Water → 5-(2,6-Diethyl-Phenyl)-1-(2,5-Dimethyl-Benzyl)-1H-Pyrrolo[2,3-C]Pyridine

HRID 472025노트

반응식

HRID 472025 반응식
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[C:11]1[CH:12]=[C:13]2[CH:19]=[CH:18][NH:17][C:14]2=[CH:15][N:16]=1)[CH3:2].[H-].[Na+].Cl[CH2:23][C:24]1[CH:29]=[C:28]([CH:30](C)C)[CH:27]=[CH:26][C:25]=1[CH3:33].O>CN(C=O)C.CCOC(C)=O>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[C:11]1[CH:12]=[C:13]2[CH:19]=[CH:18][N:17]([CH2:23][C:24]3[CH:29]=[C:28]([CH3:30])[CH:27]=[CH:26][C:25]=3[CH3:33])[C:14]2=[CH:15][N:16]=1)[CH3:2]

참가 물질

7

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 116732465-(2,6-diethyl-phenyl)-1H-pyrrolo[2,3-c]pyridineHCID 205360412-(Chloromethyl)-1-methyl-4-(propan-2-yl)benzene

생성물 1

HCID 671524665-(2,6-Diethyl-Phenyl)-1-(2,5-Dimethyl-Benzyl)-1H-Pyrrolo[2,3-C]Pyridine

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 5-(2,6-diethyl-phenyl)-1H-pyrrolo[2,3-c]pyridine (15 mg, 0.06 mmol) in DMF (0.5 mL) is added NaH (95%, 4 mg). The reaction mixture is stirred at room temperature for 30 minutes, and 2-chloromethyl-4-isopropyl-1-methyl-benzene (33 mg, 0.18 mmol) is then added. The mixture is heated at 60° C. for three hours and cooled. To the mixture, water (2 ml) and EtOAc (2 mL) are added. The organic layer is separated, washed with water once and concentrated under reduced pressure. The residue is purified by PTLC (Hexane/EtOAc 4:1) to give the titled compound. 1H NMR: (CDCl3) 8.81 (s, 1H), 7.47 (s, 1H), 7.28 (t, 1H), 7.13-7.19 (m, 5H), 6.77 (s, 1H), 6.52 (d, 1H), 5.39 (s, 2H), 2.80 (m, 1H), 2.27-2.40 (m, 7H), 1.14 (d, 2H), 1.01 (t, 6H).

후처리

  1. temperatureThe mixture is heated at 60° C. for three hours
  2. temperaturecooled
  3. customThe organic layer is separated
  4. washwashed with water once
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by PTLC (Hexane/EtOAc 4:1)

출처 및 근거

ORD 기록
ord-ac23960870c541a38bb03f90ce6ea927
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633193B2

반응 노트

불러오는 중…