Potassium Carbonate → HCID 178497370, compound

HRID 1488093Notes

Reaction equation

HRID 1488093 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1[NH:11][C:12](I)=[C:13]([C:15]([F:18])([F:17])[F:16])[N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20][C:21]1[CH:30]=[C:29]([CH3:31])[C:28](B2OC(C)(C)C(C)(C)O2)=[CH:27][C:22]=1[C:23]([O:25][CH3:26])=[O:24].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]>[CH2:1]([O:8][CH2:9][C:10]1[NH:11][C:12]([C:28]2[C:29]([CH3:31])=[CH:30][C:21]([CH3:20])=[C:22]([CH:27]=2)[C:23]([O:25][CH3:26])=[O:24])=[C:13]([C:15]([F:18])([F:17])[F:16])[N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

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 178506276HCID 178506276, compound2×

Product 1

HCID 178497370HCID 178497370, compoundYield 37%

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 50-mL three neck round-bottom flask, which was purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 2-((benzyloxy)methyl)-5-iodo-4-(trifluoromethyl)-1H-imidazole (compound 219.2, 500 mg, 1.31 mmol) in dioxane (8 mL). Methyl 2,4-dimethyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (compound 160.1, 450 mg, 1.55 mmol), Pd(dppf)Cl2 (0.1 g) and an aqueous solution of potassium carbonate (2 M) (3.25 mL) were added to the reaction. The reaction mixture was stirred for 1 h at 80° C., then diluted with 20 mL of H2O. The aqueous phase was extracted with 2×30 mL of ethyl acetate. The combined organic layers were washed with 2×30 mL of brine and dried over anhydrous sodium sulfate. The residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1/20-1/4) as eluent to yield 0.2 g (37%) of the title compound as a light yellow solid.

Workup

  1. customInto a 50-mL three neck round-bottom flask, which was purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. extractionThe aqueous phase was extracted with 2×30 mL of ethyl acetate
  4. washThe combined organic layers were washed with 2×30 mL of brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1/20-1/4) as eluent

Sources & evidence

ORD record
ord-5736413c66044ec7b95bbebc0dbf7b7c
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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