Diethylamine → HCID 57781102, compound

HRID 1690748Notes

Reaction equation

HRID 1690748 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][C:11]1[N:12]=[CH:13][N:14](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Br[CH2:36][C:37]1[CH:44]=[CH:43][CH:42]=[CH:41][C:38]=1[C:39]#[N:40].C(NCC)C>C(#N)C>[Si:1]([O:8][CH2:9][CH2:10][C:11]1[N:12]([CH2:36][C:37]2[CH:44]=[CH:43][CH:42]=[CH:41][C:38]=2[C:39]#[N:40])[CH:13]=[N:14][CH:15]=1)([C:4]([CH3:5])([CH3:7])[CH3:6])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 895992-(Bromomethyl)benzonitrileHCID 668853594-(2-((tert-Butyldimethylsilyl)oxy)ethyl)-1-trityl-1H-imidazole

Product 1

HCID 57781102HCID 57781102, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-[2-(tert-butyldimethylsilanyloxy)-ethyl]-1-trityl-1H-imidazole (2.10 g, 4.48 mmol) in acetonitrile (20 mL) is added 2-bromomethylbenzonitrile (0.967 g, 4.93 mmol). The reaction mixture is stirred at 60° C. for 16 h. It is then cooled to room temperature and diethylamine (5 mL, 44.8 mmol) is added. The reaction mixture is stirred at 60° C. for 30 min. It is then cooled to room temperature and the solvents are removed in vacuo. Methanol (25 mL) is added and stirring is continued for 1 h at room temperature. Methanol is removed by concentration in vacuo. The residue is dissolved in ethyl acetate and washed with water twice. The combined organic phase is dried over Na2SO4 and concentrated in vacuo. The residue is purified by silica gel chromatography (dichloromethane-methanol, 19:1) to give 2-{5-[2-(tert-butyldimethylsilanyloxy)-ethyl]-imidazol-1-ylmethyl}-benzonitrile; MS (ESI) m/z 342 (M+H)

Workup

  1. temperatureIt is then cooled to room temperature
  2. stirringThe reaction mixture is stirred at 60° C. for 30 min
  3. temperatureIt is then cooled to room temperature
  4. customthe solvents are removed in vacuo
  5. additionMethanol (25 mL) is added
  6. stirringstirring
  7. waitis continued for 1 h at room temperature
  8. customMethanol is removed by concentration in vacuo
  9. dissolutionThe residue is dissolved in ethyl acetate
  10. washwashed with water twice
  11. dry with materialThe combined organic phase is dried over Na2SO4
  12. concentrationconcentrated in vacuo
  13. customThe residue is purified by silica gel chromatography (dichloromethane-methanol, 19:1)

Sources & evidence

ORD record
ord-e6c17ebfcabb4616bdc84f49286c30e1
Source dataset
uspto-grants-2012_04
Patent number
US08153674B2

Reaction notes

Loading…