2-methylimidazo[1,2-a]pyridine-3-carbaldehyde → (2-methylimidazo[1,2-a]pyridin-3-yl)methanol

HRID 630169Notes

Reaction equation

HRID 630169 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1[N:5]=[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][N:7]2[C:12]=1[CH:13]=[O:14]>CO>[CH3:3][C:4]1[N:5]=[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][N:7]2[C:12]=1[CH2:13][OH:14]

Participants

4

Reactant 2

HCID 27598592-methylimidazo[1,2-a]pyridine-3-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 7060539(2-methylimidazo[1,2-a]pyridin-3-yl)methanolYield 59%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of sodium borohydride (531 mg, 14.0 mmol) in methanol (30 mL) was added a solution of 2-methylimidazo[1,2-a]pyridine-3-carbaldehyde (1.5 g, 9.4 mmol) in methanol (5 mL) at 0° C. The mixture was stirred for 2 hours at room temperature. The solvent was evaporated, water was added, and the mixture was extracted 3 times with ethyl acetate. The organic phase was washed with brine and dried over sodium sulfate. After evaporation of the solvent, {2-methylimidazo[1,2-a]pyridin-3-yl}methanol was obtained (914 mg, 59% yield) and used in the next step without further purification; 1H NMR (400 MHz, DMSO-d6): δ 2.31 (s, 3H), 4.74 (d, J=5.4 Hz, 2H), 5.06 (t, J=5.4 Hz, 1H), 6.86 (dt, J=6.8 Hz, J=1.3 Hz, 1H), 7.16-7.21 (m, 1H), 7.42 (td, J=9.0 Hz, J=1.2 Hz, 1H), 8.28 (td, J=6.8 Hz, J=1.2 Hz, 1H).

Workup

  1. customThe solvent was evaporated
  2. additionwater was added
  3. extractionthe mixture was extracted 3 times with ethyl acetate
  4. washThe organic phase was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-34962909ff524d07ad1bd1e563a3e00c
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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