Water → Methyl 2,6-dichloro-4-cyanonicotinate

HRID 515973

Reaction equation

HRID 515973 reaction equation
[Cl:1][C:2]1[N:11]=[C:10]([Cl:12])[CH:9]=[C:8](I)[C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:14]([Zn]C#N)#[N:15].O.CCOC(C)=O>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[N:11]=[C:10]([Cl:12])[CH:9]=[C:8]([C:14]#[N:15])[C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 58317523Methyl 2,6-dichloro-4-iodonicotinateHCID 178514179HCID 178514179, compound

Product 1

HCID 58317683Methyl 2,6-dichloro-4-cyanonicotinateYield 40.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of tetrakis(triphenylphosphine)palladium (34.8 mg, 0.03 mmol), methyl 2,6-dichloro-4-iodonicotinate (100 mg, 0.301 mmol) and dicyanozinc (38.9 mg, 0.331 mmol) in DMF (2 mL) was stirred at 100° C. overnight under N2 atmosphere. To the resulting mixture were added H2O and EtOAc. The aqueous phase was extracted with EtOAc, and the combined organic layers were washed with H2O and brine, dried over MgSO4 and evaporated. The residue was purified by chromatography on SiO2 to give the title compound as a white solid (28 mg, 40%). 1H NMR (500 MHz, DMSO-d6) δ ppm 3.99 (s, 3 H), 8.44 (s, 1H).

Workup

  1. extractionThe aqueous phase was extracted with EtOAc
  2. washthe combined organic layers were washed with H2O and brine
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customThe residue was purified by chromatography on SiO2

Sources & evidence

ORD record
ord-44060070b766493ba939af1aec8ea3f2
Source dataset
uspto-grants-2015_08
Patent number
US09108970B2

Linked notes

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