Pyridine → 5-bromo-4-chloro-2-fluoro-N-methyl-N-pyridin-2-yl-benzenesulfonamide

HRID 2382712노트

반응식

HRID 2382712 반응식
[Br:1][C:2]1[C:3]([Cl:13])=[CH:4][C:5]([F:12])=[C:6]([S:8](Cl)(=[O:10])=[O:9])[CH:7]=1.N1C=CC=CC=1.[CH3:20][NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1.[OH-].[Na+]>C(Cl)Cl>[Br:1][C:2]1[C:3]([Cl:13])=[CH:4][C:5]([F:12])=[C:6]([S:8]([N:21]([CH3:20])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)(=[O:10])=[O:9])[CH:7]=1

참가 물질

6

반응물 4

HCID 1049PyridineHCID 14798Sodium HydroxideHCID 207272-Pyridinamine, N-methyl-HCID 566047345-Bromo-4-chloro-2-fluoro-benzenesulfonyl chloride

생성물 1

HCID 684721885-bromo-4-chloro-2-fluoro-N-methyl-N-pyridin-2-yl-benzenesulfonamide수율 31%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To 5-bromo-4-chloro-2-fluorobenzenesulfonyl chloride (1.5 g, 4.89 mmol) in dry DCM (15 mL), at −20° C. was added pyridine (1.98 mL, 24.5 mmol) followed by methyl-pyridin-2-yl-amine (1.06 g, 9.78 mmol). The mixture was allowed to warm slowly to ambient temperature over 16 hrs. 1N NaOH solution (5 mL) was added and stirred for 15 mins. The mixture was extracted with DCM and the organics were washed with brine, dried over MgSO4 and the filtrate evaporated. The residue was purified by silica gel chromatography [eluent: 10% ethyl acetate in hexane] to give 5-bromo-4-chloro-2-fluoro-N-methyl-N-pyridin-2-yl-benzenesulfonamide as an oil (0.57 g, 31%). MS: 380.9 (M+H)+; tR=2.80 min (method 1).

후처리

  1. extractionThe mixture was extracted with DCM
  2. washthe organics were washed with brine
  3. dry with materialdried over MgSO4
  4. customthe filtrate evaporated
  5. customThe residue was purified by silica gel chromatography [eluent: 10% ethyl acetate in hexane]

출처 및 근거

ORD 기록
ord-4ad13fbee55b4c2ea65ada6207b94f58
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263588B2

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