Hydrazine → (+/-)-1-(6-Bromopyridin-2-yl)-2-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)ethanamine

HRID 2099765Notes

Reaction equation

HRID 2099765 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]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 57794614(+/-)-2-(1-(6-Bromopyridin-2-yl)-2-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)ethyl)isoindoline-1,3-dione

Product 1

HCID 57794604(+/-)-1-(6-Bromopyridin-2-yl)-2-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)ethanamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was partitioned between 1N sodium hydroxide and ethyl acetate
  3. washThe organic layer was washed with water, brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-69171ab194f24e08b136a96076abb391
Source dataset
uspto-grants-2009_08
Patent number
US07569578B2

Reaction notes

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