Tetrafluoroboric acid → HCID 67215702, compound

HRID 1627959Notes

Reaction equation

HRID 1627959 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:14])[N:11]([CH3:13])[CH3:12])[CH:6]=[CH:7][CH:8]=1.I[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1.[H+].[B-](F)(F)(F)F>CC([O-])=O.[Ag+].CC([O-])=O.CC([O-])=O.[Pd+2].O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[C:5]([NH:9][C:10](=[O:14])[N:11]([CH3:13])[CH3:12])[CH:4]=1

Participants

7

Reactant 3

HCID 28118Tetrafluoroboric acidHCID 34178Urea, 3-(m-methoxyphenyl)-1,1-dimethyl-HCID 696764-Iodoanisole

Product 1

HCID 67215702HCID 67215702, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 11246Silver acetateCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Procedure

3-(3-Methoxyphenyl)-1,1-dimethylurea (49 mg, 0.25 mmol), 1-iodo-4-methoxybenzene (117 mg, 0.50 mmol), AgOAc (0.5 mmol, 83 mg), and Pd(OAc)2 (0.025 mmol, 5.6 mg), were sequentially added under air to a reaction tube equipped with a stir bar and septum. An aliquot of TPGS-M-PEG-750/H2O (1.0 mL; 2.0% TPGS-M-PEG-750 by weight) solution, and 48 wt % aqueous HBF4 solution (1.25 mmol, 0.16 mL) were added by syringe and stirred vigorously for 24 h. After the reaction, the contents of the flask were quenched with NaHCO3 and extracted with EtOAc. The solution obtained was dried over anhydrous MgSO4 and concentrated by rotary evaporation. The residue was purified by flash chromatography eluting with 1:1 EtOAc/hexanes to afford the product (51 mg, 68%) as a white solid.

Workup

  1. customequipped with a stir bar
  2. customAfter the reaction
  3. customthe contents of the flask were quenched with NaHCO3
  4. extractionextracted with EtOAc
  5. customThe solution obtained
  6. dry with materialwas dried over anhydrous MgSO4
  7. concentrationconcentrated by rotary evaporation
  8. customThe residue was purified by flash chromatography
  9. washeluting with 1:1 EtOAc/hexanes

Sources & evidence

ORD record
ord-55318af2a336468abc83778d8b841645
Source dataset
uspto-grants-2014_07
Patent number
US08785665B2

Reaction notes

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