Ethanol → 5-Propyl-1-(2'-sulfamoylbiphenyl-4-ylmethyl)-1H-pyrazole-3-carboxylic Acid Ethyl Ester

HRID 71660Notes

Reaction equation

HRID 71660 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([CH2:11][CH2:12][CH3:13])[N:8]([CH2:14][C:15]2[CH:20]=[CH:19][C:18](Br)=[CH:17][CH:16]=2)[N:7]=1)=[O:5])[CH3:2].C([NH:26][S:27]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1B1OC(C)(C)C(C)(C)O1)(=[O:29])=[O:28])(C)(C)C.C1(C)C=CC=CC=1.CCO.C(=O)([O-])[O-].[K+].[K+].C(O)(C(F)(F)F)=O>O.CCOC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([CH2:11][CH2:12][CH3:13])[N:8]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=3[S:27](=[O:29])(=[O:28])[NH2:26])=[CH:17][CH:16]=2)[N:7]=1)=[O:5])[CH3:2]

Participants

9

Reactant 6

HCID 702EthanolHCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 574695852-(tert-butylaMino)sulfonyl-phenylboronic acid pinacol esterHCID 667575461-(4-Bromobenzyl)-5-propyl-1H-pyrazole-3-carboxylic Acid Ethyl Ester

Product 1

HCID 667578145-Propyl-1-(2'-sulfamoylbiphenyl-4-ylmethyl)-1H-pyrazole-3-carboxylic Acid Ethyl Ester

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

1-(4-Bromobenzyl)-5-propyl-1H-pyrazole-3-carboxylic acid ethyl ester (1.2 g, 3.3 mmol) and N-t-butyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene sulfonamide (1.4 g, 4.0 mmol) were combined with toluene (70.9 mL, 666.0 mmol) and EtOH (18.5 mL, 316.7 mmol). Potassium carbonate (920 mg, 6.7 mmol) was dissolved in water (9.6 mL, 532.8 mmol) and added to the mixture, and stirred. Tetrakis(triphenyl-phosphine)palladium(0) (385 mg, 333 μmol) was added quickly and the mixture heated at 100° C. for 30 minutes in the microwave. EtOAc and water was added and organics were extracted and evaporated. The crude product was dissolved in neat TFA (20 mL, 300 mmol) and stirred at 50° C. for 1.5 hours. The product was dried under vacuum. DCM (20 mL) and saturated NaHCO3 (20 mL) were added, stirred and extracted, dried, and evaporated to yield the title compound.

Workup

  1. additionadded to the mixture
  2. extractionorganics were extracted
  3. customevaporated
  4. stirringstirred at 50° C. for 1.5 hours
  5. customThe product was dried under vacuum
  6. additionDCM (20 mL) and saturated NaHCO3 (20 mL) were added
  7. stirringstirred
  8. extractionextracted
  9. customdried
  10. customevaporated

Sources & evidence

ORD record
ord-9ee4b8ee958f4cc3a47798321ab2aa6f
Source dataset
uspto-grants-2014_09
Patent number
US08822522B2

Reaction notes

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