Chloroacetaldehyde → 2-(3-Chloro-propenyl)-6-(4-ethoxy-3-trifluoromethyl-phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile

HRID 2246450Notes

Reaction equation

HRID 2246450 reaction equation
[Cl-].[C:2]([C:4]1[C:9]2[N:10]=[C:11]([CH2:13][P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[NH:12][C:8]=2[CH:7]=[C:6]([C:33]2[CH:38]=[CH:37][C:36]([O:39][CH2:40][CH3:41])=[C:35]([C:42]([F:45])([F:44])[F:43])[CH:34]=2)[N:5]=1)#[N:3].[Cl:46][CH2:47][CH:48]=O.N12CCCN=C1CCCCC2.C(O)C>C1COCC1>[Cl:46][CH2:47][CH:48]=[CH:13][C:11]1[NH:12][C:8]2[CH:7]=[C:6]([C:33]3[CH:38]=[CH:37][C:36]([O:39][CH2:40][CH3:41])=[C:35]([C:42]([F:44])([F:45])[F:43])[CH:34]=3)[N:5]=[C:4]([C:2]#[N:3])[C:9]=2[N:10]=1

Participants

6

Reactant 4

HCID 33ChloroacetaldehydeHCID 702EthanolHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86613868[4-cyano-6-(4-ethoxy-3-trifluoromethyl-phenyl)-1H-imidazo[4,5-c]pyridin-2-ylmethyl]-triphenyl-phosphonium chloride

Product 1

HCID 685177252-(3-Chloro-propenyl)-6-(4-ethoxy-3-trifluoromethyl-phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of [4-cyano-6-(4-ethoxy-3-trifluoromethyl-phenyl)-1H-imidazo[4,5-c]pyridin-2-ylmethyl]-triphenyl-phosphonium chloride (167.2 mg, 0.26 mmol), chloroacetaldehyde (50% in water) (32,6 mg, 0.41 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (62.4 mg, 0.41 mmol) was dissolved in a 1:1 mixture of THF:ethanol (4 ml) at room temperature overnight. The mixture was concentrated and purified on preparative HPLC to afford the title compound. MS m/z 407.5 (m+1).

Workup

  1. customat room temperature
  2. customovernight
  3. concentrationThe mixture was concentrated
  4. custompurified on preparative HPLC

Sources & evidence

ORD record
ord-094a89ad82b9434b91a59d1263b1b3c2
Source dataset
uspto-grants-2010_03
Patent number
US07687515B2

Reaction notes

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