Potassium Carbonate → HCID 13008382, compound

HRID 2083848Notes

Reaction equation

HRID 2083848 reaction equation
[CH2:1]([NH:8][C:9]1[N:13]([CH2:14][CH2:15][CH2:16][N:17]2[C:21]([NH:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[C:20]([N+:30]([O-:32])=[O:31])[C:19](Br)=[N:18]2)[N:12]=[C:11](Br)[C:10]=1[N+:35]([O-:37])=[O:36])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:38]1(OB(O)O)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.O>[CH2:1]([NH:8][C:9]1[N:13]([CH2:14][CH2:15][CH2:16][N:17]2[C:21]([NH:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[C:20]([N+:30]([O-:32])=[O:31])[C:19]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[N:18]2)[N:12]=[C:11]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:10]=1[N+:35]([O-:37])=[O:36])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 78412Phenyl dihydrogen orthoborateHCID 13008380HCID 13008380, compound

Product 1

HCID 13008382HCID 13008382, compoundYield 81.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

3.7 g of 1,3-bis-(5-benzylamino-3-bromo-4-nitropyrazol-1-yl)propane from step 5.2 in 40 ml 1,2-dimethoxyethane are mixed under nitrogen with 3.8 g phenyl boric acid, 1.2 g of tetrakis(triphenylphosphin)palladium (0) and a solution of 8.3 g of potassium carbonate in 30 ml water. The resulting reaction mixture is subsequently heated under reflux under nitrogen. After five hours the reaction mixture is heated over silica gel (hyflo super-gel of Celite Co.), filtered and the filtrate cooled in an ice bath. The precipitate coming down is filtered, washed with water and recrystallized from 50 ml ethanol. After drying in vacuum at 60° C. one obtains 1.5 g of a yellow product.

Workup

  1. customThe resulting reaction mixture
  2. temperatureis subsequently heated
  3. temperatureunder reflux under nitrogen
  4. temperatureAfter five hours the reaction mixture is heated over silica gel (hyflo super-gel of Celite Co.)
  5. filtrationfiltered
  6. temperaturethe filtrate cooled in an ice bath
  7. filtrationThe precipitate coming down is filtered
  8. washwashed with water
  9. customrecrystallized from 50 ml ethanol
  10. customAfter drying in vacuum at 60° C. one

Sources & evidence

ORD record
ord-55eb64671ac74a3ba958f5994cc5c24c
Source dataset
uspto-grants-2004_04
Patent number
US06716257B2

Reaction notes

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