Imidazole → HCID 71284770, compound

HRID 1481804Notes

Reaction equation

HRID 1481804 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([CH2:11][OH:12])[NH:8]2)=[CH:4][CH:3]=1.[Si:13](Cl)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].N1C=CN=C1>CN(C=O)C>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([CH2:11][O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[NH:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 13567957(6-Bromo-1H-indol-2-yl)methanol

Product 1

HCID 71284770HCID 71284770, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product from Step 1 (1.87 g, 8.3 mmol) was combined with t-butyldimethylsilyl chloride (1.38 g, 9.1 mmol) and imidazole (734 mg, 10.8 mmol) in DMF (15 mL). The mixture was stirred 2 h at room temperature. The solvents were removed by rotary evaporation under reduced pressure. The resulting residue was partitioned in EtOAc and saturated aqueous ammonium chloride. The organic layer was washed with brine, dried over Na2SO4, concentrated and chromatographed on silica gel (0-15% EtOAC in hexanes) to give the product (2.7 g, 96%). LC-MS 340.2, 342.2 [M+H]+, RT 1.62 min.

Workup

  1. customThe solvents were removed by rotary evaporation under reduced pressure
  2. customThe resulting residue was partitioned in EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customchromatographed on silica gel (0-15% EtOAC in hexanes)

Sources & evidence

ORD record
ord-caa577946f844d03963eb5f7217915a2
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

Loading…