Carbazole → HCID 67133322, compound

HRID 916151Notes

Reaction equation

HRID 916151 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 36%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 241BenzeneSolvent2×

Procedure

To a solution of 2-[(2-(4-fluorobenzoyl)phenyl)amino]-3-[4-(2-bromoethoxy)-phenyl]-propionic acid methyl ester (0.25 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 (0.10 g, 36%). HRMS calcd for C36H29FN2O4: 572.6357. Found: 572.6354. MA calcd for C36H29FN2O4: C, 75.51%; H, 5.11%; N, 4.89%. Found: C, 75.83%; H, 5.10%; N, 4.90%.

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-3f103cb24af34155b2b062f95fd5e59c
Source dataset
uspto-grants-2007_09
Patent number
US07268157B2

Reaction notes

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