1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → HCID 58289702, compound

HRID 2088414Notes

Reaction equation

HRID 2088414 reaction equation
Br[C:2]1[N:7]=[C:6]2[N:8]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]4[N:23]=[CH:22][C:21]([Br:24])=[CH:20][N:19]=4)[CH:13]=3)[N:9]=[N:10][C:5]2=[N:4][CH:3]=1.[CH3:25][N:26]1[CH:30]=[C:29](B2OC(C)(C)C(C)(C)O2)[CH:28]=[N:27]1.O.O.O.P([O-])([O-])([O-])=[O:44].[K+].[K+].[K+]>COCCOC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:24][C:21]1[CH:20]=[N:19][C:18]([C:14]2[CH:13]=[C:12]([CH:17]=[CH:16][CH:15]=2)[CH2:11][N:8]2[C:6]3=[N:7][C:2]([O:44][C:29]4[CH:28]=[N:27][N:26]([CH3:25])[CH:30]=4)=[CH:3][N:4]=[C:5]3[N:10]=[N:9]2)=[N:23][CH:22]=1

Participants

6

Reactant 3

HCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 18407952Tripotassium phosphate trihydrateHCID 58289710HCID 58289710, compound

Product 1

HCID 58289702HCID 58289702, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

500 mg (0.932 mmol) of 6-bromo-1-[3-(5-bromopyrimidin-2-yl)benzyl]-1H-1,2,3-triazolo[4,5-b]pyrazine, 213 mg (1.03 mmol) of 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 396 mg (1.86 mmol) of tripotassium phosphate trihydrate are suspended in 20 ml of ethylene glycol dimethyl ether, degassed, evacuated and flushed with nitrogen a number of times. 65.4 mg (0.093 mmol) of bis(triphenylphosphine)palladium(II) chloride (15.2% of Pd) are added, and the mixture is again evacuated and flushed with nitrogen. The reaction mixture is stirred at 80° C. for 24 h. The reaction mixture is filtered, water is added to the filtrate, and the mixture is extracted with ethyl acetate. The organic phase is dried over sodium sulfate, evaporated under reduced pressure in a rotary evaporator and purified column-chromatically on silica gel.

Workup

  1. customdegassed
  2. customevacuated
  3. customflushed with nitrogen a number of times
  4. customthe mixture is again evacuated
  5. customflushed with nitrogen
  6. filtrationThe reaction mixture is filtered
  7. additionwater is added to the filtrate
  8. extractionthe mixture is extracted with ethyl acetate
  9. dry with materialThe organic phase is dried over sodium sulfate
  10. customevaporated under reduced pressure in a rotary evaporator
  11. custompurified column-chromatically on silica gel

Sources & evidence

ORD record
ord-867a4c9ecf4a4c098270220ea2fdbb95
Source dataset
uspto-grants-2013_05
Patent number
US08435986B2

Reaction notes

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