Imidazole → HCID 67471170, compound

HRID 2408478Notes

Reaction equation

HRID 2408478 reaction equation
[Br:1][C:2]1[S:6][C:5]([CH2:7][OH:8])=[N:4][N:3]=1.CN(C=O)C.N1C=CN=C1.[CH3:19][CH:20]([Si:22](Cl)([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])[CH3:21]>CCOC(C)=O>[Br:1][C:2]1[S:6][C:5]([CH2:7][O:8][Si:22]([CH:26]([CH3:28])[CH3:27])([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:21])[CH3:19])=[N:4][N:3]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 139400Triisopropylsilyl chlorideHCID 633840781,3,4-Thiadiazole-2-Methanol, 5-broMo-

Product 1

HCID 67471170HCID 67471170, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A 500 mL (one neck) round-bottom flask with a stir bar, septum and needle inlet was charged with (5-bromo-[1,3,4]thiadiazol-2-yl)-methanol (25 g, 128 mmol), DMF (250 mL), imidazole (17.9 g, 263 mmol, 2 equiv.) and TIPSCl (30.0 g, 155 mmol, 1.2 equiv.). The solution was stirred for 5 hours and diluted with EtOAc. The solution was washed with HCl (1N, 2×) and brine. The organic layer was dried over Na2SO4 and concentrated. The crude product was purified by silica gel chromatography (0-10% EtOAc/Hex) to provide 2-bromo-5-triisoproylsilanyloxymethyl-[1,3,4]thiadiazole (44.1 g, 98%).

Workup

  1. washThe solution was washed with HCl (1N, 2×) and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe crude product was purified by silica gel chromatography (0-10% EtOAc/Hex)

Sources & evidence

ORD record
ord-3cf2207104d84a4a90efb9372d146265
Source dataset
uspto-grants-2014_08
Patent number
US08815858B2

Reaction notes

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