triethylorthoformate Acetic anhydride → 6-Bromo-4-chloro-3-methyl-imidazo[4,5-c]pyridine
Reaction equation
[Br:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([NH:9][CH3:10])=[C:4]([NH2:11])[CH:3]=1.[CH2:12](OC(OCC)OCC)C.C(OC(=O)C)(=O)C>>[Br:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]2[N:9]([CH3:12])[CH:10]=[N:11][C:4]=2[CH:3]=1Participants
3
Conditions
- Temperature
- 155 °C
Procedure
The above crude diamine 2.59-A was dissolved in a mixture of triethylorthoformate:Acetic anhydride (1:1, 9 mL). The reaction mixture was heated to 155° C. for 1 h, cooled to rt and then evaporated. The residue was dissolved in 2.5M NaOH (20 mL) and heated at 50° C. 45 min. The resulting solution was cooled to rt, neutralized with AcOH, and cooled to 0° C. The precipitate was filtered to give 6-bromo-4-chloro-3-methyl-3H-imidazo[4,5-c]pyridine 2.60.
Workup
- temperaturecooled to rt
- customevaporated
- dissolutionThe residue was dissolved in 2.5M NaOH (20 mL)
- temperatureheated at 50° C
- custom45 min
- temperatureThe resulting solution was cooled to rt
- temperaturecooled to 0° C
- filtrationThe precipitate was filtered
Sources & evidence
- ORD record
- ord-3460ffc78e9541578b29b5d1822a96a1
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09376441B2
Reaction notes
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