Water → HCID 68734747, compound

HRID 2068694Notes

Reaction equation

HRID 2068694 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][N:3]=1.[OH-].[K+].Cl[CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.O>CS(C)=O>[Br:8][C:6]1[CH:5]=[CH:4][N:3]([CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:2](=[O:1])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 767274-(2-Chloroethyl)morpholineHCID 178515446HCID 178515446, compound

Product 1

HCID 68734747HCID 68734747, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2-hydroxy-4-bromopyridine (0.10 g, 0.57 mmol) in DMSO (1.0 mL) was added KOH (0.13 g, 2.29 mmol) and the resulting reaction mixture was stirred for 10 min at room temperature followed by addition of 4-(2-chloroethyl)morpholine (0.13 g, 0.69 mmol). The reaction mixture was then stirred at 45° C. for 30 min. After the completion of reaction (TLC monitoring), water was added to the reaction and extracted with EtOAc (3×25 mL). The combined organics was washed with brine, dried (Na2SO4), filtered and concentrated. The residue was purified over silica gel (100-200 M, 5% MeOH-DCM) to obtain the desired product (0.085 g, 52%). MS: 287.10 (M+H)+.

Workup

  1. customthe resulting reaction mixture
  2. stirringThe reaction mixture was then stirred at 45° C. for 30 min
  3. additionwas added to the reaction
  4. extractionextracted with EtOAc (3×25 mL)
  5. washThe combined organics was washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified over silica gel (100-200 M, 5% MeOH-DCM)

Sources & evidence

ORD record
ord-f26b74c0346a495289827da470eff92f
Source dataset
uspto-grants-2012_10
Patent number
US08299065B2

Reaction notes

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