1-Bromo-4-(trifluoromethoxy)benzene → HCID 59706965, compound

HRID 217647Notes

Reaction equation

HRID 217647 reaction equation
[CH3:1][C@@H:2]1[CH2:7][NH:6][CH2:5][CH2:4][NH:3]1.[F:8][C:9]([F:19])([F:18])[O:10][C:11]1[CH:16]=[CH:15][C:14](Br)=[CH:13][CH:12]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][C@H:2]1[NH:3][CH2:4][CH2:5][N:6]([C:14]2[CH:13]=[CH:12][C:11]([O:10][C:9]([F:8])([F:18])[F:19])=[CH:16][CH:15]=2)[CH2:7]1

Participants

7

Reactant 3

HCID 5210081-Bromo-4-(trifluoromethoxy)benzeneHCID 73304342-Methylpiperazine, (R)-HCID 23676156Sodium t-butoxide

Product 1

HCID 59706965HCID 59706965, compoundYield 41.9%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 634876Binap, (A+-)-CatalystHCID 1140TolueneSolvent

Procedure

To a mixture of (R)-2-methylpiperazine (3.0 g, 30 mmol), 4-trifluoromethoxy bromo benzene (6.6 g, 27.5 mmol) and sodium tert-butoxide (3.56 g, 37.5 mmol) in dry toluene (50 mL) under nitrogen atmosphere, were added Pd(OAc)2 (0.28 g, 12.5 mmol) followed by BINAP (0.62 g, 1 mmol) and refluxed for 16 h. Then the reaction mixture was concentrated and the crude compound was purified by column chromatography on silica gel using chloroform and methanol as eluent to give the title compound as a dark brown liquid (3 g, 38%).

Workup

  1. temperaturerefluxed for 16 h
  2. concentrationThen the reaction mixture was concentrated
  3. customthe crude compound was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-d20db1cf6cb949a7b9575f5b85054e7b
Source dataset
uspto-grants-2012_06
Patent number
US08198280B2

Reaction notes

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