Sodium borohydride → HCID 11513907, compound

HRID 2055134Notes

Reaction equation

HRID 2055134 reaction equation
C([O:3][C:4](=O)[C:5]([N:8]1[C:16]2[C:11](=[N:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[CH:9]1)([CH3:7])[CH3:6])C.[BH4-].[Na+]>C(O)C>[N:8]1([C:5]([CH3:7])([CH3:6])[CH2:4][OH:3])[C:16]2[C:11](=[N:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[CH:9]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 11550420HCID 11550420, compound

Product 1

HCID 11513907HCID 11513907, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-imidazo[4,5-b]pyridin-1-yl-2-methyl-propionic acid ethyl ester (1 eq) in ethanol was added sodium borohydride (4 eq) at room temperature. The reaction mixture was left stirring at room temperature overnight and then quenched by addition of H2O. Once the reaction solvent was removed in vacuo, the residue was dissolved in dichloromethane, washed with NaCl (sat.), dried over sodium sulfate, filtered, and concentrated to give compound 2-imidazo[4,5-b]pyridin-1-yl-2-methyl-propan-1-ol (92%) MH+(192)

Workup

  1. waitThe reaction mixture was left
  2. customquenched by addition of H2O
  3. customOnce the reaction solvent was removed in vacuo
  4. dissolutionthe residue was dissolved in dichloromethane
  5. washwashed with NaCl (sat.)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f49deee7f86e46ceb4029a05880c538d
Source dataset
uspto-grants-2008_02
Patent number
US07332476B2

Reaction notes

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