Trimethylsilyl iodide → HCID 11701500, compound

HRID 30254Notes

Reaction equation

HRID 30254 reaction equation
C(OC([N:6]1[CH2:17][CH:9]2[C:10]3[CH:11]=[C:12]([Br:16])[S:13][C:14]=3[CH2:15][CH:8]2[CH2:7]1)=O)C.I[Si](C)(C)C>C(Cl)Cl.CO>[Br:16][C:12]1[S:13][C:14]2[CH2:15][CH:8]3[CH2:7][NH:6][CH2:17][CH:9]3[C:10]=2[CH:11]=1

Participants

5

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 131727032HCID 131727032, compound

Product 1

HCID 11701500HCID 11701500, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

The product of step c) (20.9 mg, 0.07 mmol) in CH2Cl2 (330 μl) was treated with iodotrimethylsilane (19.8 mg, 0.099 mmol) at 50° C. for 16 hours. The solvent was evaporated in vacuo leaving a brown residue that was dissolved in MeOH and a portion purified by preparative LC/MS to give the title compound. 1H NMR (300 MHz, CDCl3, ppm) 2.76-2.81 (m, 1H); 2.95-3.03 (m, 1H); 3.12-3.22 (m, 2H); 3.44-3.61 (m, 3H); 3.81-3.85 (m, 1H); 6.78 (s, 1H); 9.20-9.4 (br s, 2H); MS calculated for C9H10BrNS+H 244, observed 244, 246.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customleaving a brown residue that
  3. customa portion purified by preparative LC/MS

Sources & evidence

ORD record
ord-11df1021907e43ef816ac0adefbbeae0
Source dataset
uspto-grants-2008_09
Patent number
US07423056B2

Reaction notes

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