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

HRID 1946422노트

반응식

HRID 1946422 반응식
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[Cl: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>[Cl: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]([CH2:29][C:28]2[C:31]([C:35]([F:36])([F:38])[F:37])=[CH:32][CH:33]=[CH:34][C:27]=2[F:26])[N:18]=1)=[O:15]

참가 물질

6

반응물 3

HCID 2733832Lithium HexamethyldisilazideHCID 27375732-(Bromomethyl)-1-fluoro-3-(trifluoromethyl)benzeneHCID 178522342HCID 178522342, 화합물

생성물 1

HCID 595479742-Chloro-N-(1-{[2-fluoro-6-(trifluoromethyl)phenyl]methyl}-1H-pyrazol-3-yl)benzamide

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-chloro-N-1H-pyrazol-3-ylbenzamide (for a preparation see Intermediate 45)(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 2 h under nitrogen at ambient temperature. The mixture was diluted with DMSO (0.6 ml) and purified by MDAP using a 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+=398, tRET=2.96 min.

후처리

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

출처 및 근거

ORD 기록
ord-3399d369b491410991ec97590013713a
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399436B2

반응 노트

불러오는 중…