Iodine → HCID 58574195, compound

HRID 1619302Notes

Reaction equation

HRID 1619302 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:23](=[O:26])[NH:24][CH3:25])=[C:6]([NH:8][C:9]([CH:11]2[CH2:15][CH2:14][CH2:13][N:12]2C(OC(C)(C)C)=O)=O)[CH:7]=1.C[Si](C)(C)N[Si](C)(C)C.II.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]2[C:5]([C:23](=[O:26])[N:24]([CH3:25])[C:9]([CH:11]3[CH2:15][CH2:14][CH2:13][NH:12]3)=[N:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 807IodineHCID 13838HexamethyldisilazaneHCID 24477Sodium ThiosulfateHCID 69937721HCID 69937721, compound

Product 1

HCID 58574195HCID 58574195, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The mixture of tert-butyl 2-(5-bromo-2-(methylcarbamoyl)phenylcarbamoyl)pyrrolidine-1-carboxylate (0.2 g, 0.47 mmol), hexamethyldisilazane (0.39 mL, 1.88 mmol), I2 (0.24 g, 0.94 mmol), and DCM (10 mL) was refluxed for 5 h under nitrogen atmosphere. Na2S2O3 aqueous solution was added to quench the reaction followed by cooling to room temperature. The organic layer was separated and the water layer was extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and evaporated to give the desired product, which was directly used for the next step. MS (ESI): 308, 310 (MH+).

Workup

  1. temperaturewas refluxed for 5 h under nitrogen atmosphere
  2. customto quench the reaction
  3. customThe organic layer was separated
  4. extractionthe water layer was extracted with ethyl acetate (3×10 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-38bbbf828ad84c22a2a663bbb3a8cd91
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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