Carbazole → HCID 67133134, compound

HRID 916156Notes

Reaction equation

HRID 916156 reaction equation
C[O:2][C:3](=[O:31])[CH:4]([NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23](=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[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:32]1[C:44]2[NH:43][C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[C:36]=2[CH:35]=[CH:34][CH:33]=1.[OH-].[Na+]>C1C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:23]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[NH:16][CH:4]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][C:41]2[C:42]3[NH:43][C:44]4[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=4)[C:37]=3[CH:38]=[CH:39][CH:40]=2)=[CH:8][CH:7]=1)[C:3]([OH:2])=[O:31])(=[O:30])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 3

HCID 6854CarbazoleHCID 14798Sodium HydroxideHCID 58960092HCID 58960092, compound

Product 1

HCID 67133134HCID 67133134, compoundYield 28.7%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 241BenzeneSolvent

Procedure

To a solution of 2-((2-benzoylphenyl)amino)-3-[4-(2-bromoethoxy)-phenyl]-propionic acid methyl ester (240 g, 0.49 mol) and carbazole (82 g, 0.49 mol) in benzene (3000 ml) is added tetrabutyl ammonium bromide (80 g) and 40% NaOH aqueous solution (105 g, 1.05 mol), then the mixture is heated to reflux for 10 h. After cooled, the upper organic layer is evaporated under a vacuum. The crude product is purified by silica gel chromatography using CHCl3/MeOH (8:1) as eluent to give the title compound (78 g, 28.7%).

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 10 h
  3. temperatureAfter cooled
  4. customthe upper organic layer is evaporated under a vacuum
  5. customThe crude product is purified by silica gel chromatography

Sources & evidence

ORD record
ord-a83d75dff0b549f189ccae59a2debab8
Source dataset
uspto-grants-2007_09
Patent number
US07268157B2

Reaction notes

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