HuagongsheHuagongshe Chemistry Print Report · For research reference only
HCID 67406794, compound → HCID 67406460, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | HCID 67406794 | HCID 67406794 | — |
| Reactant | HCID 86675488 | HCID 86675488 | — |
| Catalyst | Zinc cyanide (Zn(CN)2) | HCID 11186 | — |
| Catalyst | Zinc | HCID 23994 | — |
| Catalyst | Ferrocene-1,1'-bis-(diphenylphosphine) | HCID 635956 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | HCID 67406460 | HCID 67406460 | 39% |
Reaction Steps
To the above mixture of 2-(biphenyl-3-yl)-3-bromo-5,6-dimethoxypyridine and 3-(biphenyl-3-yl)-2-bromo-5,6-dimethoxypyridine (50 mg, 0.135 mmol) were added, under argon, Zn(CN)2 (32 mg, 0.27 mmol), Zn powder (0.9 mg, 0.014 mmol), Pd2(dba)3 (12.4 mg, 0.014 mmol), DPPF (15 mg, 0.027 mmol), DMA (2 mL) and stirred at 120° C. for 3.5 h. Cooled to room temperature and filtered. Purification by preparative HPLC (10->85% CH3CN/H2O over 20 min, 0.05% added TFA) afforded 17 mg (39%) of 2-(biphenyl-3-yl)-5,6-dimethoxypyridine-3-carbonitrile as a tan solid. LC/MS (M+H)+ 317.2.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09309199B2 |
| Source dataset | uspto-grants-2016_04 |
| ORD ID | ord-1508e887c46a4f24963ab4b446242ff2 |
| Source note | uspto-grants-2016_04 |