Sodium Carbonate → HCID 67496554, compound

HRID 1628325Notes

Reaction equation

HRID 1628325 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:14]=[C:15]([N+:17]([O-:19])=[O:18])[CH:16]=1)[CH2:5][N:6]1[CH2:9][CH:8]([C:10]([O:12][CH3:13])=[O:11])[CH2:7]1.[CH3:20][C:21]1[CH:26]=[C:25](B(O)O)[CH:24]=[CH:23][N:22]=1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:20][C:21]1[CH:26]=[C:25]([C:2]2[CH:3]=[C:4]([CH:14]=[C:15]([N+:17]([O-:19])=[O:18])[CH:16]=2)[CH2:5][N:6]2[CH2:9][CH:8]([C:10]([O:12][CH3:13])=[O:11])[CH2:7]2)[CH:24]=[CH:23][N:22]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 41926642-Methylpyridine-4-boronic acidHCID 67497160HCID 67497160, compound

Product 1

HCID 67496554HCID 67496554, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a rt solution of 79.D (2.42 g, 7.4 mmol) and 2-methylpyridin-4-ylboronic acid (available from CombiPhos Catalysts, Inc.) (2.52 g, 18.4 mmol) in DMF (22 mL) was added saturated aqueous Na2CO3 (5 mL) followed by bis(triphenylphosphine)palladium(ii) chloride (265 mg, 0.37 mmol) After being purged with N2 for 15 mins, the mixture was stirred at 50° C. under N2 atmosphere for 3.5 hrs. The reaction solution was cooled, diluted with water (35 mL), treated with acetic acid to pH=7, and extracted with EtOAc (3×30 mL). The combined organic layers were washed with water, brine dried over MgSO4, and filtered. After removal of organic solvent under reduced pressure, purification of the residue by flash chromatography on silica gel using 0-6% MeOH/CH2Cl2 for elution gave the title product 79.E as pale yellow solid (1.51 g, 60%).

Workup

  1. customAfter being purged with N2 for 15 mins
  2. temperatureThe reaction solution was cooled
  3. additiondiluted with water (35 mL)
  4. additiontreated with acetic acid to pH=7
  5. extractionextracted with EtOAc (3×30 mL)
  6. washThe combined organic layers were washed with water, brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customAfter removal of organic solvent
  10. customunder reduced pressure, purification of the residue by flash chromatography on silica gel using 0-6% MeOH/CH2Cl2
  11. washfor elution

Sources & evidence

ORD record
ord-ead8b2e5b01841cb81a5fda4bf18da2c
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

Loading…