Hydrochloric Acid → 4-[4-bromo-5-chloro-2-(4,4-dimethyl-3,4-dihydro-2H-quinoline-1-sulfonyl)-phenoxy]-butan-1-ol

HRID 1891371노트

반응식

HRID 1891371 반응식
[CH2:1]([OH:6])[CH2:2][CH2:3][CH2:4][OH:5].[H-].[Na+].[Br:9][C:10]1[C:11]([Cl:32])=[CH:12][C:13](F)=[C:14]([S:16]([N:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]([CH3:30])([CH3:29])[CH2:21][CH2:20]2)(=[O:18])=[O:17])[CH:15]=1.Cl>CN(C=O)C>[Br:9][C:10]1[C:11]([Cl:32])=[CH:12][C:13]([O:5][CH2:4][CH2:3][CH2:2][CH2:1][OH:6])=[C:14]([S:16]([N:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]([CH3:30])([CH3:29])[CH2:21][CH2:20]2)(=[O:18])=[O:17])[CH:15]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 80641,4-ButanediolHCID 24758Sodium hydrideHCID 684692731-(5-Bromo-4-chloro-2-fluoro-benzenesulfonyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline

생성물 1

HCID 684721504-[4-bromo-5-chloro-2-(4,4-dimethyl-3,4-dihydro-2H-quinoline-1-sulfonyl)-phenoxy]-butan-1-ol수율 171%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

To a solution of 1,4-butanediol (0.44 mL, 5 mmole) in DMF (5 mL) at 0° C. was added sodium hydride (60%, 48 mg, 1.2 mmole) and the mixture stirred for 10 minutes. A solution of 1-(5-bromo-4-chloro-2-fluoro-benzenesulfonyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline (0.41 g, 1 mmole) in DMF (5 mL) was added. The mixture warmed to rt and was stirred for 1 hour. 1N hydrochloric acid solution (1 mL) was added and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and was dried over anhydrous MgSO4. Concentration of the filtrate provided a residue that was purified by silica gel chromatography [eluent: 40% ethyl acetate in hexane] to afford 4-[4-bromo-5-chloro-2-(4,4-dimethyl-3,4-dihydro-2H-quinoline-1-sulfonyl)-phenoxy]-butan-1-ol as a light yellow foam (0.86 g). MS: 503.9 (M+H)+; tR=2.66 min (method 1).

후처리

  1. stirringwas stirred for 1 hour
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialwas dried over anhydrous MgSO4
  5. customConcentration of the filtrate provided a residue that
  6. customwas purified by silica gel chromatography [eluent: 40% ethyl acetate in hexane]

출처 및 근거

ORD 기록
ord-062f058cb31b440bbea55cc328459345
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507536B2

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