N-(2-Bromo-5-chloro-pyridin-3-yl)-4-chloro-N-methoxvmethyl-3-trifluoromethyl-benzenesulfonamide → 4-Chloro-N-[5-chloro-2-(2-oxazol-2-yl-benzoyl)-Pyridin-3-yl]-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide

HRID 419114노트

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HRID 419114 반응식
Br[C:2]1[C:7]([N:8]([CH2:23][O:24][CH3:25])[S:9]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([C:19]([F:22])([F:21])[F:20])[CH:13]=2)(=[O:11])=[O:10])=[CH:6][C:5]([Cl:26])=[CH:4][N:3]=1.C([Mg]Cl)(C)C.CON(C)[C:35](=[O:47])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[C:42]1[O:43][CH:44]=[CH:45][N:46]=1>C1COCC1>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([S:9]([N:8]([C:7]2[C:2]([C:35](=[O:47])[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[C:42]3[O:43][CH:44]=[CH:45][N:46]=3)=[N:3][CH:4]=[C:5]([Cl:26])[CH:6]=2)[CH2:23][O:24][CH3:25])(=[O:11])=[O:10])=[CH:13][C:14]=1[C:19]([F:22])([F:21])[F:20]

참가 물질

5

반응물 3

HCID 57942086N-(2-Bromo-5-chloro-pyridin-3-yl)-4-chloro-N-methoxvmethyl-3-trifluoromethyl-benzenesulfonamideHCID 57942199N-Methoxy-N-methyl-2-oxazol-2-yl-benzamideHCID 178418918HCID 178418918, 화합물

생성물 1

HCID 579423584-Chloro-N-[5-chloro-2-(2-oxazol-2-yl-benzoyl)-Pyridin-3-yl]-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide수율 20.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a solution of N-(2-Bromo-5-chloro-pyridin-3-yl)-4-chloro-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide (125 mg, 0.25 mmol) in 2.0 mL of THF under nitrogen atmosphere at 0° C. was added drop-wise 0.3 ml (0.6 mmol) of isopropylmagnesium chloride. The mixture was then stirred for 20 min at 0° C. followed by addition of N-Methoxy-N-methyl-2-oxazol-2-yl-benzamide (100 mg, 0.43 mmol). The mixture was stirred at room temperature overnight, quenched with saturated ammonium chloride and extracted with ethyl acetate. After concentration the residue was purified by flash chromatograph (30% ethyl acetate in hexane) to afford 30 mg of title compound as an off white solid. MS: (M+H)/z=586.1.

후처리

  1. stirringThe mixture was stirred at room temperature overnight
  2. customquenched with saturated ammonium chloride
  3. extractionextracted with ethyl acetate
  4. concentrationAfter concentration the residue
  5. customwas purified by flash chromatograph (30% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-444cedb558c2488086962e7cc137793f
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093247B2

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