Potassium Carbonate → HCID 58542074, compound

HRID 1966784Notes

Reaction equation

HRID 1966784 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH3:11][N:12]1[C:16]([CH3:17])=[C:15](B2OC(C)(C)C(C)(C)O2)[CH:14]=[N:13]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O.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>[CH3:11][N:12]1[C:16]([CH3:17])=[C:15]([C:2]2[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:9]=2)[CH:7]=[O:8])[CH:14]=[N:13]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 7363275-Bromo-2-fluorobenzaldehydeHCID 426473131,5-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Product 1

HCID 58542074HCID 58542074, compoundYield 74.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5-bromo-2-fluorobenzaldehyde (200 mg, 0.99 mmol) in DMF (5 mL) and H2O (1 mL) are added 1,5-dimethyl-1H-pyrazole-4-boronic acid pinacol ester (328 mg, 1.5 mmol), Pd(PPh3)4 (113 mg, 0.099 mmol) and K2CO3 (204 mg, 1.5 mmol) at room temperature. The solution is heated to 100° C. for 1 hour in a microwave reactor. The solution is cooled down and 3-mercaptopropyl-functionalized silica gel (500 mg) is added. The solution is stirred for 15 minutes and is filtered. The filtrate is washed with H2O (10 mL) and is extracted with EtOAc (3×10 mL). The combined organic layer is dried with MgSO4 (500 mg) and is filtered. The filtrate is concentrated and the residue is purified by silica gel flash chromatography with 20% EtOAc in Hepthane as the eluent to afford 5-(1,5-dimethyl-1H-pyrazol-4-yl)-2-fluoro-benzaldehyde (160 mg, 74%).

Workup

  1. temperatureThe solution is cooled down
  2. addition3-mercaptopropyl-functionalized silica gel (500 mg) is added
  3. filtrationis filtered
  4. washThe filtrate is washed with H2O (10 mL)
  5. extractionis extracted with EtOAc (3×10 mL)
  6. dry with materialThe combined organic layer is dried with MgSO4 (500 mg)
  7. filtrationis filtered
  8. concentrationThe filtrate is concentrated
  9. customthe residue is purified by silica gel flash chromatography with 20% EtOAc in Hepthane as the eluent

Sources & evidence

ORD record
ord-e71bf748813b467db2e07938ee830c79
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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