Potassium Carbonate → Methyl 3-cyano-5-cyclopropyl-4-methoxybenzoate

HRID 385059Notes

Reaction equation

HRID 385059 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11](I)[C:12]=1[OH:13])[C:6]([O:8][CH3:9])=[O:7])#[N:2].[C:15](=O)([O-])[O-].[K+].[K+].[CH:21]1(B(O)O)[CH2:23][CH2:22]1>O1CCOCC1.C(C1C=CC=C(C(C)C)C=1N1C=CN(C2C(C(C)C)=CC=CC=2C(C)C)C1=[Pd](Cl)(Cl)C1C(Cl)=CC=CN=1)(C)C>[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([CH:21]2[CH2:23][CH2:22]2)[C:12]=1[O:13][CH3:15])[C:6]([O:8][CH3:9])=[O:7])#[N:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2760897Cyclopropylboronic acidHCID 68108667HCID 68108667, compound

Product 1

HCID 68108310Methyl 3-cyano-5-cyclopropyl-4-methoxybenzoateYield 45.6%

Reagents, catalysts & solvents 2

HCID 178439031HCID 178439031, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

Methyl 3-cyano-4-hydroxy-5-iodobenzoate (1.00 g) was dissolved in 1,4-dioxane (15 mL), and potassium carbonate (1.31 g), cyclopropylboronic acid (325 mg) and [1,3-bis-(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium dichloride (108 mg) were added to the solution, and then the mixture was stirred under an argon gas flow at 95° C. for 22 hours. The reaction solution was filtered and the solvent was distilled off under reduced pressure, and then the obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1) to obtain the title compound (348 mg) as a pale yellow crystal.

Workup

  1. filtrationThe reaction solution was filtered
  2. distillationthe solvent was distilled off under reduced pressure
  3. customthe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-f74800f8786946b2b8caaff0623fd48b
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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