N,N'-Dimethylethylenediamine → HCID 86650235, compound

HRID 2205751Notes

Reaction equation

HRID 2205751 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-fdd7751321e94c10862e04c513e449c3
Source dataset
uspto-grants-2016_06
Patent number
US09371329B2

Reaction notes

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