Tris(1,1-dimethylethyl)phosphine → N-methyl-2-nitro-4-(4-trifluoromethyl-piperidin-1-yl)-aniline

HRID 1258674Notes

Reaction equation

HRID 1258674 reaction equation
C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.Br[C:15]1[CH:22]=[CH:21][C:18]([NH:19][CH3:20])=[C:17]([N+:23]([O-:25])=[O:24])[CH:16]=1.[F:26][C:27]([F:35])([F:34])[CH:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:20][NH:19][C:18]1[CH:21]=[CH:22][C:15]([N:31]2[CH2:32][CH2:33][CH:28]([C:27]([F:35])([F:34])[F:26])[CH2:29][CH2:30]2)=[CH:16][C:17]=1[N+:23]([O-:25])=[O:24]

Participants

6

Reactant 3

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 1364694-(Trifluoromethyl)piperidineHCID 2580424-Bromo-N-methyl-2-nitroaniline

Product 1

HCID 67958090N-methyl-2-nitro-4-(4-trifluoromethyl-piperidin-1-yl)-aniline

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
100 °C

Procedure

Under argon sodium tert-butoxide (366 mg, 3.8 mmol) followed by palladium(II) acetate (22 mg, 0.1 mmol) and tri-tert-butylphosphine 10% in toluene (450 μL, 0.2 mmol) were added to a mixture of 4-bromo-2-nitro-N-methyl-aniline (440 mg, 1.9 mmol) and 4-(trifluoromethyl)piperidine (660 mg, 2.9 mmol) in toluene (7 mL). The reaction mixture was stirred at 100° C. overnight then allowed to cool and was concentrated. The crude was purified by chromatography to give the sub-title compound.

Workup

  1. temperatureto cool
  2. concentrationwas concentrated
  3. customThe crude was purified by chromatography

Sources & evidence

ORD record
ord-c5577096a9b1464f8cc674db26297e53
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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