Sodium Carbonate → HCID 69067909, compound

HRID 733136Notes

Reaction equation

HRID 733136 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13](Br)[CH:12]=2)[CH:10]=1)=[O:5])[CH3:2].[Cl:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C(O)CC.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([N:9]2[CH:10]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:7]=[N:8]2)[CH:12]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 27343222-Chlorophenylboronic acidHCID 53419315HCID 53419315, compound

Product 1

HCID 69067909HCID 69067909, compoundYield 79%

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 10311-PropanolSolvent

Procedure

To a solution of the product from Step 2 (0.477 g, 1.6 mmol) in n-propanol (2.76 mL) and water (0.56 mL) were added 2-chlorophenylboronic acid (0.328 g, 2.1 mmol), palladium acetate (0.001 g, 0.3 mol %), triphenylphosphine (0.004 g, 0.9 mol %) and 2M sodium carbonate (0.96 mL, 1.9 mmol), and the reaction was refluxed for 16 hours. The reaction mixture was cooled and partitioned between EtOAc and water. The organic phase was washed with saturated sodium bicarbonate, brine and dried over sodium sulfate. It was then filtered, concentrated and purified by chromatography using 20% EtOAc in hexanes to yield 0.412 g of the product (79%).

Workup

  1. temperaturethe reaction was refluxed for 16 hours
  2. temperatureThe reaction mixture was cooled
  3. custompartitioned between EtOAc and water
  4. washThe organic phase was washed with saturated sodium bicarbonate, brine
  5. dry with materialdried over sodium sulfate
  6. filtrationIt was then filtered
  7. concentrationconcentrated
  8. custompurified by chromatography

Sources & evidence

ORD record
ord-411e53d2001a4aa5bba54f93f2bf5a5a
Source dataset
uspto-grants-2009_09
Patent number
US07589116B2

Reaction notes

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