5-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxylic acid → HCID 44181664, compound
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)[C:6]([C:19](O)=[O:20])=[CH:5]2.[NH2:22][C:23]1[CH:24]=[C:25]2[N:31]=[C:30]([CH3:32])[S:29][C:26]2=[N:27][CH:28]=1>>[CH3:32][C:30]1[S:29][C:26]2[C:25]([N:31]=1)=[CH:24][C:23]([NH:22][C:19]([C:6]1[N:7]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=3)[C:8]3[C:4]([CH:5]=1)=[CH:3][C:2]([F:1])=[CH:10][CH:9]=3)=[O:20])=[CH:28][N:27]=2Participants
Procedure
The process is performed according to a method similar to that of Example 1.2, starting with 0.5 g (1.74 mmol) of 5-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxylic acid prepared in step 1.1 and 0.345 g (2.09 mmol) of 6-amino-2-methylthiazolo[5,4-b]pyridine (Yakugaku Zasshi 1950, 70, 187). At the end of the reaction, the product is concentrated under reduced pressure and then taken up in 100 mL of water. A precipitate is collected by filtration, and is purified by chromatography on a column of alumina, eluting with a mixture of dichloromethane and methanol. The resulting product is recrystallized from methanol, and a solid is collected by filtration, and dried under reduced pressure. 340 mg of the expected product are thus isolated.
Workup
- customAt the end of the reaction
- concentrationthe product is concentrated under reduced pressure
- filtrationA precipitate is collected by filtration
- customis purified by chromatography on a column of alumina
- washeluting with a mixture of dichloromethane and methanol
- customThe resulting product is recrystallized from methanol
- filtrationa solid is collected by filtration
- customdried under reduced pressure
Sources & evidence
- ORD record
- ord-cf296b84c2d449e794189a8cd0c4e7e6
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08604050B2
Reaction notes
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