1-Chloromethylnaphthalene → 4-methoxy-2-methyl-1-[(1-naphthalenyl)methyl]-1H-indole

HRID 3358

반응식

HRID 3358 반응식
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[C:6]([CH3:12])[NH:7]2.[H-].[Na+].Cl[CH2:16][C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1>CN(C=O)C.O>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[C:6]([CH3:12])[N:7]2[CH2:16][C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1

참가 물질

6

반응물 3

HCID 68451-ChloromethylnaphthaleneHCID 24758Sodium hydrideHCID 107732744-methoxy-2-methyl-1H-indole

생성물 1

HCID 106380394-methoxy-2-methyl-1-[(1-naphthalenyl)methyl]-1H-indole수율 97.1%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

4-Methoxy-2-methyl-1H-indole (644 mg, 4 mmol) was dissolved in 10 mL of DMF and 160 mg (4 mmol) of 60% NaH/mineral oil was added. After 0.67 hours, 707 mg (4 mmol) of 1-(chloromethyl)naphthalene was added. After 5 hours, the mixture was diluted with water and extracted twice with ethyl acetate. The combined ethyl acetate was washed with brine, dried (MgSO4) and concentrated at reduced pressure. The residue was chromatographed on silica gel and eluted with 20% EtOAc/hexane to give 1.17 g (97% yield) of 4-methoxy-2-methyl-1-[(1-naphthalenyl)methyl]-1H-indole.

후처리

  1. waitAfter 5 hours
  2. extractionextracted twice with ethyl acetate
  3. washThe combined ethyl acetate was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated at reduced pressure
  6. customThe residue was chromatographed on silica gel
  7. washeluted with 20% EtOAc/hexane

출처 및 근거

ORD 기록
ord-80c7b751a3284a8b966f0ea7134ae600
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05733923

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