Chloroacetaldehyde → HCID 11160141, compound

HRID 1945597Notes

Reaction equation

HRID 1945597 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[C:4]([CH3:9])[CH:3]=1.Cl[CH2:11][CH:12]=O>>[Br:1][C:2]1[N:7]2[CH:11]=[CH:12][N:8]=[C:6]2[CH:5]=[C:4]([CH3:9])[CH:3]=1

Participants

3

Reactant 2

HCID 33ChloroacetaldehydeHCID 221765076-Bromo-4-methylpyridin-2-amine

Product 1

HCID 11160141HCID 11160141, compoundYield 82%

Conditions

Temperature
100 °C

Procedure

A mixture of 6-bromo-4-methyl-pyridin-2-ylamine (374 mg, 2.0 mmol) and chloroacetaldehyde (1 mL, 50 wt. % in water) in IMS (4 mL) was stirred at 100° C. in a sealed tube for 18 hours, then cooled to room temperature and loaded onto an Isolute® SCX-2 cartridge (10 g). The cartridge was washed with MeOH then the product was eluted with 2 M NH3 in MeOH. After the solvents were removed, the residue was purified by flash chromatography (Si—PPC, MeOH:DCM, gradient 0:100 to 5:95) to give 5-Bromo-7-methyl-imidazo[1,2-a]pyridine as an orange solid (340 mg, 82%). 1H NMR (400 MHz, CHCl3-d): δ 7.72-7.70 (m, 1 H); 7.63-7.62 (m, 1 H); 7.38-7.37 (m, 1 H); 6.92-6.90 (m, 1 H); 2.40 (m, 3 H).

Workup

  1. temperaturecooled to room temperature
  2. washThe cartridge was washed with MeOH
  3. washthe product was eluted with 2 M NH3 in MeOH
  4. customAfter the solvents were removed
  5. customthe residue was purified by flash chromatography (Si—PPC, MeOH:DCM, gradient 0:100 to 5:95)

Sources & evidence

ORD record
ord-2a09f4c8d3d14f868ab81b8981aa6321
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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