Sodium Bicarbonate → 1-benzenesulfonyl-6-bromo-5-methyl-1H-indole

HRID 221924ノート

反応式

HRID 221924 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([N:9]([CH2:19][CH:20](OCC)OCC)[S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH:5]=[CH:6][C:7]=1[CH3:8].C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.[Ti](Cl)(Cl)(Cl)Cl>[C:13]1([S:10]([N:9]2[C:4]3[C:5](=[CH:6][C:7]([CH3:8])=[C:2]([Br:1])[CH:3]=3)[CH:20]=[CH:19]2)(=[O:11])=[O:12])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参加物

5

反応物 2

HCID 516892Sodium BicarbonateHCID 59488771N-(3-bromo-4-methylphenyl)-N-(2,2-diethoxyethyl)benzenesulfonamide

生成物 1

HCID 594888191-benzenesulfonyl-6-bromo-5-methyl-1H-indole収率 50%

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒HCID 1140Toluene溶媒3 回

実験手順

Under a nitrogen stream, a solution of N-(3-bromo-4-methylphenyl)-N-(2,2-diethoxyethyl)benzenesulfonamide (5.16 g, 11.66 mmol) in toluene (118 mL) and a solution of titanium tetrachloride (1.92 mL, 17.51 mmol) in toluene (118 mL) were simultaneously added dropwise over 25 minutes to toluene (315 mL) which was heated to reflux. After heating to reflux for 1 hour, the reaction mixture was cooled to room temperature and then saturated aqueous sodium hydrogen carbonate was added thereto. The resultant mixture was extracted with ethyl acetate. After drying (anhydrous potassium carbonate), solvent was removed by distillation under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solution=ethyl acetate:n-hexane (1:4)), to thereby obtain the titled compound (2.04 g, 50%).

後処理

  1. temperaturewas heated to reflux
  2. temperatureAfter heating
  3. temperatureto reflux for 1 hour
  4. extractionThe resultant mixture was extracted with ethyl acetate
  5. dry with materialAfter drying (anhydrous potassium carbonate), solvent
  6. customwas removed by distillation under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (developing solution=ethyl acetate:n-hexane (1:4))

出典と根拠

ORDレコード
ord-d9e7895630f443b0b7e0e08e323f5a4f
出典データセット
uspto-grants-2012_06
特許番号
US08207134B2

反応ノート

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