Hydrochloric Acid → HCID 25052029, compound

HRID 570837Notes

Reaction equation

HRID 570837 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]=[C:14](Br)[C:13]([C:17]#[N:18])=[N:12]2)=[CH:7][CH:6]=1)[CH3:2].[CH2:20]1[O:28][C:27]2[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][C:22]=2[O:21]1.C(=O)([O-])[O-].[Na+].[Na+].Cl>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN(C)C=O.O>[CH2:1]([O:3][C:4](=[O:19])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]=[C:14]([C:25]3[CH:24]=[CH:23][C:22]4[O:21][CH2:20][O:28][C:27]=4[CH:26]=3)[C:13]([C:17]#[N:18])=[N:12]2)=[CH:7][CH:6]=1)[CH3:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 2734371(2H-1,3-benzodioxol-5-yl)boronic acidHCID 25052028HCID 25052028, compound

Product 1

HCID 25052029HCID 25052029, compoundYield 26.1%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of 4-(4-bromo-3-cyanopyrazole-1-yl)benzoic acid ethyl ester (0.17 g), (3,4-methylenedioxyphenyl)boronic acid (0.11 g), tetrakis(triphenylphosphine) palladium (0.12 g) and sodium carbonate (0.17 g) in a mixed solvent of water (0.5 mL) and N,N-dimethylformamide (5 mL) was stirred at 70° C. for 12 hours. To this reaction mixture was added dilute hydrochloric acid, and this mixture was extracted with ethyl acetate. This organic layer was washed with brine, dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography on aminopropyl silica gel (eluent: ethyl acetate/n-hexane=1/5) to give the title compound (0.05 g).

Workup

  1. extractionthis mixture was extracted with ethyl acetate
  2. washThis organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customThe residue was purified by column chromatography on aminopropyl silica gel (eluent: ethyl acetate/n-hexane=1/5)

Sources & evidence

ORD record
ord-b8de735ddec04591afead0312456964c
Source dataset
uspto-grants-2015_05
Patent number
US09023882B2

Reaction notes

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