Water → HCID 69020065, compound

HRID 1865119Notes

Reaction equation

HRID 1865119 reaction equation
O.C(=O)([O-])[O-].[K+].[K+].[C:8]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:13]=[CH:12][C:11](B(O)O)=[CH:10][CH:9]=1.[CH2:23]([O:25][C:26]([C:28]1[N:29]([CH3:38])[C:30]([CH2:36][CH3:37])=[C:31]([C:34]#[N:35])[C:32]=1I)=[O:27])[CH3:24]>[Pd].C(O)C>[CH2:23]([O:25][C:26]([C:28]1[N:29]([CH3:38])[C:30]([CH2:36][CH3:37])=[C:31]([C:34]#[N:35])[C:32]=1[C:11]1[CH:12]=[CH:13][C:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:9][CH:10]=1)=[O:27])[CH3:24]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1512531,1'-Biphenyl-4-yl-boronic acidHCID 57975348HCID 57975348, compound

Product 1

HCID 69020065HCID 69020065, compoundYield 88.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Conditions

Temperature
80 °C

Procedure

Charge deionized water (0.50 L), potassium carbonate (66.3 grams, 0.48 mol), and 4-biphenyl boronic acid (62.4 grams, 0.315 mol) and ethanol (1.4 L) to a 3 L 3-neck reaction flask equipped with a mechanical stirrer, condenser, heating mantle, thermocouple, and nitrogen inlet. Stir the mixture to dissolve the solids. Add 4-cyano-5-ethyl-3-iodo-1-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (Preparation 38), additional ethanol (0.90 L) and stir the mixture while the flask is inerted with nitrogen. Add palladium black to the reaction mixture and heat the mixture to reflux at 80° C. Stir the reaction mixture at reflux for 70 minutes. Add ethyl acetate (0.50 L) and filter the mixture through Whatman® GF/F to remove palladium black. Concentrate the filtrate to about 0.6 L by distillation and filter the resulting suspension to collect the precipitate. Rinse the filter cake with ethanol (0.441 L) and vacuum-dry to afford 95.6 grams of the title compound in 88.7% yield.

Workup

  1. additionCharge
  2. customequipped with a mechanical stirrer, condenser
  3. temperatureheating mantle
  4. dissolutionto dissolve the solids
  5. stirringStir the reaction mixture
  6. temperatureat reflux for 70 minutes
  7. filtrationAdd ethyl acetate (0.50 L) and filter the mixture through Whatman® GF/F
  8. customto remove palladium black
  9. concentrationConcentrate the filtrate to about 0.6 L
  10. distillationby distillation
  11. filtrationfilter the resulting suspension
  12. customto collect the precipitate
  13. washRinse the filter cake with ethanol (0.441 L)
  14. customvacuum-dry

Sources & evidence

ORD record
ord-2529fcb1f59148ae8a4a64ea6739d733
Source dataset
uspto-grants-2009_12
Patent number
US07625932B2

Reaction notes

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