Sodium Hydroxide → Imidazo[1,2-a]pyridine-7-methanol

HRID 408570Notes

Reaction equation

HRID 408570 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][N:8]2[CH:11]=[CH:12][N:13]=[C:7]2[CH:6]=1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C1COCC1>[N:13]1[CH:12]=[CH:11][N:8]2[CH:9]=[CH:10][C:5]([CH2:3][OH:2])=[CH:6][C:7]=12

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 15096964Methyl imidazo(1,2-a)pyridine-7-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 11051824Imidazo[1,2-a]pyridine-7-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a −78° C. cooled solution of imidazo[1,2-a]pyridine-7-carboxylic acid methyl ester (1 eq.) in dry THF was slowly added a solution of LiAlH4 in THF (1M in THF, 2 eq.). The reaction mixture was warmed to 0° C. and stirred for 30 min. The reaction mixture was then poured onto a cooled aqueous solution of NaOH 2N, stirred for 5 min and filtered through a pad of celite. The filtrate was partitioned between water and EtOAc, the organic layer was washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure to afford imidazo[1,2-a]pyridin-7-yl-methanol which was used as such without further purification.

Workup

  1. stirringstirred for 5 min
  2. filtrationfiltered through a pad of celite
  3. customThe filtrate was partitioned between water and EtOAc
  4. washthe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fcf8591d91854d84b39396c492629ec7
Source dataset
uspto-grants-2014_06
Patent number
US08759334B2

Reaction notes

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