Cesium carbonate → N-ethyl-5-(furan-3-yl)-2-methylaniline

HRID 1964015

Reaction equation

HRID 1964015 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[NH:7][CH2:8][CH3:9].[O:12]1[CH:16]=[CH:15][C:14](B2OC(C)(C)C(C)(C)O2)=[CH:13]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1>[CH2:8]([NH:7][C:6]1[CH:10]=[C:2]([C:14]2[CH:15]=[CH:16][O:12][CH:13]=2)[CH:3]=[CH:4][C:5]=1[CH3:11])[CH3:9]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27739962-(Furan-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 437296995-bromo-N-ethyl-2-methylaniline

Product 1

HCID 66877311N-ethyl-5-(furan-3-yl)-2-methylanilineYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.69 g (3.20 mmol) of 5-bromo-N-ethyl-2-methylaniline and 0.93 g (4.80 mmol) of 3-furan boronic acid pinacol ester were dissolved in 7 mL of THF. 1.56 g (4.80 mmol) of cesium carbonate and 370 mg (0.32 mmol) of tetrakis(triphenyl phosphine)palladium(0) were added thereto and heated under reflux for 22 hours. After completion of the reaction, filtration was conducted, and the filtrate was condensed. The resulting crude product was separated and purified using silica gel column chromatography to give N-ethyl-5-(furan-3-yl)-2-methylaniline (yield: 98%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 22 hours
  3. customAfter completion of the reaction, filtration
  4. customcondensed
  5. customThe resulting crude product was separated
  6. custompurified

Sources & evidence

ORD record
ord-6f317208b33b4f2a8539517b604f631b
Source dataset
uspto-grants-2013_04
Patent number
US08415479B2

Linked notes

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