Print Report · For research reference only
Phenylacetylene → 5-Nitro-3-(phenylethynyl)pyridin-2-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Phenylacetylene | HCID 10821 | — |
| Reactant | 2-Amino-3-bromo-5-nitropyridine | HCID 2734412 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Product | 5-Nitro-3-(phenylethynyl)pyridin-2-amine | HCID 59322901 | 50% |
Reaction Steps
A solution of 3-bromo-5-nitropyridin-2-amine (655 mg, 3.0 mmol, 1.0 eq.) in 1:1 TEA/DMF (40 mL) was degassed with argon for 10 minutes, and ethynylbenzene (1.5 eq.), CuI (0.04 eq.), and PdCl2(PPh3)2 (0.04 eq.) were sequentially added. The mixture was degassed with argon for 10 minutes, and then stirred at room temperature for 16 hours. The volatiles were removed under reduced pressure, and CH2Cl2 (25 mL) was added. The mixture was sonicated for 15 minutes, cooled to 0° C., and collected by vacuum filtration to afford 5-nitro-3-(phenylethynyl)pyridin-2-amine (356 mg, 50%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08338452B2 |
| Source dataset | uspto-grants-2012_12 |
| ORD ID | ord-59cf437319694310ba6ab629fde7002c |
| Source note | uspto-grants-2012_12 |