Potassium Carbonate → HCID 59334644, compound

HRID 1639865Notes

Reaction equation

HRID 1639865 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:8]2[C:4](=[CH:5][N:6]([CH3:11])[N:7]=2)[C:3]=1[CH:12]1[CH2:14][CH:13]1[CH2:15][NH:16][C:17](=[O:19])[CH3:18].[CH3:20]B(O)O.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CN(C)C=O>[CH3:11][N:6]1[CH:5]=[C:4]2[C:8]([CH:9]=[CH:10][C:2]([CH3:20])=[C:3]2[CH:12]2[CH2:14][CH:13]2[CH2:15][NH:16][C:17](=[O:19])[CH3:18])=[N:7]1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 139377Methylboronic AcidHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 59334491HCID 59334491, compound

Product 1

HCID 59334644HCID 59334644, compoundYield 33.4%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

N-{[2-(5-Bromo-2-methyl-2H-indazol-4-yl)cyclopropyl]methyl}acetamide (200 mg, 0.621 mmol) obtained in Example 29, methylboronic acid (74.5 mg, 1.241 mmol), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (17.8 mg, 0.0372 mmol), potassium carbonate (206 mg, 1.49 mmol) and tris(dibenzylideneacetone)dipalladium(0) (22.7 mg, 0.0248 mmol) were added to N,N-dimethylformamide (3.1 mL), and the mixture was stirred under nitrogen atmosphere at 100° C. for 2 days, then stirred under heating at 120° C. for 2 days. The reaction solution was diluted with ethyl acetate, and filtered through celite. The obtained filtrate was washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate=0/100→5/95) and HPLC to give the title compound (53.4 mg, yield 33%).

Workup

  1. stirringstirred
  2. temperatureunder heating at 120° C. for 2 days
  3. filtrationfiltered through celite
  4. washThe obtained filtrate was washed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate=0/100→5/95) and HPLC

Sources & evidence

ORD record
ord-19f718a0e5de49b290beec26cd0a6096
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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