Lithium Hexamethyldisilazide → N-(1-{[2-fluoro-6-(trifluoromethyl)phenyl]methyl}-1H-pyrazol-3-yl)-2-methylbenzamide

HRID 1946423

반응식

HRID 1946423 반응식
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:11][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].[F:26][C:27]1[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[C:28]=1[CH2:29]Br>C1COCC1.CS(C)=O>[F:26][C:27]1[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:36])([F:37])[F:38])[C:28]=1[CH2:29][N:19]1[CH:20]=[CH:21][C:17]([NH:16][C:14](=[O:15])[C:13]2[CH:22]=[CH:23][CH:24]=[CH:25][C:12]=2[CH3:11])=[N:18]1

참가 물질

6

반응물 3

HCID 2733832Lithium HexamethyldisilazideHCID 27375732-(Bromomethyl)-1-fluoro-3-(trifluoromethyl)benzeneHCID 178424292HCID 178424292, 화합물

생성물 1

HCID 59547859N-(1-{[2-fluoro-6-(trifluoromethyl)phenyl]methyl}-1H-pyrazol-3-yl)-2-methylbenzamide

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8028Tetrahydrofuran용매2회

실험 절차

1.0 M lithium bis(trimethylsilyl)amide (100 μl, 0.1 mmol, Aldrich) was slowly added to a solution of 2-methyl-N-1H-pyrazol-3-ylbenzamide (for a preparation see Intermediate 46)(22 mg, 0.1 mmol) in THF (400 μl). The resulting solution was then transferred to a solution of 2-fluoro-6-(trifluoromethyl)benzyl bromide (26 mg, 0.1 mmol, Aldrich) in THF (200 μl) and stirred for 1 h under nitrogen at ambient temperature. The mixture was diluted with DMSO (0.6 ml) and purified by MDAP using a Sunfire C18 (Method D) column 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 3) MH+=378, tRET=1.13 min.

후처리

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

출처 및 근거

ORD 기록
ord-e1bd2aa9fd4f4ffb913c7bfc0a1a7f4c
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399436B2

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