Water → HCID 58289778, compound

HRID 2088413Notes

Reaction equation

HRID 2088413 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.C(=O)([O-])[O-].[Na+].[Na+].O>>[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]([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

5

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 58289710HCID 58289710, compound

Product 1

HCID 58289778HCID 58289778, compound

Conditions

Temperature
80 °C

Procedure

2.00 g (3.67 mmol) of 6-bromo-1-[3-(5-bromopyrimidin-2-yl)benzyl]-1H-1,2,3-triazolo[4,5-b]pyrazine, 840 mg (4.04 mmol) of 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 778 mg (7.34 mmol) of sodium carbonate are suspended in 3.7 ml (204 mmol) of water and 15 ml of N,N-dimethylformamide, degassed, evacuated and flushed with nitrogen a number of times. 257 mg (0.367 mmol) of bis(triphenylphosphine)palladium-(II) chloride 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 and washed with ethyl acetate and evaporated. The residue is stirred with isopropanol and reacted further without additional purification.

Workup

  1. custom15 ml of N,N-dimethylformamide, degassed
  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. washwashed with ethyl acetate
  8. customevaporated
  9. stirringThe residue is stirred with isopropanol
  10. customreacted further without additional purification

Sources & evidence

ORD record
ord-23735f9b051b4010b894a6097a8309ed
Source dataset
uspto-grants-2013_05
Patent number
US08435986B2

Reaction notes

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