Carbazole → HCID 67133274, compound

HRID 916154Notes

Reaction equation

HRID 916154 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]=[N: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:7]=[CH:8][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:10][CH:11]=1)[C:3]([OH:2])=[O:31])(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[N:26][CH:25]=1

Participants

6

Reactant 3

HCID 6854CarbazoleHCID 14798Sodium HydroxideHCID 58960089HCID 58960089, compound

Product 1

HCID 67133274HCID 67133274, compoundYield 18.4%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 241BenzeneSolvent2×

Procedure

To a solution of 2-((2-nicotinoylphenyl)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 (0.05 g, 18%). HRMS calcd for C35H29N3O4: 555.6331. Found: 555.6329. MA calcd for C35H29N3O4: C, 75.66%; H, 5.26%; N, 7.56%. Found: C, 75.42%; H, 5.27%; N, 7.53%.

Workup

  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

Sources & evidence

ORD record
ord-e2a96441937c49118959ec7b025b89b0
Source dataset
uspto-grants-2007_09
Patent number
US07268157B2

Reaction notes

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