Potassium Carbonate → HCID 59369326, compound

HRID 1689825Notes

Reaction equation

HRID 1689825 reaction equation
[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:10]=3[Cl:16])[C:5]=2[CH2:17][O:18][CH:19]2[CH2:25][CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[CH2:3][CH2:2]1.I[C:27]1[CH:37]=[CH:36][C:30]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:29][CH:28]=1.N1CCC[C@H]1C(O)=O.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.[Cu]I>[CH2:34]([O:33][C:31](=[O:32])[C:30]1[CH:36]=[CH:37][C:27]([N:22]2[CH2:23][CH2:24][CH2:25][CH:19]([O:18][CH2:17][C:5]3[C:6]([C:9]4[C:10]([Cl:16])=[CH:11][CH:12]=[CH:13][C:14]=4[Cl:15])=[N:7][O:8][C:4]=3[CH:1]3[CH2:2][CH2:3]3)[CH2:20][CH2:21]2)=[CH:28][CH:29]=1)[CH3:35]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 142891Ethyl 4-iodobenzoateHCID 145742L-ProlineHCID 593693374-((Azepan-4-yloxy)methyl)-5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazole

Product 1

HCID 59369326HCID 59369326, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 16 g (42 mmol) of 4-[5-cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazol-4-ylmethoxy]-azepane in 40 mL of dimethyl sulfoxide, is added ethyl 4-iodobenzoate (21 g, 67 mmol), proline (2 g, 16.7 mmol) and copper(I) iodide (3.2 g, 16.7 mmol.). The resulting mixture is degassed with nitrogen followed by addition of potassium carbonate (11.6 g, 84 mmol). The reaction mixture is stirred at 100° C. for 14 hours. The mixture is cooled to room temperature and quenched with water. The mixture is extracted with EtOAc, the organics are dried over MgSO4, filtered and concentrated to afford a crude which is purified on silica gel column chromatography (Eluting with Hexanes/EtOAc 8:2), to obtained 17 g of the title racemic compound.

Workup

  1. customThe resulting mixture is degassed with nitrogen
  2. temperatureThe mixture is cooled to room temperature
  3. customquenched with water
  4. extractionThe mixture is extracted with EtOAc
  5. dry with materialthe organics are dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford a crude which
  9. customis purified on silica gel column chromatography (Eluting with Hexanes/EtOAc 8:2)
  10. customto obtained 17 g of the title racemic compound

Sources & evidence

ORD record
ord-e20eaa7a9fe145a2983b04b86059b5bd
Source dataset
uspto-grants-2012_04
Patent number
US08153624B2

Reaction notes

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