Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | HCID 57860971 | HCID 57860971 | — |
| Catalyst | Zinc cyanide (Zn(CN)2) | HCID 11186 | — |
| Catalyst | Tetrakis(triphenylphosphine)palladium | HCID 11979704 | — |
| Product | HCID 68630708 | HCID 68630708 | 32% |
Reaction Steps
A mixture of (R)-indan-1-yl-(6-bromo-quinolin-2-yl)-amine (1.14 g, 3.36 mmol), zinc cyanide (434 mg, 3.7 mmol) and tetrakis-(triphenylphosphine)-palladium (388 mg, 0.34 mmol) in DMF (12 ml) was heated at 160° C. for 15 min in a microwave reactor. The reaction mixture was poured into water (100 ml) and extracted with ethyl acetate (3×100 ml). The combined organic layers were washed with brine (2×50 ml), dried (MgSO4) and evaporated. The crude product was purified by flash chromatography (ethyl acetate/heptane) on silica gel and crystallization (diethyl ether/heptane) to yield 2-((R)-indan-1-ylamino)-quinoline-6-carbonitrile as light yellow solid (310 mg, 32%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08188284B2 |
|---|
| Source dataset | uspto-grants-2012_05 |
|---|
| ORD ID | ord-f76e5fa4f0c84972af31069659f86cc0 |
|---|
| Source note | uspto-grants-2012_05 |
|---|