Ammonia → 4-[(4-chlorobenzyl)oxy]-1-(2-cyclopropyl-3-methyl-2H-indazol-5-yl)pyridin-2(1H)-one

HRID 1497365Notes

Reaction equation

HRID 1497365 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:8]2[C:4](=[C:5]([CH3:14])[N:6]([CH:11]3[CH2:13][CH2:12]3)[N:7]=2)[CH:3]=1.[Cl:15][C:16]1[CH:30]=[CH:29][C:19]([CH2:20][O:21][C:22]2[CH:27]=[CH:26][NH:25][C:24](=[O:28])[CH:23]=2)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].CNCCNC.N>CS(C)=O.[Cu]I>[Cl:15][C:16]1[CH:30]=[CH:29][C:19]([CH2:20][O:21][C:22]2[CH:27]=[CH:26][N:25]([C:2]3[CH:10]=[CH:9][C:8]4[C:4](=[C:5]([CH3:14])[N:6]([CH:11]5[CH2:13][CH2:12]5)[N:7]=4)[CH:3]=3)[C:24](=[O:28])[CH:23]=2)=[CH:18][CH:17]=1

Participants

8

Reactant 5

HCID 222AmmoniaHCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 574978644-[(4-Chlorophenyl)methoxy]pyridin-2(1H)-oneHCID 1177986405-bromo-2-cyclopropyl-3-methyl-2H-indazole

Product 1

HCID 1177987444-[(4-chlorobenzyl)oxy]-1-(2-cyclopropyl-3-methyl-2H-indazol-5-yl)pyridin-2(1H)-oneYield 38.9%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

To a suspension of 5-bromo-2-cyclopropyl-3-methyl-2H-indazole (320 mg), 4-[(4-chlorobenzyl)oxy]pyridin-2(1H)-one (200 mg) and potassium carbonate (352 mg) in DMSO (20 ml) were added copper(I) iodide (162 mg) and N,N′-dimethylethylenediamine (112 mg), and the mixture was reacted at 150° C. for 1 hr under microwave irradiation. The reaction mixture was added to 28% aqueous ammonia, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/methanol) and recrystallized from ethyl acetate to give the title compound (134 mg).

Workup

  1. customthe mixture was reacted at 150° C. for 1 hr under microwave irradiation
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/methanol)
  7. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-b0d40714caf64cb086c2869e82d9931f
Source dataset
uspto-grants-2015_12
Patent number
US09199963B2

Reaction notes

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