tert-Butyldimethylsilyl trifluoromethanesulphonate → HCID 58204929, compound

HRID 886062Notes

Reaction equation

HRID 886062 reaction equation
[I:1][C:2]1[N:3]=[CH:4][N:5]([CH2:7][C:8]([CH3:11])([OH:10])[CH3:9])[CH:6]=1.O([Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])S(C(F)(F)F)(=O)=O>N1C(C)=CC=CC=1C>[Si:20]([O:10][C:8]([CH3:11])([CH3:9])[CH2:7][N:5]1[CH:6]=[C:2]([I:1])[N:3]=[CH:4]1)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 58204348HCID 58204348, compound

Product 1

HCID 58204929HCID 58204929, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 79372,6-LutidineSolvent

Conditions

Temperature
0 °C

Procedure

1-(4-iodo-1H-imidazol-1-yl)-2-methylpropan-2-ol was dissolved in DCm and lutidine was added dropwise at 0° C. The mixture was stirred at 0° C. for 30 min then tert-butyldimethylsilyl triflate (TBSOTf) was added dropwise. The mixture was warmed to room temperature and sitted for about an hour, then quenched with 30% acetic acid, extracted ethylacetate, dried, and concentrated to give 1-(2-(tert-butyldimethylsilyloxy)-2-methylpropyl)-4-iodo-1H-imidazole (Yield=74%). LC-MS: m/z=381[M+H+]

Workup

  1. additionwas added dropwise at 0° C
  2. temperatureThe mixture was warmed to room temperature
  3. waitsitted for about an hour
  4. customquenched with 30% acetic acid
  5. extractionextracted ethylacetate
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-91646e92eb7f4e658b8a191a7ea3390b
Source dataset
uspto-grants-2012_08
Patent number
US08242104B2

Reaction notes

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