1H-Indole-2,3-dione, 6-bromo- → 3-hydroxy-3-methyl-6-[8-(1-methyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-2-ylamino]-1,3-dihydro-indol-2-one
Reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[C:8]3[N:9]([N:13]=[C:14]([NH2:16])[N:15]=3)[CH:10]=[CH:11][N:12]=2)[CH:4]=[N:3]1.Br[C:18]1[CH:26]=[C:25]2[C:21]([C:22]([OH:29])([CH3:28])[C:23](=[O:27])[NH:24]2)=[CH:20][CH:19]=1.C[Mg]Br.BrC1C=C2C(C(=O)C(=O)N2)=CC=1>>[OH:29][C:22]1([CH3:28])[C:21]2[C:25](=[CH:26][C:18]([NH:16][C:14]3[N:15]=[C:8]4[C:7]([C:5]5[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=5)=[N:12][CH:11]=[CH:10][N:9]4[N:13]=3)=[CH:19][CH:20]=2)[NH:24][C:23]1=[O:27]Participants
5
Reactant 4
Product 1
Procedure
8-(1-Methylpyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-2-amine is reacted with 6-bromo-3-hydroxy-3-methyl-1,3-dihydro-indol-2-one, available via addition of methymagnesiumbromide to 6-bromo-Isatin, to give the title compound as a solid.
Sources & evidence
- ORD record
- ord-1cf3d0cc6dd14e56ae9cda8013078508
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09120804B2
Reaction notes
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