1-Bromo-4-nitrobenzene → 5-(4-tert-Butylphenyl)-1-(4-nitrophenyl)indole-2-carboxylic acid ethyl ester

HRID 646120Notes

Reaction equation

HRID 646120 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([C:15]1[CH:20]=[CH:19][C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:17][CH:16]=1)=[CH:10][CH:9]=2)=[O:5])[CH3:2].Br[C:26]1[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=1.[OH-].[Na+:36]>O1CCOCC1>[CH2:1]([O:3][C:4]([C:6]1[N:7]([C:26]2[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([C:15]1[CH:16]=[CH:17][C:18]([C:21]([CH3:23])([CH3:22])[CH3:24])=[CH:19][CH:20]=1)=[CH:10][CH:9]=2)=[O:5])[CH3:2].[C:21]([C:18]1[CH:17]=[CH:16][C:15]([C:11]2[CH:12]=[C:13]3[C:8](=[CH:9][CH:10]=2)[N:7]([C:26]2[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=2)[C:6]([C:4]([O-:3])=[O:5])=[CH:14]3)=[CH:20][CH:19]=1)([CH3:24])([CH3:23])[CH3:22].[Na+:36]

Participants

6

Reactant 3

HCID 114661-Bromo-4-nitrobenzeneHCID 14798Sodium HydroxideHCID 68475095Ethyl 5-(4-(tert-butyl)phenyl)-1H-indole-2-carboxylate

Product 2

HCID 686950695-(4-tert-Butylphenyl)-1-(4-nitrophenyl)indole-2-carboxylic acid ethyl esterHCID 68701941Sodium 5-(4-tert-butylphenyl)-1-(4-nitrophenyl)indole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5-(4-tert-Butylphenyl)-1-(4-nitrophenyl)indole-2-carboxylic acid ethyl ester was prepared in accordance with Example 1 using 5-(4-tert-butylphenyl)indole-2-carboxylic acid ethyl ester and 1-bromo-4-nitrobenzene. This ester (207 mg, 0.47 mmol) was dissolved in dioxane (2 mL) to which aqueous NaOH (1M, 1 mL) was added. The mixture was heated using microwave irradiation at 120° C. for 15 min and allowed to cool. The precipitate was filtered off, washed with water and recrystallised from EtOH/EtOAc to yield the title compound.

Workup

  1. additionwas added
  2. temperatureThe mixture was heated
  3. custommicrowave irradiation at 120° C. for 15 min
  4. temperatureto cool
  5. filtrationThe precipitate was filtered off
  6. washwashed with water
  7. customrecrystallised from EtOH/EtOAc

Sources & evidence

ORD record
ord-6189d39c193b4266b377ce637ba4368b
Source dataset
uspto-grants-2010_04
Patent number
US07705023B2

Reaction notes

Loading…