Ethyl bromopyruvate → Ethyl 7-methoxyimidazo[1,2-a]pyridine-2-carboxylate

HRID 530940Notes

Reaction equation

HRID 530940 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][N:3]=1.Br[CH2:11][C:12](=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14]>C(O)C>[CH3:9][O:8][C:6]1[CH:5]=[CH:4][N:3]2[CH:11]=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:1]=[C:2]2[CH:7]=1

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 108987152-Amino-4-Methoxypyridine

Product 1

HCID 20072865Ethyl 7-methoxyimidazo[1,2-a]pyridine-2-carboxylateYield 58.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-amino-4-methoxypyridine (1.0 g, 8.1 mmol) and ethyl 3-bromo-2-oxopropanoate (1.77 g, 9.1 mmol) in ethanol (10 mL) was refluxed for 6 h. After the reaction was concentrated, ethyl acetate (20 mL) was added to the residue. The mixture was basified by saturated aqueous sodium bicarbonate. The separated organic layer was washed with brine and dried over sodium sulfate. The solvent was evaporated and the residue obtained was purified by flash chromatography (silica gel, methylene chloride/ethyl acetate=1/1) to afford ethyl 7-methoxyimidazo[1,2-a]pyridine-2-carboxylate as a solid (1.04 g, 58%). 1H-NMR (DMSO-d6, 300 MHz): δ 8.37 (m, 2H), 6.91 (s, 1H), 6.70 (m, 1H), 4.25 (m, 2H), 3.81 (s, 3H), 1.28 (m, 3H) ppm; MS (ESI): 221.1 (M+1).

Workup

  1. temperaturewas refluxed for 6 h
  2. concentrationAfter the reaction was concentrated
  3. additionethyl acetate (20 mL) was added to the residue
  4. washThe separated organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was evaporated
  7. customthe residue obtained
  8. customwas purified by flash chromatography (silica gel, methylene chloride/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-80fdea686eab46a2b78892f5b1494397
Source dataset
uspto-grants-2016_05
Patent number
US09353111B2

Reaction notes

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