Pyridine → 3-fluoro-N-[3-(4,4,6-trimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenyl]-benzenesulfonamide

HRID 1036954ノート

反応式

HRID 1036954 の反応式
[CH3:1][C:2]1([CH3:20])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=2)[NH:5][CH:4]([C:13]2[CH:14]=[C:15]([NH2:19])[CH:16]=[CH:17][CH:18]=2)[CH2:3]1.N1C=CC=CC=1.[F:27][C:28]1[CH:29]=[C:30]([S:34](Cl)(=[O:36])=[O:35])[CH:31]=[CH:32][CH:33]=1>ClCCl>[F:27][C:28]1[CH:29]=[C:30]([S:34]([NH:19][C:15]2[CH:16]=[CH:17][CH:18]=[C:13]([CH:4]3[CH2:3][C:2]([CH3:20])([CH3:1])[C:11]4[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=4)[NH:5]3)[CH:14]=2)(=[O:36])=[O:35])[CH:31]=[CH:32][CH:33]=1

参加物

5

反応物 3

HCID 1049PyridineHCID 27342583-Fluorobenzenesulfonyl ChlorideHCID 672908283-(4,4,6-Trimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenylamine

生成物 1

HCID 569662053-fluoro-N-[3-(4,4,6-trimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenyl]-benzenesulfonamide収率 38%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

To a stirred mixture of 3-(4,4,6-trimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenylamine (135 mg, 0.5 mmol) in dichloromethane (3 mL) was added pyridine (60 mg, 0.75 mmol) in dichloromethane (2 mL) and 3-fluoro-benzenesulfonyl chloride (108 mg, 0.56 mmol) under nitrogen. The resultant mixture was stirred for 4 h. The reaction mixture was diluted with dichloromethane, washed with water (twice), saturated brine, and dried over magnesium sulfate. Magnesium sulfate was removed by filtration, and after evaporation, the residue was purified on chromatography column (silica gel, petroleum ether: Ethyl acetate=12:1) to afford 80 mg of 3-fluoro-N-[3-(4,4,6-trimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenyl]-benzenesulfonamide as yellow solid (Yield: 38%). MS (ESI+APCI) M+1=425.2.

後処理

  1. washwashed with water (twice), saturated brine
  2. dry with materialdried over magnesium sulfate
  3. customMagnesium sulfate was removed by filtration
  4. customafter evaporation
  5. customthe residue was purified on chromatography column (silica gel, petroleum ether: Ethyl acetate=12:1)

出典と根拠

ORDレコード
ord-597806d5e319410bbf3ab96daf37cb52
出典データセット
uspto-grants-2013_10
特許番号
US08546427B2

反応ノート

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