Bromotrimethylsilane → HCID 22179272, compound

HRID 854412Notes

Reaction equation

HRID 854412 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-4c140be5f70a4df1842a14d7b2c28ab0
Source dataset
uspto-grants-2007_08
Patent number
US07259172B2

Reaction notes

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