Lithium Hexamethyldisilazide → HCID 59547951, compound

HRID 1946421Notes

Reaction equation

HRID 1946421 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[Cl:11][C:12]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:13]=1[C:14]([NH:16][C:17]1[CH:21]=[CH:20][NH:19][N:18]=1)=[O:15].Br[CH2:28][C:29]1([CH:36]=[CH:35][CH:34]=[CH:33][CH:32]1[C:37]([F:40])([F:39])[F:38])CBr>C1COCC1.CS(C)=O>[Cl:11][C:12]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:13]=1[C:14]([NH:16][C:17]1[CH:21]=[CH:20][N:19]([CH2:28][C:29]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[C:37]([F:38])([F:39])[F:40])[N:18]=1)=[O:15]

Participants

6

Reactant 3

HCID 2733832Lithium HexamethyldisilazideHCID 66772165HCID 66772165, compoundHCID 178522345HCID 178522345, compound

Product 1

HCID 59547951HCID 59547951, 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 2,6-dichloro-N-1H-pyrazol-3-ylbenzamide (for a preparation see Intermediate 44)(26 mg, 0.1 mmol) in THF (400 μl). The resulting solution was then transferred to a solution of 1-(bromomethyl)-2-(trifluoromethyl)benzyl bromide (24.7 mg, 0.1 mmol, Apollo Scientific Limited) 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) MH+=415, tRET=3.11 min.

Workup

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

Sources & evidence

ORD record
ord-34bcb9af6d05494e85c5db38f07d0d6e
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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