Bromotrimethylsilane → HCID 69507868, compound

HRID 851879Notes

Reaction equation

HRID 851879 reaction equation
[O:1]=[S:2]1(=[O:30])[C:7]2[CH:8]=[C:9]([O:12][C:13]3[CH:14]=[C:15]([P:19](=[O:26])([O:23]CC)[O:20]CC)[CH:16]=[CH:17][CH:18]=3)[CH:10]=[CH:11][C:6]=2[N:5]2[CH2:27][CH2:28][CH2:29][CH:4]2[NH:3]1.Br[Si](C)(C)C>C(#N)C>[O:30]=[S:2]1(=[O:1])[C:7]2[CH:8]=[C:9]([O:12][C:13]3[CH:14]=[C:15]([P:19](=[O:20])([OH:26])[OH:23])[CH:16]=[CH:17][CH:18]=3)[CH:10]=[CH:11][C:6]=2[N:5]2[CH2:27][CH2:28][CH2:29][CH:4]2[NH:3]1

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 86760522Diethyl 3-[(5,5-dioxido-2,3,3a,4-tetrahydro-1H-pyrrolo[2,1-c][1,2,4]benzothiadiazin-7-yl)oxy]phenylphosphonate

Product 1

HCID 69507868HCID 69507868, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Acetonitrile (20 ml), 0.66 mmol of the product of Example 52 and 1.98 mmol of bromotrimethylsilane are stirred at reflux for 1 h. The solvent and the excess of reagent are evaporated off in vacuo and the residue is taken up in solution in 10 ml of methanol. After stirring for 30 min., the solution is evaporated to dryness and the residue is taken up in 1N HCl. A gum is obtained which is crystallised by adding a small amount of CH2Cl2. The expected product is recovered by filtration.

Workup

  1. temperatureat reflux for 1 h
  2. customThe solvent and the excess of reagent are evaporated off in vacuo
  3. customthe solution is evaporated to dryness
  4. customA gum is obtained which
  5. customis crystallised
  6. additionby adding a small amount of CH2Cl2
  7. filtrationThe expected product is recovered by filtration

Sources & evidence

ORD record
ord-bcb894d185174890a1c95a0a2cc8ef25
Source dataset
uspto-grants-2007_08
Patent number
US07253161B2

Reaction notes

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