Chloroacetaldehyde → 8-Bromo-6-chloroimidazo(1,2-a)pyridine
Reaction equation
[Br:1][C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.Cl[CH2:11][CH:12]=O>C(O)C>[Cl:8][C:6]1[CH:7]=[C:2]([Br:1])[C:3]2[N:4]([CH:11]=[CH:12][N:9]=2)[CH:5]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
A mixture of 3-bromo-5-chloropyridin-2-amine (10 g, 49 mmol) and chloroacetaldehyde (50% in H2O, 12 mL, 98 mmol) in ethanol (100 mL) was heated at 50° C. overnight. It was then cooled to room temperature and concentrated. Acetone (30 mL) was added to the residue and the resulting mixture was stirred rapidly for 2 h. The resulting solid was collected through filtration and dried to afford 101a as a yellow solid (10.0 g, 89%). MS: [M+H]+ 231. 1H NMR (500 MHz, DMSO) δ 9.20 (s, 1H), 8.33 (s, 1H), 8.29 (s, 1H), 8.09 (s, 1H)
Workup
- temperatureIt was then cooled to room temperature
- concentrationconcentrated
- additionAcetone (30 mL) was added to the residue
- filtrationThe resulting solid was collected through filtration
- customdried
Sources & evidence
- ORD record
- ord-739c5b50b4784913b3bc992a1b7d1acf
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08722676B2
Reaction notes
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