Sodium Carbonate → ethyl 3-(4-nitrophenyl)-1H-indole-2-carboxylate

HRID 230543Notes

Reaction equation

HRID 230543 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[Li+].Br[C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][C:11]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20].[N+:24]([C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1)([O-:26])=[O:25]>C(O)C.C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N+:24]([C:27]1[CH:32]=[CH:31][C:30]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][C:11]=2[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:29][CH:28]=1)([O-:26])=[O:25]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 27735524-Nitrophenylboronic acidHCID 4715017Ethyl 3-Bromoindole-2-carboxylate

Product 1

HCID 12404967ethyl 3-(4-nitrophenyl)-1H-indole-2-carboxylateYield 88.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

46 ml of a 1M sodium carbonate solution, 2.23 g of lithium chloride and then 1.1 g of tetrakis(triphenylphosphine)palladium are added successively, under argon and with stirring, to a solution of 5 g of ethyl 3-bromo-1H-indole-2-carboxylate and 7.8 g of 4-nitrophenylboronic acid in 110 ml of ethanol and 110 ml of toluene. The solution is refluxed for 2 hours 30 minutes and then concentrated under reduced pressure. The precipitate is filtered off and then recrystallized from ethanol, to give 5.1 g of ethyl 3-(4-nitrophenyl)-1H-indole-2-carboxylate, the characteristics of which are as follows:

Workup

  1. temperatureThe solution is refluxed for 2 hours 30 minutes
  2. concentrationconcentrated under reduced pressure
  3. filtrationThe precipitate is filtered off
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-29229428bcbd4e8bb2c92168487decd3
Source dataset
uspto-grants-2009_07
Patent number
US07566736B2

Reaction notes

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