Sodium Carbonate → HCID 58587745, compound

HRID 1361707Notes

Reaction equation

HRID 1361707 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][CH:32]=1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[C:20]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([NH:27][CH3:28])[N:22]=3)=[CH:19][CH:18]=[CH:17][N:16]=2)=[C:10]([CH3:29])[CH:9]=1)=[O:6].[O:33]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34]1.C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>O.C(OCC)(=O)C>[O:33]1[CH:37]=[CH:36][C:35]([C:2]2[CH:3]=[C:4]([CH:30]=[CH:31][CH:32]=2)[C:5]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]3[C:20]([C:21]4[CH:26]=[CH:25][N:24]=[C:23]([NH:27][CH3:28])[N:22]=4)=[CH:19][CH:18]=[CH:17][N:16]=3)=[C:10]([CH3:29])[CH:9]=2)=[O:6])=[CH:34]1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 2734358Furan-3-boronic acidHCID 66970357HCID 66970357, compound

Product 1

HCID 58587745HCID 58587745, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-iodo-N-(3-methyl-4-(3-(2-(methylamino)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)benzamide (0.100 g, 0.186 mmol), furan-3-ylboronic acid (0.025 g, 0.22 mmol), [1,1′bis(diphenylphosphino)ferrocene] palladium(II) methylene chloride complex (0.0073 g, 0.01 mmol), sodium carbonate (2M solution in water, 0.20 mL, 0.41 mmol) and dioxane was heated to 80 deg. C. for 3 h. The reaction was cooled to ambient temperature and was allowed to stand overnight. Additional [1,1′bis(diphenylphosphino)ferrocene]palladium(II) methylene chloride complex (0.0073 g, 0.01 mmol) was added and the reaction was heated to 85 deg. C. for 3 hr. The reaction was cooled to ambient temperature and was diluted with water and ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The material was further purified by reverse-phase HPLC using acetonitrile/water/TFA as eluent to give 3-(furan-3-yl)-N-(3-methyl-4-(3-(2-(methylamino)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)benzamide. MS m/z=478 [M+1]+. Calc'd for C28H23N5O3: 477.52.

Workup

  1. temperaturewas heated to 80 deg. C
  2. waitto stand overnight
  3. additionAdditional [1,1′bis(diphenylphosphino)ferrocene]palladium(II) methylene chloride complex (0.0073 g, 0.01 mmol) was added
  4. temperaturethe reaction was heated to 85 deg. C
  5. waitfor 3 hr
  6. temperatureThe reaction was cooled to ambient temperature
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe material was further purified by reverse-phase

Sources & evidence

ORD record
ord-8b335447df874346a432ba64fc5eb639
Source dataset
uspto-grants-2011_02
Patent number
US07880000B2

Reaction notes

Loading…