Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Cyanide | HCID 5975 | — |
| Reactant | HCID 67095932 | HCID 67095932 | — |
| Catalyst | Tetrakis(triphenylphosphine)palladium | HCID 11979704 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 67096021 | HCID 67096021 | 79% |
Reaction Steps
A mixture of (R)-indan-1-yl-(5-iodo-quinolin-2-yl)-amine (example 6, step A) (1.44 g, 3.73 mmol), zink cyanide (482 mg, 4.1 mmol) and tetrakis-(triphenylphosphine)-palladium (431 mg, 0.37 mmol) in DMF (20 ml) was heated at 160° C. for 15 min in a microwave reactor. The reaction mixture was poured into water (50 ml) and extracted with ethyl acetate (2×100 ml). The combined organic layers were washed with brine (50 ml), dried (MgSO4) and evaporated. The crude product was purified by flash chromatography (ethyl acetate/heptane) on silica gel and crystallization (diethyl ether/hexane) to yield 2-((R)-indan-1-ylamino)-quinoline-5-carbonitrile as light yellow solid (840 mg, 79%). M.p. 150° C.; MS: m/e=286.2 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07923561B2 |
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| Source dataset | uspto-grants-2011_04 |
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| ORD ID | ord-3d4561efcf314c23b98dfe9e865b5280 |
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| Source note | uspto-grants-2011_04 |
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