N,N'-Dimethylethylenediamine → HCID 86650235, compound

HRID 406446Notes

Reaction equation

HRID 406446 reaction equation
Br[C:2]1[N:3]=[C:4]([C:22]([F:25])([F:24])[F:23])[N:5]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=3)[CH:8]=[CH:7][C:6]=12.[C-]#N.[Na+].[CH3:29][NH:30]CCNC>C1(C)C=CC=CC=1.[Cu]I>[F:19][C:18]([F:21])([F:20])[O:17][C:14]1[CH:15]=[CH:16][C:11]([C:9]2[CH:8]=[CH:7][C:6]3[N:5]([C:4]([C:22]([F:24])([F:23])[F:25])=[N:3][C:2]=3[C:29]#[N:30])[CH:10]=2)=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 8070N,N'-DimethylethylenediamineHCID 8929Sodium CyanideHCID 86650234HCID 86650234, compound

Product 1

HCID 86650235HCID 86650235, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
130 °C

Procedure

1-bromo-6-(4-(trifluoromethoxy)phenyl)-3-(trifluoromethyl)imidazo[1,5-a]pyridine (50.0 mg, 0.118 mmol), NaCN (7.0 mg, 0.142 mmol, 1.2 equiv.), CuI (2.2 mg, 0.0118 mmol, 0.1 equiv.) and KI (3.9 mg, 0.0236 mmol, 0.2 equiv.) were successively placed in a 5 mL Samith vial. To the vial was added a solution of N,N′-dimethylethylenediamine (10.4 mg, 0.118 mmol, 1.0 equiv.) in toluene (5 mL). The suspension was heated by the microwave reactor (Biotage, Personal Chemistry) at 130° C. for 60 min. The suspension was filtered through Celite (3 g) using EtOAc (70 mL). The solvent was removed from the filtrate under a reduced pressure to give a crude mixture. The crude mixture was purified by a preparative TLC (SiO2=1 plate, EtOAc/hexane=1:7 Rf=0.1) to give 6-(4-(trifluoromethoxy)phenyl)-3-(trifluoromethyl)imidazo[1,5-a]pyridine-1-carbonitrile as colorless crystals.

Workup

  1. filtrationThe suspension was filtered through Celite (3 g)
  2. customThe solvent was removed from the filtrate under a reduced pressure
  3. customto give a crude mixture
  4. customThe crude mixture was purified by a preparative TLC (SiO2=1 plate, EtOAc/hexane=1:7 Rf=0.1)

Sources & evidence

ORD record
ord-daf69047d2184186982729f6fc6f295a
Source dataset
uspto-grants-2014_06
Patent number
US08754103B2

Reaction notes

Loading…