Ammonia → 4-(benzyloxy)-1-(2,3-dimethyl-2H-indazol-5-yl)pyridin-2(1H)-one

HRID 1497370Notes

Reaction equation

HRID 1497370 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:8]2[C:4](=[C:5]([CH3:12])[N:6]([CH3:11])[N:7]=2)[CH:3]=1.[CH2:13]([O:20][C:21]1[CH:26]=[CH:25][NH:24][C:23](=[O:27])[CH:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].CNCCNC.N>CS(C)=O.[Cu]I>[CH2:13]([O:20][C:21]1[CH:26]=[CH:25][N:24]([C:2]2[CH:10]=[CH:9][C:8]3[C:4](=[C:5]([CH3:12])[N:6]([CH3:11])[N:7]=3)[CH:3]=2)[C:23](=[O:27])[CH:22]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

8

Reactant 5

HCID 222AmmoniaHCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 36077244-Benzyloxy-2(1H)-pyridoneHCID 114995675-bromo-2,3-dimethyl-2H-indazole

Product 1

HCID 1178168034-(benzyloxy)-1-(2,3-dimethyl-2H-indazol-5-yl)pyridin-2(1H)-oneYield 65.3%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
150 °C

Procedure

A suspension of 5-bromo-2,3-dimethyl-2H-indazole (1.85 g), 4-(benzyloxy)pyridin-2(1H)-one (1.65 g), potassium carbonate (3.41 g), copper(I) iodide (1.57 g) and N,N′-dimethylethylenediamine (0.73 g) in DMSO (30 ml) was stirred at 150° C. for 3 hr. The reaction mixture was cooled to room temperature, and added to 28% aqueous ammonia, and the obtained precipitates were collected by filtration. The obtained solid was washed with water and diisopropyl ether, and dried under reduced pressure to give the title compound (1.85 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe obtained precipitates
  3. filtrationwere collected by filtration
  4. washThe obtained solid was washed with water and diisopropyl ether
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-74c313ec6f764a3b8058f3700090c7b2
Source dataset
uspto-grants-2015_12
Patent number
US09199963B2

Reaction notes

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