Triphenylphosphine → [4-cyano-6-(4-ethoxy-3-trifluoromethyl-phenyl)-1H-imidazo[4,5-c]pyridin-2-ylmethyl]-triphenyl-phosphonium chloride

HRID 2246449Notes

Reaction equation

HRID 2246449 reaction equation
[Cl:1][CH2:2][C:3]1[NH:4][C:5]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH3:19])=[C:13]([C:20]([F:23])([F:22])[F:21])[CH:12]=3)[N:8]=[C:7]([C:24]#[N:25])[C:6]=2[N:26]=1.[C:27]1([P:33]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(#N)C>[Cl-:1].[C:24]([C:7]1[C:6]2[N:26]=[C:3]([CH2:2][P+:33]([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[NH:4][C:5]=2[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH3:19])=[C:13]([C:20]([F:23])([F:22])[F:21])[CH:12]=2)[N:8]=1)#[N:25]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 589381142-chloromethyl-6-(4-ethoxy-3-trifluoromethyl-phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile

Product 1

HCID 86613868[4-cyano-6-(4-ethoxy-3-trifluoromethyl-phenyl)-1H-imidazo[4,5-c]pyridin-2-ylmethyl]-triphenyl-phosphonium chloride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Chloromethyl-6-(4-ethoxy-3-trifluoromethyl-phenyl)-1H-imidazo[4,5,c]-pyridine-4-carbonitrile (100 mg, 0.26 mmol) and triphenylphosphine in acetonitrile were heated to 60° C. and stirred overnight. The reaction mixture was concentrated and triturated with ether to give a light yellow solid. MS m/z 607.5 (m).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customtriturated with ether
  3. customto give a light yellow solid

Sources & evidence

ORD record
ord-530339d8bb8447a2a8bb3edc4fa03adb
Source dataset
uspto-grants-2010_03
Patent number
US07687515B2

Reaction notes

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