Dimethyl Sulfoxide → 5-Chloro-7-methyl-1-tosyl-1H-indole-4-carbaldehyde

HRID 2173970노트

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HRID 2173970 반응식
[Cl:1][C:2]1[C:3]([CH2:22][OH:23])=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[N:7]([S:12]([C:15]1[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:6]=[CH:5]2.C(N(C(C)C)C(C)C)C.CS(C)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:8]2[N:7]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[CH:6]=[CH:5][C:4]=2[C:3]=1[CH:22]=[O:23]

참가 물질

5

반응물 3

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 86701537(5-Chloro-7-methyl-1-tosyl-1H-indol-4-yl)methanol

생성물 1

HCID 867015395-Chloro-7-methyl-1-tosyl-1H-indole-4-carbaldehyde

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To a solution of (5-chloro-7-methyl-1-tosyl-1H-indol-4-yl)methanol (3.3 g, 9.5 mmol) and N-ethyl-diisopropylamine (8.3 mL, 47.3 mmol) in CH2Cl2 (20 mL)/DMSO (1 mL) was added SO3.Py (4.5 g, 28.4 mmol) at 0° C. The mixture was stirred at 0° C. for 2.5 h, and then stirred at room temperature for 15 h. The reaction was quenched by MeOH. The mixture was stirred for 1 h. The mixture was partially concentrated. The mixture was diluted with H2O, and then the resulted solid was collected by filtration. The resulting residue was triturated with MeOH to give the title compound. 1H NMR (400 MHz, ACETONITRILE-d3) δ 10.56 (s, 1H), 8.00 (d, J=3.80 Hz, 1H), 7.62 (d, J=3.80 Hz, 1H), 7.60 (d, J=8.60 Hz, 2H), 7.35 (d, J=8.60 Hz, 2H), 7.22 (s, 1H), 2.60 (s, 3H), 2.37 (s, 3H).

후처리

  1. stirringstirred at room temperature for 15 h
  2. customThe reaction was quenched by MeOH
  3. stirringThe mixture was stirred for 1 h
  4. concentrationThe mixture was partially concentrated
  5. additionThe mixture was diluted with H2O
  6. filtrationthe resulted solid was collected by filtration
  7. customThe resulting residue was triturated with MeOH

출처 및 근거

ORD 기록
ord-1b97057e36da46349d4921b5ea1ec617
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09056874B2

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