Chloroacetaldehyde → HCID 68775112, compound

HRID 1711180Notes

Reaction equation

HRID 1711180 reaction equation
[Br:1][C:2]1[C:3]([CH3:10])=[CH:4][C:5]([NH2:9])=[N:6][C:7]=1[CH3:8].Cl[CH2:12][CH:13]=O.C1(C)C=CC=CC=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:1][C:2]1[C:3]([CH3:10])=[CH:4][C:5]2[N:6]([CH:12]=[CH:13][N:9]=2)[C:7]=1[CH3:8]

Participants

6

Reactant 4

HCID 33ChloroacetaldehydeHCID 1140TolueneHCID 516892Sodium BicarbonateHCID 110308555-Bromo-4,6-dimethylpyridin-2-amine

Product 1

HCID 68775112HCID 68775112, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Bromo-4,6-dimethyl-pyridin-2-ylamine (1.51 g, 7.5 mmol) and chloroacetaldehyde (0.95 ml, 50% in water, 7.5 mmol) were mixed with toluene (12 ml). The mixture was heated to reflux for 3 h, upon which time a dark solid residue appeared at the bottom of the reaction flask. After cooling down to rt, NaHCO3 (20 ml, sat. aq.) and CH2Cl2 (20 ml) were added. Layers were separated and the aqueous layer was further extracted with CH2Cl2 (20 ml×2). The combined CH2Cl2 was dried (Na2SO4), filtered and concentrated. The residue was purified by column chromatography on silica gel (CH2Cl2/CH3OH, 18:1) to give the 6-bromo-5,7-dimethyl-imidazo[1,2-a]pyridine as a yellow oil (985 mg, 58%, contaminated with some starting material).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 h, upon which time a dark solid residue
  3. customLayers were separated
  4. extractionthe aqueous layer was further extracted with CH2Cl2 (20 ml×2)
  5. dry with materialThe combined CH2Cl2 was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography on silica gel (CH2Cl2/CH3OH, 18:1)

Sources & evidence

ORD record
ord-fb721282c28e46e88e480d41ad2c73c4
Source dataset
uspto-grants-2010_09
Patent number
US07790747B2

Reaction notes

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