Carbazole → HCID 67133322, compound

HRID 916158Notes

Reaction equation

HRID 916158 reaction equation
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]([F: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>[F:30][C:27]1[CH:28]=[CH:29][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:7]=[CH:8][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:10][CH:11]=2)[C:3]([OH:2])=[O:32])=[O:31])=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 6854CarbazoleHCID 14798Sodium HydroxideHCID 58960103HCID 58960103, compound

Product 1

HCID 67133322HCID 67133322, compoundYield 31,965.1%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 241BenzeneSolvent

Procedure

To a solution of 2-[(2-(4-fluorobenzoyl)phenyl)amino]-3-[4-(2-bromoethoxy)-phenyl]-propionic acid methyl ester (250 g, 0.50 mol) and carbazole (83.5 g, 0.50 mmol) in benzene (3000 ml) is added tetrabutyl ammonium bromide (80 g) and 40% NaOH aqueous solution (108 g, 1.08 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 (91.52 g, 32%).

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-b025b404052a41e9b695da30186dcf04
Source dataset
uspto-grants-2007_09
Patent number
US07268157B2

Reaction notes

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