Azidotrimethylsilane → HCID 178433256, compound

HRID 1859072Notes

Reaction equation

HRID 1859072 reaction equation
F[C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]2[C:3]=1/[C:4](=[CH:15]/[C:16]1[NH:20][CH:19]=[N:18][C:17]=1[CH3:21])/[C:5](=[O:14])[NH:6]2.CCN(C(C)C)C(C)C.C[Si]([N:35]=[N+:36]=[N-:37])(C)C>C1COCC1.CCO>[N:35]([C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]2[C:3]=1/[C:4](=[CH:15]/[C:16]1[NH:20][CH:19]=[N:18][C:17]=1[CH3:21])/[C:5](=[O:14])[NH:6]2)=[N+:36]=[N-:37]

Participants

5

Reactant 3

HCID 78378AzidotrimethylsilaneHCID 81531DiisopropylethylamineHCID 178433250HCID 178433250, compound

Product 1

HCID 178433256HCID 178433256, compound

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

(Z)-1,3-Dihydro-4-fluoro-3-[(4-methyl-1H-imidazol-5-yl)methylene]-5-nitro-2H-indol-2-one (576 mg, 2.0 mmol) (from Example 42 above) was suspended in THF/EtOH (15 mL/8 mL). Hunig's base (diisopropylethyl amine, 5 mL, 30 mmol) (Aldrich) and trimethylsilyl azide (2.6 mL, 20 mmol) (Aldrich) were successively added at r.t. The mixture was heated at reflux for 3 h 20 min. The heterogeneous reaction mixture was cooled to r.t. and the orange suspension was collected by suction filtration. The precipitate was washed with ethanol and dried in a vacuum oven overnight. (Yield 490 mg, 79%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 h 20 min
  3. filtrationthe orange suspension was collected by suction filtration
  4. washThe precipitate was washed with ethanol
  5. customdried in a vacuum oven overnight

Sources & evidence

ORD record
ord-46e86dc4009f49d8bb16ccbbf89b332d
Source dataset
uspto-grants-2000_11
Patent number
US06153634

Reaction notes

Loading…