Water → 1-(Benzenesulfonyl)-1H-indol-5-amine

HRID 84200

반응식

HRID 84200 반응식
COC([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15])[CH:9]=[CH:8]2)=O.O.[Cl-].[NH4+:25]>C(Cl)Cl.[Fe]>[C:17]1([S:14]([N:10]2[C:11]3[C:7](=[CH:6][C:5]([NH2:25])=[CH:13][CH:12]=3)[CH:8]=[CH:9]2)(=[O:16])=[O:15])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

참가 물질

6

반응물 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 575174331H-Indole-5-carboxylic acid, 1-(phenylsulfonyl)-, methyl ester

생성물 1

HCID 154501451-(Benzenesulfonyl)-1H-indol-5-amine수율 82.2%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 6344Dichloromethane용매

실험 절차

To the suspension of 2 (1.16 g, 3.84 mmol) in WA (38 mL) and water (9 mL), iron (0.64 g, 11.51 mmol) and ammonium chloride (0.41 g, 7.67 mmol) were added and refluxed overnight. After the reaction was filtrated with celite, the solvent was concentrated under reduced pressure to give a brown residue, which was dissolved in CH2Cl2 and quenched with water, followed by extracted with CH2Cl2 (20 mL×3). The combined organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure to give a brown residue, which was purified by silica gel chromatography (EtOAc:n-hexane=1:2:1% NH3(aq)) to afford 27 (0.86 g). 1H NMR (500 MHz, CD3OD): δ 3.60 (s, 2H), 6.48 (d, J=3.6 Hz, 1H), 6.69 (dd, J=8.7, 2.1 Hz, 1H), 6.76 (d, J=1.8 Hz, 1H), 7.39-7.42 (m, 2H), 7.44 (d, J=3.5 Hz, 1H), 7.49-7.51 (m, 1H), 7.77 (d, J=8.7 Hz, 1H), 7.82 (d, J=7.9 Hz, 2H).

후처리

  1. additionwere added
  2. temperaturerefluxed overnight
  3. filtrationAfter the reaction was filtrated with celite
  4. concentrationthe solvent was concentrated under reduced pressure
  5. customto give a brown residue, which
  6. customquenched with water
  7. extractionby extracted with CH2Cl2 (20 mL×3)
  8. dry with materialThe combined organic layer was dried over anhydrous MgSO4
  9. concentrationconcentrated under reduced pressure
  10. customto give a brown residue, which
  11. customwas purified by silica gel chromatography (EtOAc:n-hexane=1:2:1% NH3(aq))

출처 및 근거

ORD 기록
ord-b80ae43d1fab46a897ece91672d172cb
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846748B2

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