Potassium Hydroxide → HCID 178441502, compound

HRID 1586839Notes

Reaction equation

HRID 1586839 reaction equation
[CH2:1]([C:5]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:25]=[C:24](Cl)[S:23][C:22]=3[C:27]3[NH:31][N:30]=[N:29][N:28]=3)=[CH:17][CH:16]=2)[C:8]2=[N:9][CH:10]=[CH:11][CH:12]=[C:7]2[N:6]=1)[CH2:2][CH2:3][CH3:4].[OH-].[K+]>[Pd].CO>[CH2:1]([C:5]1[N:13]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]3[CH:25]=[CH:24][S:23][C:22]=3[C:27]3[NH:31][N:30]=[N:29][N:28]=3)=[CH:19][CH:20]=2)[C:8]2=[N:9][CH:10]=[CH:11][CH:12]=[C:7]2[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 178441501HCID 178441501, compound

Product 1

HCID 178441502HCID 178441502, compoundYield 91.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-butyl-3-[4-[5-chloro-2-(1H-tetrazol-5-yl)-3-thienyl]benzyl]-3H-imidazo[4,5-b]pyridine (330 mg), 10% palladium on carbon (103 mg), potassium hydroxide (261 mg) and methanol (15 ml) was stirred under hydrogen atmosphere (1 atm) at ambient temperature for 3 hours. The reaction mixture was filtered through cellulose powder and the filtrate was evaporated in vacuo. The residue was dissolved in water and neutralized with 1N hydrochloric acid. The precipitate was collected by vacuum filtration to afford a white powder of 2-butyl-3-[4-[2-(1H-tetrazol-5-yl)-3-thienyl]benzyl]-3H-imidazo[4,5-b]pyridine (279 mg).

Workup

  1. filtrationThe reaction mixture was filtered through cellulose powder
  2. customthe filtrate was evaporated in vacuo
  3. dissolutionThe residue was dissolved in water and neutralized with 1N hydrochloric acid
  4. filtrationThe precipitate was collected by vacuum filtration

Sources & evidence

ORD record
ord-ee22d58dbb2e48f0b49dc010e4af6e91
Source dataset
uspto-grants-1993_06
Patent number
US05215994

Reaction notes

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