HCID 22100389, compound → HCID 22100372, compound

HRID 1457784Notes

Reaction equation

HRID 1457784 reaction equation
Br[C:2]1[CH:3]=[C:4]2[NH:12][C:11]([CH2:13][CH2:14][CH2:15][CH3:16])=[N:10][C:5]2=[N:6][C:7]=1[CH2:8][OH:9].[H][H]>C(O)C.[Pd]>[CH2:13]([C:11]1[NH:12][C:4]2[C:5]([N:10]=1)=[N:6][C:7]([CH2:8][OH:9])=[CH:2][CH:3]=2)[CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 2

HCID 22100389HCID 22100389, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22100372HCID 22100372, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

0.25 g(0.00088 mole) of 6-bromo-2-butyl-5-hydroxymethyl-1H-imidazo[4,5-b]pyridine obtained in step 6 of Example 1 was dissolved in 10 ml of ethanol and to the resulting solution was added 0.03 g of 10% palladium/activated carbon. The resultant was reacted at room temperature for 3 hours under about 3 atm of hydrogen using a hydrogenation apparatus. The reaction solution was filtered through Cellite with washing with 10% methanol/ethyl acetate(10 ml×3) and concentrated under reduced pressure to obtain 0.167 g of the title compound(yield 93%).

Workup

  1. filtrationThe reaction solution was filtered through Cellite
  2. washwith washing with 10% methanol/ethyl acetate(10 ml×3)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b18965a335d74663b28513932d8cb222
Source dataset
uspto-grants-1998_12
Patent number
US05849753

Reaction notes

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