Potassium Carbonate → {2-(4-Bromo-phenyl)-2-[4-(pyrazin-2-yloxy)-phenyl]-ethyl}-methyl-amine

HRID 2361796Notes

Reaction equation

HRID 2361796 reaction equation
C(OC(=O)[N:7]([CH2:9][CH:10]([C:18]1[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][CH:19]=1)[C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)[CH3:8])(C)(C)C.Cl[C:27]1[CH:32]=[N:31][CH:30]=[CH:29][N:28]=1.C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[Br:24][C:21]1[CH:20]=[CH:19][C:18]([CH:10]([C:11]2[CH:12]=[CH:13][C:14]([O:17][C:27]3[CH:32]=[N:31][CH:30]=[CH:29][N:28]=3)=[CH:15][CH:16]=2)[CH2:9][NH:7][CH3:8])=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 73277ChloropyrazineHCID 59331933[2-(4-Bromo-phenyl)-2-(4-hydroxy-phenyl)-ethyl]-methyl-carbamic acid tert-butyl ester

Product 1

HCID 59331924{2-(4-Bromo-phenyl)-2-[4-(pyrazin-2-yloxy)-phenyl]-ethyl}-methyl-amineYield 68.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of [2-(4-Bromo-phenyl)-2-(4-hydroxy-phenyl)-ethyl]-methyl-carbamic acid tert-butyl ester (125 mg, 0.31 mmol), 2-chloropyrazine (35.2 mg, 0.31 mmol) and K2CO3 (213 mg, 1.54 mmol) in dimethylformamide (8 ml) was heated to 100° C. for 17 hours. Upon cooling, the solvent was removed under reduced pressure and the residue was partitioned between ethyl acetate and saturated NaHCO3 solution. The organic layer was dried (MgSO4), filtered and concentrated. The crude product was then treated with saturated HCl in diethyl ether (15 ml) and stirred at room temperature for 72 hours. The solvent was then removed under reduced pressure and the crude product was purified by Phenomenex_Strata_SCX column chromatography eluting with methanol followed by 2N ammonia in methanol to afford the desired product (82 mg). LC/MS: (PS-B3) Rt 3.17 [M+H]+ 384.

Workup

  1. temperatureUpon cooling
  2. customthe solvent was removed under reduced pressure
  3. customthe residue was partitioned between ethyl acetate and saturated NaHCO3 solution
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. additionThe crude product was then treated with saturated HCl in diethyl ether (15 ml)
  8. customThe solvent was then removed under reduced pressure
  9. customthe crude product was purified by Phenomenex_Strata_SCX column chromatography
  10. washeluting with methanol

Sources & evidence

ORD record
ord-e71a0f9fae304083ac096b9928f72d6d
Source dataset
uspto-grants-2014_04
Patent number
US08691806B2

Reaction notes

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