Cesium carbonate → HCID 84689554, compound

HRID 2406688Notes

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

Participants

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

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

Sources & evidence

ORD record: ord-752d98e730004cb8bde1653063a78559
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809371B2

Reaction notes

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