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

HRID 221924노트

반응식

HRID 221924 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 24193Titanium Tetrachloride촉매HCID 1140Toluene용매3회

실험 절차

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%).

후처리

  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))

출처 및 근거

ORD 기록
ord-d9e7895630f443b0b7e0e08e323f5a4f
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207134B2

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