Sodium hydride → 2-butyl-3-[4-[4-ethoxycarbonyl-2-(1-trityl-1H-tetrazol-5-yl)-1-pyrrolyl]benzyl]-7-methyl-3H-imidazo[4,5-b]pyridine

HRID 248412Notes

Reaction equation

HRID 248412 reaction equation
[H-].[Na+].[CH2:3]([C:7]1[NH:8][C:9]2[C:10]([N:16]=1)=[N:11][CH:12]=[CH:13][C:14]=2[CH3:15])[CH2:4][CH2:5][CH3:6].[CH2:17]([O:19][C:20]([C:22]1[CH:23]=[C:24]([C:39]2[N:43]([C:44]([C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[N:42]=[N:41][N:40]=2)[N:25]([C:27]2[CH:32]=[CH:31][C:30]([CH2:33]OS(C)(=O)=O)=[CH:29][CH:28]=2)[CH:26]=1)=[O:21])[CH3:18]>CS(C)=O.[Cl-].[Na+].O>[CH2:3]([C:7]1[N:16]([CH2:33][C:30]2[CH:29]=[CH:28][C:27]([N:25]3[CH:26]=[C:22]([C:20]([O:19][CH2:17][CH3:18])=[O:21])[CH:23]=[C:24]3[C:39]3[N:43]([C:44]([C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)([C:57]4[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=4)[C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=4)[N:42]=[N:41][N:40]=3)=[CH:32][CH:31]=2)[C:10]2=[N:11][CH:12]=[CH:13][C:14]([CH3:15])=[C:9]2[N:8]=1)[CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 150152652-Butyl-7-methyl-1H-imidazo[4,5-b]pyridineHCID 197593244-ethoxycarbonyl-1-(4-methanesulfonyloxymethylphenyl)-2-(1-trityl-1H-tetrazol-5-yl)pyrrole

Product 1

HCID 197592572-butyl-3-[4-[4-ethoxycarbonyl-2-(1-trityl-1H-tetrazol-5-yl)-1-pyrrolyl]benzyl]-7-methyl-3H-imidazo[4,5-b]pyridine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

Sodium hydride (10 mg) (60% in oil) was added to a stirred solution of 2-butyl-7-methylimidazo[4,5-b]pyridine mg) in dimethyl sulfoxide (5.0 ml) and the mixture was stirred for 30 minutes at ambient temperature. To this mixture was added a solution of 4-ethoxycarbonyl-1-(4-methanesulfonyloxymethylphenyl)-2-(1 -trityl-1H-tetrazol-5-yl)pyrrole (193 mg) in dimethyl sulfoxide (2 ml). The mixture was stirred for 3 hours at ambient temperature and poured into brine. The mixture was extracted with ethyl acetate, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin layer chromatography to afford 2-butyl-3-[4-[4-ethoxycarbonyl-2-(1-trityl-1H-tetrazol-5-yl)-1-pyrrolyl]benzyl]-7-methyl-3H-imidazo[4,5-b]pyridine (123 mg) as a colorless viscous oil.

Workup

  1. stirringThe mixture was stirred for 3 hours at ambient temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-65e6d1338e644f0da75a42eb55535eea
Source dataset
uspto-grants-1993_05
Patent number
US05210092

Reaction notes

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