Chloromalonaldehyde → 7-(4-Bromo-2-chlorophenylamino)-8-chloro-3-formyl-imidazo[1,2-a]pyridine-6-carboxylic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[C:9]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][C:12]=2[Cl:18])=[C:8]([Cl:19])[C:7]([NH2:20])=[N:6][CH:5]=1.Cl[CH:23]([CH:26]=O)[CH:24]=[O:25]>>[CH3:1][O:2][C:3]([C:4]1[C:9]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][C:12]=2[Cl:18])=[C:8]([Cl:19])[C:7]2[N:6]([C:23]([CH:24]=[O:25])=[CH:26][N:20]=2)[CH:5]=1)=[O:21]Participants
3
Conditions
- Temperature
- 80 °C
Procedure
A suspension of 6-amino-4-(4-bromo-2-chlorophenylamino)-5-chloro-nicotinic acid methyl ester (28) (1.06 g, 2.72 mmol) and 2-chloro-malonaldehyde (587 mg, 5.43 mmol) was heated to 80° C. for 45 minutes. The solution was allowed to cool to room temperature, and then washed with saturated aqueous NaHCO3, and brine. The organic layer was dried over NaSO4, filtered, concentrated in vacuo, and purified by column chromatography (20:1 methylene chloride/methanol) to give the desired product as a dark yellow solid. The solid was triturated with ethyl acetate and isolated by filtration to provide the desired product as a yellow solid (0.436 g, 36%). MS (APCI+) m/z 442, 444, 446 (M+; Cl, Br pattern) detected.
Workup
- temperatureto cool to room temperature
- washwashed with saturated aqueous NaHCO3, and brine
- dry with materialThe organic layer was dried over NaSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- custompurified by column chromatography (20:1 methylene chloride/methanol)
Sources & evidence
- ORD record
- ord-55d0c8997ce94a4e99229f4c63e6fc73
- Source dataset
- uspto-grants-2007_09
- Patent number
- US07271178B2
Reaction notes
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