1H-Indole-2,3-dione, 6-bromo- → HCID 89767111, compound

HRID 2273018Notes

Reaction equation

HRID 2273018 reaction equation
[CH:1]([Mg]Cl)([CH3:3])[CH3:2].[Br:6][C:7]1[CH:15]=[C:14]2[C:10]([C:11](=[O:17])[C:12](=[O:16])[NH:13]2)=[CH:9][CH:8]=1>C1COCC1>[Br:6][C:7]1[CH:15]=[C:14]2[C:10]([C:11]([OH:17])([CH:1]([CH3:3])[CH3:2])[C:12](=[O:16])[NH:13]2)=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 957161H-Indole-2,3-dione, 6-bromo-HCID 178418918HCID 178418918, compound

Product 1

HCID 89767111HCID 89767111, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Addition of isopropylmagnesiumchloride to 6-bromoisatin at −78° C. in THF gives after usual workup 6-bromo-3-hydroxy-3-isopropyl-1,3-dihydro-indol-2-one which is reacted with 8-(1-methyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-2-ylamine using general procedure 2 to give the title compound as a solid.

Sources & evidence

ORD record
ord-c795261a236340cf98ceb351a4df2966
Source dataset
uspto-grants-2015_09
Patent number
US09120804B2

Reaction notes

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