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 1898121노트

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HRID 1898121 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-fc7251f665c3443c85419436d99892d1
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08519135B2

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