Potassium Carbonate → HCID 68004132, compound

HRID 2209168Notes

Reaction equation

HRID 2209168 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([F:9])[C:5](Cl)=[N:6][CH:7]=1.[N:10]1([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.C(OCC)C>[Br:1][C:2]1[CH:3]=[C:4]([F:9])[C:5]([N:13]2[CH2:12][CH2:11][N:10]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14]2)=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27632855-Bromo-2-chloro-3-fluoropyridine

Product 1

HCID 68004132HCID 68004132, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Procedure

In a pressure tube, 5-bromo-2-chloro-3-fluoropyridine (7.89 ml, 49.9 mmol), tert-butyl piperazine-1-carboxylate (9293.48 mg, 49.9 mmol), potassium carbonate (8275.33 mg, 59.88 mmol) in dimethylsulfoxide (40 ml) were combined and refluxed at 120 C for ovn. The reaction was cooled down, diluted with ethyl ether (100 mL). The solution was washed with water (40 mL×2), brine (50 mL), filtered, dried, and concentrated. The reaction was purified on silica by flash chromatography to provide of tert-butyl 4-(5-bromo-3-fluoropyridin-2-yl)piperazine-1-carboxylate (5000 mg, 28%).

Workup

  1. temperaturerefluxed at 120 C for ovn
  2. temperatureThe reaction was cooled down
  3. washThe solution was washed with water (40 mL×2), brine (50 mL)
  4. filtrationfiltered
  5. customdried
  6. concentrationconcentrated
  7. customThe reaction was purified on silica by flash chromatography

Sources & evidence

ORD record
ord-a7294fdb667a461aab49df2bd106dadc
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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