Ethyl orthoformate → 6-(4-Ethoxy-3-(trifluoromethyl)phenyl)-3H-imidazo[4,5-c]pyridine-4-carbonitrile

HRID 2246431Notes

Reaction equation

HRID 2246431 reaction equation
[NH2:1][C:2]1[C:3]([C:22]#[N:23])=[N:4][C:5]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH3:17])=[C:11]([C:18]([F:21])([F:20])[F:19])[CH:10]=2)=[CH:6][C:7]=1[NH2:8].[CH2:24](OC(OCC)OCC)C>[O-]S(C(F)(F)F)(=O)=O.[Yb+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O.C(#N)C>[CH2:16]([O:15][C:12]1[CH:13]=[CH:14][C:9]([C:5]2[N:4]=[C:3]([C:22]#[N:23])[C:2]3[N:1]=[CH:24][NH:8][C:7]=3[CH:6]=2)=[CH:10][C:11]=1[C:18]([F:21])([F:19])[F:20])[CH3:17]

Participants

5

Reactant 2

HCID 31214Ethyl orthoformateHCID 589381183,4-Diamino-6-(4-ethoxy-3-trifluoromethyl-phenyl)-pyridine-2-carbonitrile

Product 1

HCID 166621426-(4-Ethoxy-3-(trifluoromethyl)phenyl)-3H-imidazo[4,5-c]pyridine-4-carbonitrileYield 57.1%

Reagents, catalysts & solvents 2

HCID 2733225Ytterbium triflateCatalystHCID 6342AcetonitrileSolvent

Procedure

A stirred suspension of 3,4-diamino-6-(4-ethoxy-3-trifluoromethyl-phenyl)-pyridine-2-carbonitrile (4.4 g, 13.7 mmol), ytterbium triflate (173 mg, 2 mol %), triethylorthoformate (6.08 g, 41.1 mmol) and acetonitrile (50 ml) was heated to reflux for 30 minutes. The solid precipitate was collected by filtration and washed sparingly with acetonitrile to afford 6-(4-ethoxy-3-trifluoromethyl-phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile (2.6 g). 1H NMR (DMSO): δ 8.67 (s, 1H), 8.47 (s, 1H), 8.36 (m, 2H), 7,49 (d, 1H), 4.26 (q, 2H), 1.38 (t, 3H). MS m/z 333.3(M+1).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 30 minutes
  3. filtrationThe solid precipitate was collected by filtration
  4. washwashed sparingly with acetonitrile

Sources & evidence

ORD record
ord-90f233b348f24c53aa2c77f75ab22fcd
Source dataset
uspto-grants-2010_03
Patent number
US07687515B2

Reaction notes

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