ChemicalBook CAS DataBase List 2,6-Dichloro-5-cyclopropylnicotinonitrile

2,6-Dichloro-5-cyclopropylnicotinonitrile synthesis

3synthesis methods

Product Name:2,6-Dichloro-5-cyclopropylnicotinonitrile
CAS Number:1319804-29-9
Molecular formula:C9H6Cl2N2
Molecular Weight:213.06

1353087-61-2 Synthesis

1353087-61-2
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411235-57-9 Synthesis

411235-57-9
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2,6-Dichloro-5-cyclopropylnicotinonitrile

1319804-29-9
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Yield:1319804-29-9 70%

Reaction Conditions:

palladium diacetate;tricyclohexylphosphine in water;toluene;Reflux;Suzuki Coupling;

Steps:

9

[0539] A mixture of compound 2,6-dichloro-5-iodonicotinonitrile (10 g, 33.4 mmol), cyclopropylboronic acid (3.5 g, 40.1 mmol), K₃PO₄ (28 g, 133.6 mmol), Cy₃P (1 g, 3.3 mmol) and Pd(OAc)₂ (0.5 g, 2.2 mmol) in Toluene/H₂0 (300 mL/15 mL) was stirred under refluxing overnight. The mixture was poured into water and extracted with EtOAc. The separated organics was dried, concentrated and purified by column chromatography (Petroleum ether :EtO Ac = 10: 1) to give compound 2,6- dichloro-5-cyclopropylnicotinonitrile (5 g, 70%). 1H-NMR (400MHz, CDC1₃) δ (ppm) 7.43 (s, 1H), 2.08 (m, 1H), 1.18 (m, 2H), 0.69 (m, 2H)

References:

WO2011/94450,2011,A1 Location in patent:Page/Page column 158

3-Pyridinecarboxamide, 1,2-dihydro-6-hydroxy-5-iodo-2-oxo-

1319804-28-8
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1319804-29-9
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References

35441-11-3
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1319804-29-9
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References