Hexane → 1-[(4-fluorophenyl)methyl]-4-methoxy-2-methyl-1H-indole

HRID 581131

반응식

HRID 581131 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+].CCCCCC.[F:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Cl)=[CH:24][CH:23]=1>CN(C=O)C.O>[F:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][N:7]2[C:8]3[C:4](=[C:3]([O:2][CH3:1])[CH:11]=[CH:10][CH:9]=3)[CH:5]=[C:6]2[CH3:12])=[CH:24][CH:23]=1

참가 물질

7

반응물 4

HCID 8058HexaneHCID 96024-Fluorobenzyl chlorideHCID 24758Sodium hydrideHCID 107732744-methoxy-2-methyl-1H-indole

생성물 1

HCID 108258491-[(4-fluorophenyl)methyl]-4-methoxy-2-methyl-1H-indole수율 84%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

실험 절차

4-Methoxy-2-methyl-1H-indole (805 mg, 5 mmol) was added to a mixture of 200 mg (5 mmol) of 60% sodium hydride/mineral oil (washed with hexane before adding DMF) in 10 mL of DMF and after stirring for 0.5 hours, 0.6 mL (5 mmol) of 4-fluorobenzyl chloride was added. The mixture was stirred at room temperature for 18 hours, diluted with water and extracted with ethyl acetate. The ethyl acetate solution was washed with brine, dried (MgSO4) and after concentrating at reduced pressure, the residue was chromatographed on silica gel eluting with 20% EtOAc/hexane to give 1.1 g (84% yield) of 1-[(4-fluorophenyl)methyl]-4-methoxy-2-methyl-1H-indole, melting at 104-108° C.

후처리

  1. stirringThe mixture was stirred at room temperature for 18 hours
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate solution was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationafter concentrating at reduced pressure
  6. customthe residue was chromatographed on silica gel eluting with 20% EtOAc/hexane

출처 및 근거

ORD 기록
ord-414cccc833ac4dcb8745540f08f47291
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05919810

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