Potassium Carbonate → HCID 117798688, compound

HRID 1497361Notes

Reaction equation

HRID 1497361 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:8]2[C:4](=[C:5]([CH3:14])[N:6]([CH2:11][CH2:12][CH3:13])[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+].CN[C@@H]1CCCC[C@H]1NC>O1CCOCC1.[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]([CH2:11][CH2:12][CH3:13])[N:7]=4)[CH:3]=3)[C:24](=[O:28])[CH:23]=2)=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 574978644-[(4-Chlorophenyl)methoxy]pyridin-2(1H)-oneHCID 117798685HCID 117798685, compound

Product 1

HCID 117798688HCID 117798688, compoundYield 42.3%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 5-bromo-3-methyl-2-propyl-2H-indazole (110 mg), 4-[(4-chlorobenzyl)oxy]pyridin-2(1H)-one (82 mg) and potassium carbonate (179 mg) in 1,4-dioxane (5 ml) were added copper(I) iodide (32 mg) and trans-N,N′-dimethylcyclohexane-1,2-diamine (24 mg), and the mixture was stirred at 110° C. for 16 hr. The reaction mixture was cooled to room temperature, and concentrated under reduced pressure. To the residue were added dichloromethane and water, and the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (dichloromethane/methanol) to give the title compound (60 mg).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionTo the residue were added dichloromethane and water
  4. washthe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (dichloromethane/methanol)

Sources & evidence

ORD record
ord-cd4dc2b08ee34f56b7a793b805c7b6be
Source dataset
uspto-grants-2015_12
Patent number
US09199963B2

Reaction notes

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