Carbazole → 2-[1-Methyl-3-oxo-3-(4-fluorophenyl)-propenylamino]-3-[4-(2-carbazolylethoxy)-phenyl]-propionic acid

HRID 916142Notes

Reaction equation

HRID 916142 reaction equation
C[O:2][C:3](=[O:29])[CH:4]([NH:16][C:17]([CH3:28])=[CH:18][C:19](=[O:27])[C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=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:30]1[C:42]2[NH:41][C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:34]=2[CH:33]=[CH:32][CH:31]=1.[OH-].[Na+]>C1C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:28][C:17]([NH:16][CH:4]([CH2:5][C:6]1[CH:7]=[CH:8][C:9]([O:12][CH2:13][CH2:14][C:39]2[C:40]3[NH:41][C:42]4[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=4)[C:35]=3[CH:36]=[CH:37][CH:38]=2)=[CH:10][CH:11]=1)[C:3]([OH:2])=[O:29])=[CH:18][C:19](=[O:27])[C:20]1[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 6854CarbazoleHCID 14798Sodium HydroxideHCID 671331222-[1-Methyl-3-oxo-3-(4-fluorophenyl)-propenylamino]-3-[4-(2-bromoethoxy)-phenyl]-propionic acid methyl ester

Product 1

HCID 671332842-[1-Methyl-3-oxo-3-(4-fluorophenyl)-propenylamino]-3-[4-(2-carbazolylethoxy)-phenyl]-propionic acidYield 23%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 241BenzeneSolvent2×

Procedure

To a solution of 2-[1-methyl-3-oxo-3-(4-fluorophenyl)-propenylamino]-3-[4-(2-bromoethoxy)-phenyl]-propionic acid methyl ester (0.23 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 (0.06 g, 23%). HRMS calcd for C33H29FN2O4: 536.6027. Found: 536.6025. MA calcd for C33H29FN2O4: C, 73.86%; H, 5.45%; N, 5.22%. Found: C, 73.63%; H, 5.46%; N, 5.20%.

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-087a5fef477143d9baba83fc322deefb
Source dataset
uspto-grants-2007_09
Patent number
US07268157B2

Reaction notes

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