Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | HCID 11173252 | HCID 11173252 | — |
| Catalyst | Zinc cyanide (Zn(CN)2) | HCID 11186 | — |
| Catalyst | Ferrocene-1,1'-bis-(diphenylphosphine) | HCID 635956 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Product | HCID 11299938 | HCID 11299938 | — |
Reaction Steps
A mixture of 1-chloro-4-(phenylmethoxy)isoquinoline (2.26 g, 8.4 mmol), Zn(CN)2 (590 mg), tris(dibenzylideneacetone)dipalladium (219 mg), 1,1′-bis(diphenylphosphino)ferrocene (270 mg) in 100 ml of DMF is heated at 150° C. for 24 h under nitrogen. TLC and LC-MS analysis indicates complete consumption of starting material after 24 h. The mixture is then cooled to 80° C. and gradually diluted with 4:1:4 saturated aq. NH4Cl: concentrated NH4OH:water (200 mL) over 0.5 hours. The slurry is cooled to 0° C. and filtered through celite. The tan solid is collected by filtration, washed and dried to give the titled compound as a tan solid (1.5 g), m.p. 124-125° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06528649B2 |
|---|
| Source dataset | uspto-grants-2003_03 |
|---|
| ORD ID | ord-3c6b529287bc49f8a79d705c0bbf5e93 |
|---|
| Source note | uspto-grants-2003_03 |
|---|
