Ethyl imidazo[1,2-a]pyridine-2-carboxylate → Imidazo[1,2-a]pyridin-2-ylmethanol

HRID 577039Notes

Reaction equation

HRID 577039 reaction equation
[N:1]1[C:2]([C:10](OCC)=[O:11])=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C.ClCCl>[N:1]1[C:2]([CH2:10][OH:11])=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

5

Reactant 2

HCID 818807Ethyl imidazo[1,2-a]pyridine-2-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 2795540Imidazo[1,2-a]pyridin-2-ylmethanol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Ethyl imidazo[1,2-a]pyridine-2-carboxylate (1.5 g, 7.9 mmol) was dissolved in diethyl ether (30 mL) and dichloromethane (20 mL). Lithium aluminum hydride (450 mg, 11.8 mmol) was added at 0° C., and the mixture was stirred 3 hours at room temperature. The reaction was quenched with an aqueous solution of sodium hydroxide and extracted 5 times with ethyl acetate. The combined organic phase was washed with brine and dried over sodium sulfate. After evaporation of the solvent, imidazo[1,2-a]pyridin-2-ylmethanol was obtained as a yellow oil (527 mg, 45% yield) and used in the next step without purification; 1H NMR (400 MHz, CDCl3): δ 4.86 (s, 2H), 6.76-6.80 (m, 1H), 7.15-7.20 (m, 1H), 7.55-7.58 (m, 2H), 8.09 (d, J=6.8 Hz, 1H).

Workup

  1. customThe reaction was quenched with an aqueous solution of sodium hydroxide
  2. extractionextracted 5 times with ethyl acetate
  3. washThe combined organic phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-b19fd673d6a247638951e9d2133cf3ee
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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