4-Fluorobenzenesulfonyl chloride → N-(4-(4-methoxybenzyloxy)-3-bromobenzyl)-4-fluoro-N-methylbenzenesulfonamide

HRID 68616노트

반응식

HRID 68616 반응식
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][NH:16][CH3:17])=[CH:11][C:10]=2[Br:18])=[CH:5][CH:4]=1.[F:21][C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][N:16]([CH3:17])[S:28]([C:25]3[CH:26]=[CH:27][C:22]([F:21])=[CH:23][CH:24]=3)(=[O:30])=[O:29])=[CH:11][C:10]=2[Br:18])=[CH:5][CH:4]=1

참가 물질

5

반응물 3

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 63045147(4-(4-methoxybenzyloxy)-3-bromophenyl)-N-methylmethanamine

생성물 1

HCID 66869194N-(4-(4-methoxybenzyloxy)-3-bromobenzyl)-4-fluoro-N-methylbenzenesulfonamide수율 63%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of intermediate 33 (2.7 g, 8.0 mmol, 1 eq) in DCM (10 mL) was added 4-fluorobenzene-1-sulfonyl chloride (1.9 g, 9.6 mmol, 1.2 eq) and DIEA (2.8 mL, 16.0 mmol, 2 eq). After stirring at room temperature for 1 h, the reaction was washed with saturated NaHCO3 and brine, dried (Na2SO4), and concentrated in vacuo. The crude product was purified via silica gel chromatography (0-40% EtOAc/hexane) to give 2.48 g (63%) of N-(4-(4-methoxybenzyloxy)-3-bromobenzyl)-4-fluoro-N-methylbenzenesulfonamide (34).

후처리

  1. washthe reaction was washed with saturated NaHCO3 and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified via silica gel chromatography (0-40% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-b2e061bbd6374298b51da5dc80af701b
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822467B2

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