Carbazole → HCID 67133432, 화합물

HRID 916164노트

반응식

HRID 916164 반응식
C[O:2][C:3](=[O:32])[CH:4]([NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23](=[O:31])[C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14]Br)=[CH:8][CH:7]=1.[CH:33]1[C:45]2[NH:44][C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:37]=2[CH:36]=[CH:35][CH:34]=1.[OH-].[Na+]>C1C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:30][C:27]1[CH:26]=[CH:25][C:24]([C:23]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[NH:16][CH:4]([CH2:5][C:6]2[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][C:42]3[C:43]4[NH:44][C:45]5[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=5)[C:38]=4[CH:39]=[CH:40][CH:41]=3)=[CH:8][CH:7]=2)[C:3]([OH:2])=[O:32])=[O:31])=[CH:29][CH:28]=1

참가 물질

6

반응물 3

HCID 6854CarbazoleHCID 14798Sodium HydroxideHCID 58960086HCID 58960086, 화합물

생성물 1

HCID 67133432HCID 67133432, 화합물수율 54%

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 241Benzene용매2회

실험 절차

To a solution of 2-[(2-(4-methylbenzoyl)phenyl)amino]-3-[4-(2-bromoethoxy)-phenyl]-propionic acid methyl ester (0.24 g, 0.49 mmol) and carbazole (0.082 g, 0.49 mmol) in benzene (10 ml) is added tetrabutyl ammonium bromide (0.08 g) and 50% NaOH aqueous solution (0.084 g, 1.08 mmol), then the mixture is heated to reflux for 10 h. After cooled, benzene (30 ml) is added, and the mixture is washed with water (3×30 ml). Then the solvent is evaporated under a vacuum. The crude product is purified by silica gel chromatography using CHCl3/MeOH (4:1) as eluent to give the title compound (0.15 g, 54%). HRMS calcd for C37H32N2O4: 568.6692. Found: 568.6693. MA calcd for C37H32N2O4: C, 78.15%; H, 5.67%; N, 4.93%. Found: C, 78.36%; H, 5.64%; N, 4.91%.

후처리

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 10 h
  3. temperatureAfter cooled
  4. washthe mixture is washed with water (3×30 ml)
  5. customThen the solvent is evaporated under a vacuum
  6. customThe crude product is purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-b510584dbb6a439889fa78739707df16
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07268157B2

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