Sodium hydride → Benzyl 3-[7-bromo-1-(3-methoxypropyl)-3-methyl-1H-indol-6-yl methoxy]-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

HRID 1176245

반응식

HRID 1176245 반응식
[Br:1][C:2]1[C:3]([CH2:12][O:13][CH:14]2[CH:19]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH2:29][O:30][CH2:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=4[O:38][CH3:39])=[CH:22][CH:21]=3)[CH2:18][CH2:17][N:16]([C:40]([O:42][CH2:43][C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)=[O:41])[CH2:15]2)=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[CH3:11].[H-].[Na+].Cl[CH2:53][CH2:54][CH2:55][O:56][CH3:57].C(=O)([O-])O.[Na+]>CN(C)C=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:1][C:2]1[C:3]([CH2:12][O:13][CH:14]2[CH:19]([C:20]3[CH:21]=[CH:22][C:23]([O:26][CH2:27][CH2:28][CH2:29][O:30][CH2:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=4[O:38][CH3:39])=[CH:24][CH:25]=3)[CH2:18][CH2:17][N:16]([C:40]([O:42][CH2:43][C:44]3[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=3)=[O:41])[CH2:15]2)=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:53][CH2:54][CH2:55][O:56][CH3:57])[CH:8]=[C:7]2[CH3:11]

참가 물질

7

반응물 4

HCID 24758Sodium hydrideHCID 1189271-Chloro-3-methoxypropaneHCID 516892Sodium BicarbonateHCID 68499829benzyl 3-(7-bromo-3-methyl-1H-indol-6-ylmethoxy)-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

생성물 1

HCID 68501531Benzyl 3-[7-bromo-1-(3-methoxypropyl)-3-methyl-1H-indol-6-yl methoxy]-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 6228Dimethylformamide용매

실험 절차

The solution of 0.208 g benzyl 3-(7-bromo-3-methyl-1H-indol-6-ylmethoxy)-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate in 2.0 ml of N,N-dimethylformamide is cooled to 0° C., admixed with 0.023 g of sodium hydride dispersion (60%) and stirred over 10 minutes. The mixture is admixed successively with 0.126 ml of 1-chloro-3-methoxypropane and 0.011 g of tetrabutylammonium iodide and subsequently stirred at room temperature over 18 h. The reaction mixture is poured onto 1M sodium hydrogencarbonate solution (30 ml) and extracted with tert-butyl methyl ether (2×30 ml). The organic phases are washed with water (30 ml) and brine (30 ml), dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a slightly yellowish oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.17 (1:2 EtOAc-heptane); Rt=6.60.

후처리

  1. stirringsubsequently stirred at room temperature over 18 h
  2. extractionextracted with tert-butyl methyl ether (2×30 ml)
  3. washThe organic phases are washed with water (30 ml) and brine (30 ml)
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated by evaporation

출처 및 근거

ORD 기록
ord-b76631f08b6945a2a6dca75089acafec
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842688B2

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