Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | HCID 67334536 | HCID 67334536 | — |
| Catalyst | Zinc cyanide (Zn(CN)2) | HCID 11186 | — |
| Catalyst | Tetrakis(triphenylphosphine)palladium | HCID 11979704 | — |
| Product | HCID 67333492 | HCID 67333492 | 91% |
Reaction Steps
A stirred mixture of (5-iodo-quinolin-2-yl)-(5-methyl-furan-2-ylmethyl)-amine (example 50, step A) (500 mg, 1.37 mmol), zinc cyanide (177 mg, 1.5 mmol) and tetrakis-(triphenylphosphine)-palladium (159 mg, 0.14 mmol) in DMF (5 ml) was heated at 160° C. for 15 min in a microwave reactor. The reaction mixture was poured into water (15 ml) and extracted with ethyl acetate (2×10 ml). The combined organic layers were washed with brine (10 ml), dried (MgSO4) and evaporated. The crude product was purified by flash chromatography (ethyl acetate/heptane) on silica gel to yield 2-[(5-methyl-furan-2-ylmethyl)-amino]-quinoline-5-carbonitrile as light brown solid (346 mg, 91%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07825253B2 |
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| Source dataset | uspto-grants-2010_11 |
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| ORD ID | ord-8a2c8ab83be24ac39a1fefcc6537d6d8 |
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| Source note | uspto-grants-2010_11 |
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