Bromotrimethylsilane → HCID 22179272, compound

HRID 896991Notes

Reaction equation

HRID 896991 reaction equation
C[O:2][P:3]([CH2:7][N:8]([S:10]([C:13]1[S:14][C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[CH:17]=1)(=[O:12])=[O:11])[CH3:9])(=[O:6])[O:4]C.Br[Si](C)(C)C>ClCCl>[S:14]1[C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[CH:17]=[C:13]1[S:10]([N:8]([CH2:7][P:3](=[O:2])([OH:6])[OH:4])[CH3:9])(=[O:11])=[O:12]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 22890941HCID 22890941, compound

Product 1

HCID 22179272HCID 22179272, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 550 mg (1.58 mmol) of the compound (xiv) in 10 mL of anhydrous dichloromethane at 0° C., 0.49 mL of bromotrimethylsilane was added. The mixture was warmed up to room temperature and left overnight. Dichloromethane was evaporated; the oily residue was dissolved in another 10 mL of dichloromethane, filtered, again evaporated and redissolved in 10 mL of MeOH. The methanolic solution stirred at room temperature 30 min., evaporated and the residue was triturated with a mixture ether/hexane to form a white crystalline product which was separated by filtration (390 mg, 70%): 1H NMR: (300 MHz, DMSO-D6) δH 2.88 (s, CH3), 3.21 (d, J=12.1 Hz, 2H), 7.49-7.61 (m, 2H, Ar—H), 8.01-8.17 (m, 3H, Ar—H).

Workup

  1. customDichloromethane was evaporated
  2. dissolutionthe oily residue was dissolved in another 10 mL of dichloromethane
  3. filtrationfiltered
  4. customagain evaporated
  5. dissolutionredissolved in 10 mL of MeOH
  6. customevaporated
  7. customthe residue was triturated with a mixture ether/hexane
  8. customto form a white crystalline product which
  9. customwas separated by filtration (390 mg, 70%)

Sources & evidence

ORD record
ord-a1bfd22e7f7344d69b107a4f12bf4e10
Source dataset
uspto-grants-2005_07
Patent number
US06921756B2

Reaction notes

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