4-Iodo-1-tritylimidazole → 3-Fluoro-4-(5-iodo-imidazol-1-ylmethyl)benzonitrile

HRID 1877935Notes

Reaction equation

HRID 1877935 reaction equation
[I:1][C:2]1[N:3]=[CH:4][N:5](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:6]=1.Br[CH2:27][C:28]1[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[CH:30][C:29]=1[F:36]>>[F:36][C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][C:28]=1[CH2:27][N:3]1[C:2]([I:1])=[CH:6][N:5]=[CH:4]1)[C:32]#[N:33]

Participants

3

Reactant 2

HCID 6182524-Iodo-1-tritylimidazoleHCID 27831494-(Bromomethyl)-3-fluorobenzonitrile

Product 1

HCID 588272153-Fluoro-4-(5-iodo-imidazol-1-ylmethyl)benzonitrile

Procedure

A mixture of 4-iodo-1-trityl-1H-imidazole (17.1 g, 39.2 mmol) and 4-bromomethyl-3-fluorobenzonitrile (9.65 g, 45.08 mmol) in 150 mL of dry actetonitrile is stirred at room temperature for 7 days. After concentration, the residue is mixed with methanol, and heated to reflux for 1.5 h. The solvent is subsequently removed and the residue is treated with 1M HCl (300 mL). The resulting suspension is filtered and the washed with HCl (1M). The combined solution is adjusted to PH 9-10 by saturated NaHCO3 solution. The resulting precipitation is collected by filtration, dried in vacuum oven. MS (ESI) m/z (M+H) 328.1.

Workup

  1. concentrationAfter concentration
  2. additionthe residue is mixed with methanol
  3. temperatureheated
  4. temperatureto reflux for 1.5 h
  5. customThe solvent is subsequently removed
  6. additionthe residue is treated with 1M HCl (300 mL)
  7. filtrationThe resulting suspension is filtered
  8. washthe washed with HCl (1M)
  9. customThe resulting precipitation
  10. filtrationis collected by filtration
  11. customdried in vacuum oven

Sources & evidence

ORD record
ord-d109e669c20d461f85ddf495682f00df
Source dataset
uspto-grants-2012_11
Patent number
US08314097B2

Reaction notes

Loading…