Iodine → HCID 131731376, compound

HRID 1020881Notes

Reaction equation

HRID 1020881 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][C@H:8]1[CH2:13][CH2:12][C:11](=[O:14])[NH:10][C@@H:9]1[C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1[F:22])([CH3:4])([CH3:3])[CH3:2].CN(C)CCN(C)C.[I:32][Si](C)(C)C.II.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[C:1]([O:5][C:6](=[O:23])[NH:7][C@H:8]1[CH2:13][CH:12]([I:32])[C:11](=[O:14])[NH:10][C@@H:9]1[C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1[F:22])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 5

HCID 807IodineHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 24477Sodium ThiosulfateHCID 85247Trimethylsilyl iodideHCID 131731375HCID 131731375, compound

Product 1

HCID 131731376HCID 131731376, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the product from Step B (2 g, 6.13 mmol) in dichloromethane (50 mL) at 0° C. was added N,N,N′,N′-tetramethylethylenediamine (4.62 mL, 30.6 mmol) followed by slow addition of iodotrimethylsilane (2.59 mL, 19.0 mmol). The yellow mixture was stirred for 2 h at 0° C. and iodine (3.11 g, 12.26 mmol) was added in one portion. The mixture was stirred for 3 h at ° C. and saturated aqueous sodium thiosulfate (50 mL) added. The mixture was stirred for 10 min, the layers were separated and the aqueous phase extracted with dichloromethane (3×25 mL) and the combined organic phases dried with anhydrous sodium sulfate, filtered and the solvent removed in vacuo. The crude yellow solid was purified by column chromatography (silica gel Biotage 40S) eluting with ethyl acetate/hexane (gradient from 0% to 100%) to give the title compound as a colorless solid. LC/MS 453.2 (M+1).

Workup

  1. stirringThe mixture was stirred for 3 h at ° C
  2. stirringThe mixture was stirred for 10 min
  3. customthe layers were separated
  4. extractionthe aqueous phase extracted with dichloromethane (3×25 mL)
  5. dry with materialthe combined organic phases dried with anhydrous sodium sulfate
  6. filtrationfiltered
  7. customthe solvent removed in vacuo
  8. customThe crude yellow solid was purified by column chromatography (silica gel Biotage 40S)
  9. washeluting with ethyl acetate/hexane (gradient from 0% to 100%)

Sources & evidence

ORD record
ord-a7287209ff14408bb52132b2c5a0eaf3
Source dataset
uspto-grants-2014_05
Patent number
US08716482B2

Reaction notes

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