Potassium Carbonate → HCID 178497364, compound

HRID 1488123Notes

Reaction equation

HRID 1488123 reaction equation
I[C:2]1[NH:6][C:5]([CH3:7])=[N:4][C:3]=1[CH:8]=[O:9].[CH3:10][C:11]1[CH:20]=[C:19]([CH3:21])[C:18](B2OC(C)(C)C(C)(C)O2)=[CH:17][C:12]=1[C:13]([O:15][CH3:16])=[O:14].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.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]>[CH:8]([C:3]1[N:4]=[C:5]([CH3:7])[NH:6][C:2]=1[C:18]1[C:19]([CH3:21])=[CH:20][C:11]([CH3:10])=[C:12]([CH:17]=1)[C:13]([O:15][CH3:16])=[O:14])=[O:9]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 59224686Methyl 2,4-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate2×HCID 90029530HCID 90029530, compound2×

Product 1

HCID 178497364HCID 178497364, compoundYield 58%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

Into a 100-mL three neck round-bottom flask, which was purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 5-iodo-2-methyl-1H-imidazole-4-carbaldehyde (compound 236.1, 600 mg, 2.54 mmol) in dioxane (30 mL). Methyl 2,4-dimethyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (compound 160.1, 800 mg, 2.76 mmol), a solution of potassium carbonate (1.8 g, 13.0 mmol) in water (10 mL), and Pd(dppf)Cl2 (400 mg, 0.55 mmol, 0.20 equiv) were added to the reaction. The reaction mixture was stirred for overnight at 80° C., then was quenched with 20 mL of water. The aqueous phase was extracted with 2×100 mL of ethyl acetate and the combined organic layers were washed with 2×50 mL of brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (3:1) as eluent to furnish 400 mg (58%) of the title compound as a light yellow solid.

Workup

  1. customInto a 100-mL three neck round-bottom flask, which was purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. customwas quenched with 20 mL of water
  4. extractionThe aqueous phase was extracted with 2×100 mL of ethyl acetate
  5. washthe combined organic layers were washed with 2×50 mL of brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (3:1) as eluent

Sources & evidence

ORD record
ord-4db4d32f275846b59d948424eac7f4d3
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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