HCID 21071406, compound → HCID 21071593, compound

HRID 1666850Notes

Reaction equation

HRID 1666850 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([Si:14]([CH:21]([CH3:23])[CH3:22])([CH:18]([CH3:20])[CH3:19])[CH:15]([CH3:17])[CH3:16])[CH:9]=[C:8]2[CH2:24][CH2:25][N:26]1C(=O)C2C(=CC=CC=2)C1=O)[CH2:2][CH3:3]>CCO.O.NN>[CH2:1]([O:4][C:5]1[CH:6]=[C:7]2[C:11]([N:10]([Si:14]([CH:21]([CH3:22])[CH3:23])([CH:18]([CH3:20])[CH3:19])[CH:15]([CH3:16])[CH3:17])[CH:9]=[C:8]2[CH2:24][CH2:25][NH2:26])=[CH:12][CH:13]=1)[CH2:2][CH3:3]

Participants

4

Reactant 1

HCID 21071406HCID 21071406, compound

Product 1

HCID 21071593HCID 21071593, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 24654Hydrazine hydrate (1:1)Solvent

Procedure

Combine 2-(2-(5-propoxy-1-triisopropylsilanyl-1H-indol-3-yl)ethyl)isoindole-1,3-dione (416 mg, 0.8 mmol) in 20 mL EtOH and 1 mL hydrazine hydrate. Reflux for 3 hours, filter through celite and concentrate to residue. Dissolve the residue in 10 mL MeOH and load onto a 12 g SCX ion exchange cartridge and rinse sequentially with MeOH, DMF, then MeOH. Elute the product with 2 M NH3 in MeOH to give the title compound as an oil: ISMS 375 (M+1); 1H NMR (CDCl3) 7.34-7.32 (d, 1H), 7.02 (s, 1H), 7.00-6.99 (d, 1H), 6.80-6.77 (m, 1H), 3.97-3.94 (m, 2H), 3.01-2.98 (m, 2H), 2.86-2.83 (m, 2H), 1.88-1.76 (m, 2H), 1.70-1.58 (m, 3H), 1.3 (bs, 2H), 1.14-1.08 (m, 18H), 1.06-1.02 (t, 3H).

Workup

  1. temperatureReflux for 3 hours
  2. filtrationfilter through celite
  3. concentrationconcentrate to residue
  4. dissolutionDissolve the residue in 10 mL MeOH
  5. washload onto a 12 g SCX ion exchange cartridge and rinse sequentially with MeOH, DMF
  6. washElute the product with 2 M NH3 in MeOH

Sources & evidence

ORD record
ord-c3895d9a8209447993269ec944c95345
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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