Toluene → methyl 2-[2-methyl-1-(4-nitrobenzyl)-1H-indol-3-yl]acetate

HRID 589332Notes

Reaction equation

HRID 589332 reaction equation
C1(C)C=CC=CC=1.[CH3:8][C:9]1[NH:10][C:11]2[C:16]([C:17]=1[CH2:18][C:19]([O:21][CH3:22])=[O:20])=[CH:15][CH:14]=[CH:13][CH:12]=2.[N+:23]([C:26]1[CH:33]=[CH:32][C:29]([CH2:30]Br)=[CH:28][CH:27]=1)([O-:25])=[O:24].C(=O)([O-])[O-].[Cs+].[Cs+]>[Br-].C([P+](CCCC)(CCCC)CCCC)CCCCCCCCCCCCCCC.O>[CH3:8][C:9]1[N:10]([CH2:30][C:29]2[CH:32]=[CH:33][C:26]([N+:23]([O-:25])=[O:24])=[CH:27][CH:28]=2)[C:11]2[C:16]([C:17]=1[CH2:18][C:19]([O:21][CH3:22])=[O:20])=[CH:15][CH:14]=[CH:13][CH:12]=2

Participants

7

Reactant 4

HCID 1140TolueneHCID 10796Cesium carbonateHCID 660114-Nitrobenzyl bromideHCID 10774509Sbb044946

Product 1

HCID 89590250methyl 2-[2-methyl-1-(4-nitrobenzyl)-1H-indol-3-yl]acetateYield 3.7%

Reagents, catalysts & solvents 2

HCID 84716Hexadecyltributylphosphonium bromideCatalystHCID 962WaterSolvent

Procedure

Into 100 mL toluene were added methyl 2-(2-methyl-1H-indol-3-yl)acetate (4.9 g, 24.1 mmol), p-nitro benzyl bromide (5.18 g, 24.0 mmol), cesium carbonate (9.38 g, 28.8 mmol), and cetyl tributyl phosphonium bromide (1.58 g, 3.1 mmol). Upon completion of addition, it was reacted at 110° C. for 6 hours. Upon completion of the reaction, it was cooled, water was added, and extracted with diethyl ether. The extract was washed with water. The organic phase was rotate evaporated to dryness, and purified by preparative liquid phase to obtain the product 300 mg, at a yield of 3.7%.

Workup

  1. additionUpon completion of addition, it
  2. customwas reacted at 110° C. for 6 hours
  3. customUpon completion of the reaction, it
  4. temperaturewas cooled
  5. extractionextracted with diethyl ether
  6. washThe extract was washed with water
  7. customThe organic phase was rotate evaporated to dryness
  8. custompurified by preparative liquid phase

Sources & evidence

ORD record
ord-6b0a7c77c1b04060bd0ac9cdcaf89dd8
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

Loading…