3,5-Bis(trifluoromethyl)benzyl bromide → HCID 9872837, compound

HRID 1975957Notes

Reaction equation

HRID 1975957 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:13]([C:14]([NH:16][CH3:17])=[O:15])=[CH:12][C:11]([N:18]2[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]2)=[N:10][CH:9]=1.C[Si](C)(C)[N-][Si](C)(C)C.[K+].[F:35][C:36]([F:50])([F:49])[C:37]1[CH:38]=[C:39]([CH:42]=[C:43]([C:45]([F:48])([F:47])[F:46])[CH:44]=1)[CH2:40]Br>O1CCCC1>[F:35][C:36]([F:50])([F:49])[C:37]1[CH:38]=[C:39]([CH:42]=[C:43]([C:45]([F:48])([F:47])[F:46])[CH:44]=1)[CH2:40][N:16]([CH3:17])[C:14](=[O:15])[C:13]1[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])=[CH:9][N:10]=[C:11]([N:18]2[CH2:19][CH2:20][N:21]([CH3:24])[CH2:22][CH2:23]2)[CH:12]=1

Participants

5

Reactant 3

HCID 1225733,5-Bis(trifluoromethyl)benzyl bromideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 11450797HCID 11450797, compound

Product 1

HCID 9872837HCID 9872837, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 0.074 g (0.21 mmol) 5-(2-chloro-phenyl)-N-methyl-2-(4-methyl-piperazin-1-yl)-isonicotinamide in 5 ml tetrahydrofuran at −10° C. were added dropwise 0.29 ml (0.29 mmol) of 1 M potassium hexamethyldisilazide solution in tetrahydrofuran. Stirring was continued for ½ h at −10° C. At this temperature 0.42 ml 3.5-bis(trifluormethyl)-benzylbromide were added. The reaction was quenched with water after 10 min and the mixture was extracted with three 15 ml portions of ethyl acetate. The combined organic layers were washed with brine, dried (magnesium sulfate) and evaporated. Chromatography of the residue afforded 0.113 g (92%) of the title compound as a pale yellow oil.

Workup

  1. customThe reaction was quenched with water after 10 min
  2. extractionthe mixture was extracted with three 15 ml portions of ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (magnesium sulfate)
  5. customevaporated

Sources & evidence

ORD record
ord-ded54e33923346688cc242d1e47f2d00
Source dataset
uspto-grants-2001_05
Patent number
US06225316B1

Reaction notes

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