Thiophene-3-boronic acid → 5-Chloro-2-([(2-([3-(thiophene-3-yl)phenyl]amino)-2-oxoethoxy)acetyl]amino)benzoic acid
Reaction equation
[S:1]1[CH:5]=[CH:4][C:3](B(O)O)=[CH:2]1.Br[C:10]1[CH:11]=[C:12]([NH:16][C:17](=[O:34])[CH2:18][O:19][CH2:20][C:21]([NH:23][C:24]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:25]=2[C:26]([OH:28])=[O:27])=[O:22])[CH:13]=[CH:14][CH:15]=1>>[Cl:33][C:30]1[CH:31]=[CH:32][C:24]([NH:23][C:21](=[O:22])[CH2:20][O:19][CH2:18][C:17]([NH:16][C:12]2[CH:13]=[CH:14][CH:15]=[C:10]([C:3]3[CH:4]=[CH:5][S:1][CH:2]=3)[CH:11]=2)=[O:34])=[C:25]([CH:29]=1)[C:26]([OH:28])=[O:27]Participants
3
Procedure
Using the same method as in Example 19-(ii), 3-thiopheneboronic acid was reacted with the 2-[((2-[(3-bromophenyl)amino]-2-oxoethoxy)acetyl)amino]-5-chlorobenzoic acid.methyl ester obtained in Example 19-(i) to give 5-chloro-2-([(2-([3-(thiophene-3-yl)phenyl]amino)-2-oxoethoxy)acetyl]amino)benzoic acid.methyl ester (yield: 82%).
Sources & evidence
- ORD record
- ord-885cca98d0924e25a57807c907adeda6
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08415479B2
Reaction notes
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