Morpholine → 4-(4-(2-Bromo-pyridin-4-yl)-3-phenyl-isoxazol-5-ylmethyl)-morpholine

HRID 1375642Notes

Reaction equation

HRID 1375642 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]2[C:9]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:10][O:11][C:12]=2[CH2:13]Br)[CH:5]=[CH:4][N:3]=1.[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.[Cl-].[Na+].O>[Br:1][C:2]1[CH:7]=[C:6]([C:8]2[C:9]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:10][O:11][C:12]=2[CH2:13][N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 234356442-Bromo-4-(5-bromomethyl-3-phenyl-isoxazol-4-yl)-pyridine

Product 1

HCID 234356454-(4-(2-Bromo-pyridin-4-yl)-3-phenyl-isoxazol-5-ylmethyl)-morpholineYield 94.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A stirred solution of the above Compound 18a (484 mg, 1.22 mmol), morpholine (0.45 mL, 5.1 mmol) and K2CO3 (340 mg, 2.45 mmol) in anhydrous DMF (2 mL) was warmed to 40° C. for 18 h. The solution was poured into brine (10 ml), extracted with CH2Cl2 (3×15 mL), dried (MgSO4), and filtered. Flash chromatography (SiO2, 50% EtOAc-hexanes) provided the title compound (461 mg, 1.15 mmol, 94%).

Workup

  1. extractionextracted with CH2Cl2 (3×15 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered

Sources & evidence

ORD record
ord-b8852cd95a2d45fb87ce4e12b1325938
Source dataset
uspto-grants-2007_01
Patent number
US07169798B2

Reaction notes

Loading…