Bromotrimethylsilane → HCID 15888008, compound

HRID 1005472Notes

Reaction equation

HRID 1005472 reaction equation
C([O:3][P:4]([CH2:9][NH:10][C:11]([C:13]1[NH:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[CH:17][C:16]=2[N+:22]([O-:24])=[O:23])=[O:12])([O:6]CC)=[O:5])C.Br[Si](C)(C)C>C(#N)C>[P:4]([CH2:9][NH:10][C:11]([C:13]1[NH:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[CH:17][C:16]=2[N+:22]([O-:24])=[O:23])=[O:12])([OH:5])([OH:6])=[O:3]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 15888007HCID 15888007, compound

Product 1

HCID 15888008HCID 15888008, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 0.53 g (1.49 mmol) 2-(diethylphosphonomethylaminocarbonyl)-7-nitroindole in 7 mL acetonitrile was added 2 mL of bromotrimethylsilane at 0° C. The reaction mixture was allowed to stir at room temperature overnight. The solvent and excess bromotrimethylsilane were removed under reduced pressure and 10 mL of a 1/1 mixture of acetone/water was added and stirred for 24 hours at room temperature. A precipitate formed and the solid was filtered and dried to give 0.45 g (1.47 mmol, 99%) of 2-(phosphonomethylaminocarbonyl)-7-nitroindole.

Workup

  1. customThe solvent and excess bromotrimethylsilane were removed under reduced pressure and 10 mL of a 1/1 mixture of acetone/water
  2. additionwas added
  3. stirringstirred for 24 hours at room temperature
  4. customA precipitate formed
  5. filtrationthe solid was filtered
  6. customdried

Sources & evidence

ORD record
ord-74ab01cb9c624fd580169f49a3564cdc
Source dataset
uspto-grants-2000_04
Patent number
US06054587

Reaction notes

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