Chloroacetaldehyde → 8-(Benzyloxy)-5-bromoimidazo[1,2-a]pyridine

HRID 1945604Notes

Reaction equation

HRID 1945604 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([NH2:16])=[N:11][C:12]([Br:15])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:18][CH:19]=O>>[CH2:1]([O:8][C:9]1[C:10]2[N:11]([CH:18]=[CH:19][N:16]=2)[C:12]([Br:15])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 33ChloroacetaldehydeHCID 596055123-(Benzyloxy)-6-bromopyridin-2-amine

Product 1

HCID 596052618-(Benzyloxy)-5-bromoimidazo[1,2-a]pyridineYield 88%

Procedure

A mixture of 3-benzyloxy-6-bromopyridin-2-ylamine (1.0 g, 3.6 mmol) and chloroacetaldehyde (1.2 mL, 50 wt. % in water) in IMS (12 mL) was stirred at reflux for 1 hour, then concentrated under reduced pressure. The residue was partitioned between an aqueous saturated solution of sodium bicarbonate and EtOAc. The organic layer was separated and washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography (Si—PPC, MeOH:Et2O, gradient 0:100 to 1:99) to give 8-Benzyloxy-5-bromo-imidazo[1,2-a]pyridine as an beige solid (960 mg, 88%). LCMS (Method H) RT 3.08 min; [M+H]+ 303 (79Br) and 305 (81Br)

Workup

  1. temperatureat reflux for 1 hour
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was partitioned between an aqueous saturated solution of sodium bicarbonate and EtOAc
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography (Si—PPC, MeOH:Et2O, gradient 0:100 to 1:99)

Sources & evidence

ORD record
ord-e439b2e1677841ddb63b3c820eeadb2c
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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