Potassium Carbonate → HCID 58020263, compound

HRID 1632090Notes

Reaction equation

HRID 1632090 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([O:12][CH3:13])=[C:7](B(O)O)[CH:8]=1)=[O:2].Br[C:15]1[CH:25]=[CH:24][C:18]2[O:19][C:20]([F:23])([F:22])[O:21][C:17]=2[CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>O.CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:23][C:20]1([F:22])[O:19][C:18]2[CH:24]=[CH:25][C:15]([C:7]3[CH:8]=[C:3]([CH:4]=[CH:5][C:6]=3[O:12][CH3:13])[CH:1]=[O:2])=[CH:16][C:17]=2[O:21]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27343675-Formyl-2-methoxyphenylboronic acidHCID 27362715-Bromo-2,2-difluoro-1,3-benzodioxole

Product 1

HCID 58020263HCID 58020263, compoundYield 39%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of 5-formyl-2-methoxy phenyl boronic acid (1.0 g, 5.5 mmol) in water (6 mL) and methanol (30 mL), was added 5-bromo-2,2-difluoro-1,3-benzodioxole (0.97 mL, 7.2 mmol), solid potassium carbonate (1.5 g, 11 mmol), and palladium(II) acetate (25 mg, 0.11 mmol). The reaction was stirred at room temperature for 16 h. The black mixture was diluted with water (30 mL) and extracted with ethyl acetate (2×30 mL). The combined extracts were decolorized with activated charcoal, dried over sodium sulfate, filtered, and concentrated to 20 mL under vacuum. The solution was purified by silica gel column chromatography eluting with hexanes/ethyl acetate (11:1) to give I-172 (620 mg, 39% yield) as a white solid.

Workup

  1. extractionextracted with ethyl acetate (2×30 mL)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to 20 mL under vacuum
  5. customThe solution was purified by silica gel column chromatography
  6. washeluting with hexanes/ethyl acetate (11:1)
  7. customto give I-172 (620 mg, 39% yield) as a white solid

Sources & evidence

ORD record
ord-61d9c6459f7f4f1595f2d2f825b507a7
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Reaction notes

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