1,3,5-Trimethylpyrazole-4-boronic acid → 3,3-dimethyl-6-[8-(1,3,5-trimethyl-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[C:6]([CH3:7])=[C:5]([C:8]2[C:9]3[N:10]([N:14]=[C:15]([NH2:17])[N:16]=3)[CH:11]=[CH:12][N:13]=2)[C:4]([CH3:18])=[N:3]1.ClC1C2N(N=C(N)N=2)C=CN=1.CN1C(C)=C(B(O)O)C(C)=N1.Cl[C:42]1[CH:50]=[C:49]2[C:45]([C:46]([CH3:53])([CH3:52])[C:47](=[O:51])[NH:48]2)=[CH:44][CH:43]=1>>[CH3:52][C:46]1([CH3:53])[C:45]2[C:49](=[CH:50][C:42]([NH:17][C:15]3[N:16]=[C:9]4[C:8]([C:5]5[C:4]([CH3:18])=[N:3][N:2]([CH3:1])[C:6]=5[CH3:7])=[N:13][CH:12]=[CH:11][N:10]4[N:14]=3)=[CH:43][CH:44]=2)[NH:48][C:47]1=[O:51]Participants
5
Reactant 4
Product 1
Procedure
8-(1,3,5-Trimethylpyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-2-amine, synthesized by reaction of 8-chloro-[1,2,4]triazolo[1,5-a]pyrazin-2-ylamine with (1,3,5-trimethylpyrazol-4-yl)boronic acid following procedure 1, is coupled with 6-chloro-3,3-dimethyl-1,3-dihydro-indol-2-one under Buchwald Hartwig conditions using general procedure 2.
Sources & evidence
- ORD record
- ord-ef91511b78254e97933eed1546f142fe
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09120804B2
Reaction notes
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