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

HRID 1891371ノート

反応式

HRID 1891371 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

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).

後処理

  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]

出典と根拠

ORDレコード
ord-062f058cb31b440bbea55cc328459345
出典データセット
uspto-grants-2013_08
特許番号
US08507536B2

反応ノート

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