Imidazole → HCID 89525790, compound

HRID 2278354Notes

Reaction equation

HRID 2278354 reaction equation
[Cl-].[Br:2][C:3]1[CH:4]=[C:5]([CH:8]([NH3+:11])[CH2:9][OH:10])[S:6][CH:7]=1.N1C=CN=C1.[CH3:17][C:18]([Si:21](Cl)([CH3:23])[CH3:22])([CH3:20])[CH3:19]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Br:2][C:3]1[CH:4]=[C:5]([CH:8]([NH2:11])[CH2:9][O:10][Si:21]([C:18]([CH3:20])([CH3:19])[CH3:17])([CH3:23])[CH3:22])[S:6][CH:7]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 89525783HCID 89525783, compound

Product 1

HCID 89525790HCID 89525790, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

1-(4-bromothiophen-2-yl)-2-hydroxyethanaminium chloride (300 mg, 1.35 mmol), imidazole (120 mg, 1.76 mmol), DMAP (8.25 mg, 0.068 mmol) and TEA (188 μL, 1.35 mmol) were dissolved in 13.5 mL DCM. TBSCl was then added (265 mg, 1.76 mmol) at 0° C. and the mixture was stirred for 48 hours at room temperature. The mixture was quenched with saturated NaHCO3 and the phases separated. The organic extract was concentrated and purified on silica gel (EtOAc/hexanes).

Workup

  1. customThe mixture was quenched with saturated NaHCO3
  2. customthe phases separated
  3. extractionThe organic extract
  4. concentrationwas concentrated
  5. custompurified on silica gel (EtOAc/hexanes)

Sources & evidence

ORD record
ord-322a0afa31774b29976d407a6b92b04a
Source dataset
uspto-grants-2015_09
Patent number
US09133157B2

Reaction notes

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