Iodoethane → N-ethyl-6-trifluoromethyl-pyridine-3,4-diamine

HRID 895568Notes

Reaction equation

HRID 895568 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:7](I)[CH3:8].[F:10][C:11]([F:21])([F:20])[C:12]1[N:17]=[CH:16][C:15]([NH2:18])=[C:14]([NH2:19])[CH:13]=1>CN(C=O)C.CCOC(C)=O.O>[CH2:7]([NH:18][C:15]1[CH:16]=[N:17][C:12]([C:11]([F:10])([F:20])[F:21])=[CH:13][C:14]=1[NH2:19])[CH3:8]

Participants

7

Reactant 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 223800046-(Trifluoromethyl)pyridine-3,4-diamine

Product 1

HCID 22380096N-ethyl-6-trifluoromethyl-pyridine-3,4-diamine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Cesium carbonate (3.1 g, 26.88 mmol) and ethyl iodide (1.76 g, 10.75 mmol) is added to a solution of 6-trifluoromethyl-pyridine-3,4-diamine (1.05 g, 8.96 mmol) in anhydrous DMF (12 mL). The mixture is heated in a sealed tube for 18 h, then cooled to room temperature, and diluted with EtOAc and water. Usual work up and purification by column chromatography, eluting with EtOAc-hexanes provides pure N-Ethyl-6-trifluoromethyl-pyridine-3,4-diamine. 1H NMR (300 MHz, CDCl3): δ 7.95 (s, 1H); 6.95 (s, 1H), 3.21 (q, J=5.4 Hz, 2H), 1.35 (t, J=5.4 Hz, 3H).

Workup

  1. temperatureThe mixture is heated in a sealed tube for 18 h
  2. customUsual work up and purification by column chromatography
  3. washeluting with EtOAc-hexanes

Sources & evidence

ORD record
ord-09e0162e3d344cc6b51b086e03f78390
Source dataset
uspto-grants-2005_07
Patent number
US06916819B2

Reaction notes

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