Pyridine → 5-Bromo-pyridine-2-sulfonic acid (4-fluoro-phenyl)-isobutyl-amide

HRID 623363노트

반응식

HRID 623363 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:8](Cl)(=[O:10])=[O:9])=[N:6][CH:7]=1.N1C=CC=CC=1.[F:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][CH2:26][CH:27]([CH3:29])[CH3:28])=[CH:21][CH:20]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[F:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]([CH2:26][CH:27]([CH3:29])[CH3:28])[S:8]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)(=[O:10])=[O:9])=[CH:21][CH:20]=1

참가 물질

7

반응물 4

HCID 1049PyridineHCID 516892Sodium BicarbonateHCID 185437114-Fluoro-N-(2-methylpropyl)anilineHCID 445580975-Bromopyridine-2-sulfonyl chloride

생성물 1

HCID 867218735-Bromo-pyridine-2-sulfonic acid (4-fluoro-phenyl)-isobutyl-amide수율 82.9%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 5-bromo-pyridine-2-sulfonyl chloride (330 mg, 1.29 mmol) in DCM (10 mL) was added pyridine (208 μL, 2.57 mmol) followed by a solution of (4-fluoro-phenyl)-isobutyl-amine (215 mg, 1.29 mmol) in DCM (10 mL) and the reaction was stirred at room temperature for 16 hours. Water and saturated aqueous NaHCO3 were added and then extracted with DCM, filtered through a phase separator, concentrated then purified by silica gel column chromatography (0-20% EtOAc in cyclohexane) to give 5-bromo-pyridine-2-sulfonic acid (4-fluoro-phenyl)-isobutyl-amide (414 mg, 78%). LCMS (m/z, Method A) ES+ 387/389 [M+1]+.

후처리

  1. extractionextracted with DCM
  2. filtrationfiltered through a phase separator
  3. concentrationconcentrated
  4. customthen purified by silica gel column chromatography (0-20% EtOAc in cyclohexane)

출처 및 근거

ORD 기록
ord-7db6ec00e5934fa78fb19a674a039574
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09302985B2

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