Potassium Carbonate → HCID 57405007, compound

HRID 1520079Notes

Reaction equation

HRID 1520079 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[C:11]1[N:12]=[N:13][N:14]([C:16]2[CH:32]=[CH:31][C:19]([C:20]([N:22]3[CH2:27][CH2:26][CH:25]([N:28]([CH3:30])[CH3:29])[CH2:24][CH2:23]3)=[O:21])=[CH:18][CH:17]=2)[CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O>[CH3:30][N:28]([CH3:29])[CH:25]1[CH2:26][CH2:27][N:22]([C:20](=[O:21])[C:19]2[CH:31]=[CH:32][C:16]([N:14]3[CH:15]=[C:11]([C:5]4[C:4]5[C:8](=[CH:9][CH:10]=[C:2]([CH:3]=[C:4]([CH3:8])[CH3:5])[CH:3]=5)[NH:7][N:6]=4)[N:12]=[N:13]3)=[CH:17][CH:18]=2)[CH2:23][CH2:24]1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 67981399HCID 67981399, compound2×

Product 1

HCID 57405007HCID 57405007, compoundYield 90.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1-{4-[4-(5-bromo-1H-indazol-3-yl)-1H-1,2,3-triazol-1-yl]benzoyl}-N,N-dimethylpiperidin-4-amine (160 mg; 0.32 mmol; 1.0 eq.), 1-{4-[4-(5-bromo-1H-indazol-3-yl)-1H-1,2,3-triazol-1-yl]benzoyl}-N,N-dimethylpiperidin-4-amine (160 mg; 0.32 mmol; 1.0 eq.), PdCl2dppf (24 mg; 0.03 mmol; 0.1 eq.) and potassium carbonate (224 mg; 1.62 mmol; 5.0 eq.) in dioxane (1 mL) and water (1 mL) was heated at 80° C. O/N in a sealed tube. The reaction mixture was then filtered through a celite pad and filtrate was extracted twice with DCM. Combined organic phases were washed with brine, dried over magnesium sulfate, filtered and concentrated. Purification by flash chromatography on silica (DCM:MeOH, gradient form 90:10 to 50:50) gave the title compound as a brown powder (68 mg, 45%).

Workup

  1. filtrationThe reaction mixture was then filtered through a celite pad and filtrate
  2. extractionwas extracted twice with DCM
  3. washCombined organic phases were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash chromatography on silica (DCM:MeOH, gradient form 90:10 to 50:50)

Sources & evidence

ORD record
ord-7256a9b6ef364585b3ec9dff2ef76cd8
Source dataset
uspto-grants-2015_07
Patent number
US09073892B2

Reaction notes

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