N,N-Dimethylpropargylamine → HCID 21959479, compound

HRID 887580Notes

Reaction equation

HRID 887580 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1)[NH2:5].[CH3:13][N:14]([CH3:18])[CH2:15][C:16]#[CH:17]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[NH2:5][C:4]1[CH:3]=[C:2]([CH2:17][C:16]#[C:15][N:14]([CH3:18])[CH3:13])[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=1

Participants

5

Reactant 2

HCID 81643N,N-DimethylpropargylamineHCID 27358803-Bromo-5-(trifluoromethyl)aniline

Product 1

HCID 21959479HCID 21959479, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalyst

Conditions

Temperature
100 °C

Procedure

A mixture of 3-bromo-5-trifluoromethylaniline (1.4 g, 5.9 mmol), 1-dimethylamino-2-propyne (1.3 mL, 0.76 mmol), PdCl2(PPh3)2 (0.26 g, 0.29 mmol) and CuI (114 mg, 0.60 mmol) in 10 mL of TEA was heated at 100° C. in a sealed tube for 3 h. The resulting mixture was filtered over Celite®. The filtrate was concentrated, and the residue was purified by prep-HPLC (reverse phase) to give the aniline. MS (ES+): 243 (M+H)+; (ES−): 241 (M−H)−. Calc'd C12H13F3N2—242.24.

Workup

  1. filtrationThe resulting mixture was filtered over Celite®
  2. concentrationThe filtrate was concentrated
  3. customthe residue was purified by prep-HPLC (reverse phase)

Sources & evidence

ORD record
ord-1a5030451ced486c8fbca6738b77e504
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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