Lithium Hexamethyldisilazide → HCID 59547934, compound

HRID 1946420Notes

Reaction equation

HRID 1946420 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[F:11][C:12]1[CH:25]=[CH:24][CH:23]=[CH:22][C:13]=1[C:14]([NH:16][C:17]1[CH:21]=[CH:20][NH:19][N:18]=1)=[O:15].Br[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][C:29]=1[C:36]([F:39])([F:38])[F:37]>C1COCC1.CS(C)=O>[F:11][C:12]1[CH:25]=[CH:24][CH:23]=[CH:22][C:13]=1[C:14]([NH:16][C:17]1[CH:21]=[CH:20][N:19]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][C:29]=2[C:36]([F:37])([F:38])[F:39])[N:18]=1)=[O:15]

Participants

6

Reactant 3

HCID 2733832Lithium HexamethyldisilazideHCID 467375744-Methoxy-2-(trifluoromethyl)benzyl bromideHCID 178522343HCID 178522343, compound

Product 1

HCID 59547934HCID 59547934, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

1.0 M lithium bis(trimethylsilyl)amide (100 μl, 0.1 mmol, Aldrich) was slowly added to a solution of 2-fluoro-N-1H-pyrazol-3-ylbenzamide (for a preparation see Intermediate 43) (20.5 mg, 0.1 mmol) in THF (400 μl). The resulting solution was then transferred to a solution of 1-(bromomethyl)-4-(methyloxy)-2-(trifluoromethyl)benzene 24.7 mg, 0.1 mmol, JRD Fluorochemicals Ltd) in THF (200 μl) and stirred for 2 h under nitrogen at ambient temperature. The mixture was diluted with DMSO (0.6 ml) and purified by MDAP using the Sunfire C18 column (Method D) using Acetonitrile-Water with a TFA modifier. The solvent was removed under a stream of nitrogen to give the title compound (27 mg). LCMS (System 4)

Workup

  1. custompurified by MDAP
  2. customThe solvent was removed under a stream of nitrogen

Sources & evidence

ORD record
ord-337a1fa4090f47ee82b68793ad1e6a08
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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