Potassium Carbonate → HCID 68163163, compound

HRID 2400337Notes

Reaction equation

HRID 2400337 reaction equation
Cl.[NH:2]1[CH2:5][CH:4]([N:6]2[CH:10]=[C:9]([Br:11])[CH:8]=[N:7]2)[CH2:3]1.C([O-])([O-])=O.[K+].[K+].Br[CH2:19][CH2:20][O:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][O:23]1>CC#N>[Br:11][C:9]1[CH:8]=[N:7][N:6]([CH:4]2[CH2:5][N:2]([CH2:19][CH2:20][O:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][O:23]3)[CH2:3]2)[CH:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 670275871201657-76-2

Product 1

HCID 68163163HCID 68163163, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 1-Azetidin-3-yl-4-bromo-1H-pyrazole hydrochloride (0.3 g, 1.26 mmol) in CH3CN (15 ml) added K2CO3(0.78 g, 5.6 mmol) followed by 2-(2-bromoethoxy)tetrahydro-2H-pyran (0.205 ml, 1.5 mmol) reaction heated at reflux 0/N. Reaction mixture filtered, solid washed with EtOAc, filtrate concentrated under reduced pressure, residue partitioned between CH2Cl2 and H2O. The organic layer was separated, dried over MgSO4, filtered and concentrated under reduced pressure to give the product (380 mg).

Workup

  1. temperatureheated
  2. temperatureat reflux 0/N
  3. customReaction mixture
  4. filtrationfiltered
  5. washsolid washed with EtOAc, filtrate
  6. concentrationconcentrated under reduced pressure, residue
  7. custompartitioned between CH2Cl2 and H2O
  8. customThe organic layer was separated
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-44edaaddcbb14c33ac0880c0e9a9039b
Source dataset
uspto-grants-2014_08
Patent number
US08796244B2

Reaction notes

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