Potassium Carbonate → HCID 68288710, compound

HRID 541309Notes

Reaction equation

HRID 541309 reaction equation
Br[C:2]1[CH:11]=[C:10]([CH3:12])[C:9]([C:13]#[N:14])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH:15]1(B(O)O)[CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].CC([O-])=O.CC([O-])=O.[Pd+2]>[C:13]([C:9]1[C:10]([CH3:12])=[CH:11][C:2]([CH:15]2[CH2:17][CH2:16]2)=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5])#[N:14]

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 2760897Cyclopropylboronic acidHCID 68289087HCID 68289087, compound2×

Product 1

HCID 68288710HCID 68288710, compoundYield 98.2%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of methyl 2-bromo-5-cyano-4-methylbenzoate (compound 190.2, 600 mg, 2.13 mmol, 1.00 equiv, 90%) in toluene (20 mL) under nitrogen were added cyclopropylboronic acid (552 mg, 6.43 mmol, 2.00 equiv), a solution of potassium carbonate (876 mg, 6.34 mmol, 2.00 equiv) in water (1 mL), Pd(dppf)Cl2 (252 mg, 0.10 equiv), and Pd(OAc)2 (70 mg, 0.10 equiv). The resulting mixture was stirred under nitrogen at 100° C. overnight. After cooling to ambient temperature, the mixture was diluted with 20 mL of H2O, then extracted with 3×50 mL of ethyl acetate. The combined organic layers were dried (Na2SO4) and concentrated in vacuo to furnish 450 mg (89%) of methyl 5-cyano-2-cyclopropyl-4-methylbenzoate as a white solid.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. extractionextracted with 3×50 mL of ethyl acetate
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f7d86078ad1943918cdf19401f205b65
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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