Acetonitrile → 3-Bromo-4-{4-[4-(tert-butyldimethylsilanyloxy)butyl]imidazol-1-ylmethyl}benzonitrile

HRID 1877971Notes

Reaction equation

HRID 1877971 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[N:14]=[CH:15][N:16](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:17]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(#N)C.[Br:40][C:41]1[CH:42]=[C:43]([CH:46]=[CH:47][C:48]=1[CH2:49]Br)[C:44]#[N:45]>C(OCC)(=O)C>[Br:40][C:41]1[CH:42]=[C:43]([CH:46]=[CH:47][C:48]=1[CH2:49][N:16]1[CH:17]=[C:13]([CH2:12][CH2:11][CH2:10][CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[N:14]=[CH:15]1)[C:44]#[N:45]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 2884363-Bromo-4-(bromomethyl)benzonitrileHCID 668860904-[4-(tert-butyldimethylsilanyloxy)butyl]-1-trityl-1H-imidazole

Product 1

HCID 668975903-Bromo-4-{4-[4-(tert-butyldimethylsilanyloxy)butyl]imidazol-1-ylmethyl}benzonitrile

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

To 4-[4-(tert-butyldimethylsilanyloxy)butyl]-1-trityl-1H-imidazole (3.95 g, 7.95 mmol) is added acetonitrile (300 mL). To this solution is added 3-bromo-4-bromomethylbenzonitrile (2.14 g, 7.78 mmol). The solution is stirred at 40° C. for 18 h. The solvent is then removed in vacuo and methanol (300 ml) is added. The solution is heated to 55° C. and stirred for 1.5 h. Saturated sodium bicarbonate is then added and stirred for 10 min. The organic solvent is removed in vacuo, and the crude product extracted into ethyl acetate and washed with water. The organic solvent is removed in vacuo to give the crude product. Chromatography (silica gel, 1:0 to 1:1 to 0:1 hexanes:ethyl acetate) gives the pure product. MS (ESI) m/z 448, 450 (M+H).

Workup

  1. customThe solvent is then removed in vacuo and methanol (300 ml)
  2. additionis added
  3. temperatureThe solution is heated to 55° C.
  4. stirringstirred for 1.5 h
  5. additionSaturated sodium bicarbonate is then added
  6. stirringstirred for 10 min
  7. customThe organic solvent is removed in vacuo
  8. extractionthe crude product extracted into ethyl acetate
  9. washwashed with water
  10. customThe organic solvent is removed in vacuo
  11. customto give the crude product

Sources & evidence

ORD record
ord-2261d0b090094bfeb3f68cecf8145855
Source dataset
uspto-grants-2012_11
Patent number
US08314097B2

Reaction notes

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