Chloroform → 2-{3-[N-(2-Methoxyethyl)-N-methylamino]-5-(6-phenylpyridin-3-yl)-4H-1,2,4-triazol-4-yl}benzonitrile

HRID 1797118Notes

Reaction equation

HRID 1797118 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[CH:14]=[N:15][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:17][CH:18]=2)=[N:11][N:10]=[C:9]1[N:25]([CH2:27][CH2:28][O:29][CH3:30])[CH3:26].[OH-].[Ca+2].[OH-].C(Cl)(Cl)Cl.[CH3:38][N:39]1CCCC1=O>[C-]#N.[Zn+2].[C-]#N>[CH3:30][O:29][CH2:28][CH2:27][N:25]([C:9]1[N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[C:38]#[N:39])[C:12]([C:13]2[CH:14]=[N:15][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:17][CH:18]=2)=[N:11][N:10]=1)[CH3:26]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 13387N-methyl-2-pyrrolidoneHCID 6093208Calcium HydroxideHCID 22019250[4-(2-Bromophenyl)-5-(6-phenylpyridin-3-yl)-4H-1,2,4-triazol-3-yl]-N-(2-methoxyethyl)-N-methylamine

Product 1

HCID 102950342-{3-[N-(2-Methoxyethyl)-N-methylamino]-5-(6-phenylpyridin-3-yl)-4H-1,2,4-triazol-4-yl}benzonitrileYield 63%

Reagents, catalysts & solvents 1

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst

Conditions

Temperature
180 °C

Procedure

[4-(2-Bromophenyl)-5-(6-phenylpyridin-3-yl)-4H-1,2,4-triazo 1-3-yl]-N-(2-methoxyethyl)-N-methylamine (436 mg) prepared in the Example 7 was dissolved in N-methyl-2-pyrrolidone (5 ml), followed by addition of zinc cyanide (121 mg), calcium hydroxide (76 mg) and tetrakis triphenylphosphine palladium (326 mg), and stirred at 180° C. for 3 hours. After the reaction solution was cooled to ambient temperature, chloroform was added to the solution, from which insoluble materials were filtered off. The filtrate was washed with saturated aqueous sodium hydrogen carbonate solution, and the organic layer was dried over anhydrous magnesium sulfate. After the solvent was evaporated under reduced pressure, the resulting solid was recrystallized from ethyl acetate, to afford the entitled compound as white crystal (242 mg, 63%). The physico-chemical values are as follows.

Workup

  1. temperatureAfter the reaction solution was cooled to ambient temperature
  2. filtrationwere filtered off
  3. washThe filtrate was washed with saturated aqueous sodium hydrogen carbonate solution
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. customAfter the solvent was evaporated under reduced pressure
  6. customthe resulting solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-8ab9f9aeac42425b9ffcfd227ea23a21
Source dataset
uspto-grants-2006_04
Patent number
US07034047B2

Reaction notes

Loading…