Potassium Carbonate → HCID 86668982, compound

HRID 1410158Notes

Reaction equation

HRID 1410158 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:13]=[C:12]([CH:14]=[O:15])[N:11]([CH3:16])[N:10]=2)=[CH:5][CH:4]=1.[CH3:17][C:18]1[C:22](B(O)O)=[C:21]([CH3:26])[O:20][N:19]=1.C([O-])([O-])=O.[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC.O>[CH3:17][C:18]1[C:22]([C:13]2[C:9]([C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)=[N:10][N:11]([CH3:16])[C:12]=2[CH:14]=[O:15])=[C:21]([CH3:26])[O:20][N:19]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27343463,5-Dimethylisoxazole-4-boronic acidHCID 83821626HCID 83821626, compound

Product 1

HCID 86668982HCID 86668982, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Procedure

A mixture of 4-bromo-3-(4-methoxyphenyl-1-methyl-1H-pyrazole-5-carbaldehyde (74.5 mg, 0.25 mmol), 3,5-dimethylisoxazol-4-ylboronic acid (53.4 mg, 0.38 mmol), K2CO3 (140 mg, 1.01 mmol) and Pd(PPh3)4 (14.6 mg, 0.01 mmol) in 1 DME/water (1 mL/1 mL) was flushed with argon and irradiated in the microwave at 140° C. for 30 min, extracted with EtOAc (3×4 mL) after 3 mL water were added. The mixture was concentrated and purified on silica gel to give 4-(3,5-dimethylisoxazol-4-yl)-3-(4-methoxyphenyl)-1-methyl-1H-pyrazole-5-carbaldehyde (25.6 mg, 0.08 mmol, 33%).

Workup

  1. customwas flushed with argon
  2. customirradiated in the microwave at 140° C. for 30 min
  3. extractionextracted with EtOAc (3×4 mL) after 3 mL water
  4. additionwere added
  5. concentrationThe mixture was concentrated
  6. custompurified on silica gel

Sources & evidence

ORD record
ord-93f6d5635bf9473685986a213cad45bb
Source dataset
uspto-grants-2014_12
Patent number
US08921402B2

Reaction notes

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