Potassium Carbonate → HCID 67267387, compound

HRID 602521Notes

Reaction equation

HRID 602521 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[NH:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][CH2:13][C:14]2[S:15][C:16]([Cl:19])=[CH:17][CH:18]=2)=[CH:8][C:7]=1I)[CH3:2].[N:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[C:24](B(O)O)[CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC(C)=O>[CH2:1]([O:3][C:4](=[O:21])[NH:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][CH2:13][C:14]2[S:15][C:16]([Cl:19])=[CH:17][CH:18]=2)=[CH:8][C:7]=1[C:24]1[CH:23]=[N:22][C:31]2[C:26]([CH:25]=1)=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2734663Quinoline-3-boronic acidHCID 67267453HCID 67267453, compound

Product 1

HCID 67267387HCID 67267387, compoundYield 33.2%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 180AcetoneSolvent

Conditions

Temperature
125 °C

Procedure

{4-[(5-Chloro-thiophen-2-ylmethyl)-amino]-2-iodophenyl}-carbamic acid ethyl ester (15 mg), 3-quinolineboronic acid (29.7 mg), palladium(II) acetate (ca. 1 mg), potassium carbonate (0.035 mL, 5M aqueous solution), and acetone (2 mL) were mixed and heated in heated in a sealed glass tube in a microwave synthesizer for 10 minutes at 125° C. After cooling to room temperature, the reaction mixture was extracted with ethyl acetate (4 mL), the organic phase washed with water (2×2 mL), and brine (2×2 mL), dried over magnesium sulfate, and filtered. The solvent was removed in vacuo, and the crude product was purified by preparative LC-MS. The collected fraction was evaporated in: vacuo, redissolved in ethyl acetate (5 mL), and the organic phase was washed with saturated aqueous sodium bicarbonate (3 mL), water (3 mL), and brine (2×2 mL). The organic phase was dried over magnesium sulfate, filtered, and the solvent was removed in vacuo to furnish the title compound (5 mg, 33%).

Workup

  1. temperatureheated
  2. temperatureAfter cooling to room temperature
  3. extractionthe reaction mixture was extracted with ethyl acetate (4 mL)
  4. washthe organic phase washed with water (2×2 mL), and brine (2×2 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customThe solvent was removed in vacuo
  8. customthe crude product was purified by preparative LC-MS
  9. customThe collected fraction was evaporated in: vacuo
  10. dissolutionredissolved in ethyl acetate (5 mL)
  11. washthe organic phase was washed with saturated aqueous sodium bicarbonate (3 mL), water (3 mL), and brine (2×2 mL)
  12. dry with materialThe organic phase was dried over magnesium sulfate
  13. filtrationfiltered
  14. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-bda9e553c766473b8c3c8f4acaddc944
Source dataset
uspto-grants-2011_03
Patent number
US07906537B2

Reaction notes

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