Hydrazine → (+/-)-1-(6-Bromopyridin-2-yl)-2-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)ethanamine
Reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH:8]([N:28]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:9][C:10]2[CH:18]=[C:17]([CH3:19])[C:16]3[C:12](=[CH:13][N:14]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[N:15]=3)[CH:11]=2)[CH:5]=[CH:4][CH:3]=1.NN>CO>[Br:1][C:2]1[N:7]=[C:6]([CH:8]([NH2:28])[CH2:9][C:10]2[CH:18]=[C:17]([CH3:19])[C:16]3[C:12](=[CH:13][N:14]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:25])([CH3:27])[CH3:26])[N:15]=3)[CH:11]=2)[CH:5]=[CH:4][CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of (±)-2-(1-(6-bromopyridin-2-yl)-2-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)ethyl)isoindoline-1,3-dione (1 mmol) in methanol (10 mL) was treated with hydrazine (0.16 mL, 5 mmol) at room temperature for 30 min and at 70° C. for 5 h. The mixture was concentrated in vacuo and the residue was partitioned between 1N sodium hydroxide and ethyl acetate. The organic layer was washed with water, brine, dried and concentrated. The pale yellow oil (100%) was pure enough to carry on. MS (ESI) [M+H]+=461. HPLC tR=1.62 min.