Chloroacetone → 6-Bromo-2-methylimidazo[1,2-a]pyridine

HRID 626923Notes

Reaction equation

HRID 626923 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.Cl[CH2:10][C:11](=O)[CH3:12]>C(O)C>[Br:8][C:5]1[CH:6]=[CH:7][C:2]2[N:3]([CH:10]=[C:11]([CH3:12])[N:1]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 6571ChloroacetoneHCID 706222-Amino-5-bromopyridine

Product 1

HCID 124289606-Bromo-2-methylimidazo[1,2-a]pyridineYield 73.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

2-Amino-5-bromopyridine (10 g, 57.8 mmol) was dissolved in ethanol (100 mL) and chloroacetone (9.3 mL, 115.59 mmol) was added. The mixture was heated to reflux at 90° C. for 16 h. The reaction mixture was concentrated under vacuum and the residue was purified by flash chromatography, eluting with a gradient of 0-20% methanol in DCM, to afford the title compound (9 g, 66.4%) as a yellow solid. δH (500 MHz, CD3OD) 9.03 (s, 1H), 8.02 (m, 1H), 7.93 (s, 1H), 7.79 (d, J 9.4 Hz, 1H), 2.56 (s, 3H).

Workup

  1. temperatureThe mixture was heated
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. customthe residue was purified by flash chromatography
  4. washeluting with a gradient of 0-20% methanol in DCM

Sources & evidence

ORD record
ord-717429bc5d594dc3900556e2074b4b52
Source dataset
uspto-grants-2016_04
Patent number
US09309243B2

Reaction notes

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