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Cesium carbonate → HCID 84689554, compound

HRID 340433
Notes
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Reaction equation

HRID 340433 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN1CCCC1=O.[NH:22]1[CH:26]=[CH:25][N:24]=[N:23]1>C(OCC)(=O)C.O>[Br:8][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([N:23]2[N:24]=[CH:25][CH:26]=[N:22]2)[CH:7]=1.[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([N:22]2[CH:26]=[CH:25][N:24]=[N:23]2)[CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 13387N-methyl-2-pyrrolidoneHCID 693693,5-DibromopyridineHCID 178418936HCID 178418936, compound

Product 2

HCID 84689554HCID 84689554, compoundHCID 84689556HCID 84689556, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

3,5-dibromopyridine (400 mg) and cesium carbonate (550 mg) were added to an N-methylpyrrolidone (4 ml) solution containing 1H-1,2,3-triazole (117 mg), followed by stirring at 100° C. for 21 hours. The reaction mixture was cooled to room temperature, and water and ethyl acetate were added. The organic layer was collected, washed with water and then with saturated saline, and dried over anhydrous magnesium sulfate, and the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel chromatography (hexane:ethyl acetate=10:0 to 2:3), and a white solid of 3-bromo-5-(2H-1,2,3-triazol-2-yl)pyridine (55 mg) and a white solid of 3-bromo-5-(1H-1,2,3-triazol-1-yl)pyridine (48 mg) were thus obtained.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe organic layer was collected
  3. washwashed with water
  4. dry with materialwith saturated saline, and dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled away under reduced pressure
  6. customThe obtained residue was purified by silica gel chromatography (hexane:ethyl acetate=10:0 to 2:3)

Sources & evidence

ORD record
ord-1639f6dd602547a5a401d7dbee601ace
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08895585B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes