Bromotrimethylsilane → 9-Trifluoromethyl-2,3-dioxo-1,2,3,5,6,7-hexahydro-pyrido[1,2,3-de]quinoxaline-5-phosphonic acid

HRID 1289427Notes

Reaction equation

HRID 1289427 reaction equation
C([O:3][P:4]([CH:9]1[N:14]2[C:15](=[O:27])[C:16](=[O:26])[NH:17][C:18]3[CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=[C:12]([C:13]=32)[CH2:11][CH2:10]1)(=[O:8])[O:5]CC)C.C[Si](Br)(C)C>C(#N)C>[F:24][C:22]([F:23])([F:25])[C:20]1[CH:21]=[C:12]2[CH2:11][CH2:10][CH:9]([P:4]([OH:8])(=[O:3])[OH:5])[N:14]3[C:15](=[O:27])[C:16](=[O:26])[NH:17][C:18]([CH:19]=1)=[C:13]23

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 15225059HCID 15225059, compound

Product 1

HCID 152250619-Trifluoromethyl-2,3-dioxo-1,2,3,5,6,7-hexahydro-pyrido[1,2,3-de]quinoxaline-5-phosphonic acidYield 79.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.63 g of 9-trifluoromethyl-2,3-dioxo-1,2,3,5,6,7-hexahydro-pyrido[1,2,3-de]quinoxaline-5-phosphonic acid diethyl ester is introduced into 40 ml of acetonitrile under nitrogen at room temperature. 3.63 ml of trimethylsilylbromide is rapidly instilled. The solution is stirred for 20 hours at room temperature and concentrated by evaporation. The residue is suspended in 50 ml of water, suctioned off and washed with water. The residue is dried at 105° C. and 0.7 torr. 1.12 g of 9-trifluoromethyl-2,3-dioxo-1,2,3,5,6,7-hexahydro-pyrido[1,2,3-de]quinoxaline-5-phosphonic acid of melting point 262° C. is obtained.

Workup

  1. concentrationconcentrated by evaporation
  2. washwashed with water
  3. customThe residue is dried at 105° C.

Sources & evidence

ORD record
ord-5cfccadf6c114d06a3915ee14a626307
Source dataset
uspto-grants-1998_05
Patent number
US05750526

Reaction notes

Loading…