Triethylamine → 1-(4-bromo-2-fluorobenzyl)-2-(n-propyl)-4-ethyl-5-(1-(trimethylsilyloxy)ethenyl)-1H-imidazole

HRID 1078047Notes

Reaction equation

HRID 1078047 reaction equation
[Br:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][N:7]2[C:11]([C:12](=[O:14])[CH3:13])=[C:10]([CH2:15][CH3:16])[N:9]=[C:8]2[CH2:17][CH2:18][CH3:19])=[C:4]([F:22])[CH:3]=1.O([Si:31]([CH3:34])([CH3:33])[CH3:32])S(C(F)(F)F)(=O)=O.C(N(CC)CC)C>C1COCC1.C(OCC)C>[Br:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][N:7]2[C:11]([C:12]([O:14][Si:31]([CH3:34])([CH3:33])[CH3:32])=[CH2:13])=[C:10]([CH2:15][CH3:16])[N:9]=[C:8]2[CH2:17][CH2:18][CH3:19])=[C:4]([F:22])[CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 65367Trimethylsilyl triflateHCID 194304311-(4-bromo-2-fluorobenzyl)-2-(n-propyl)-4-ethyl-5-acetyl-1H-imidazole

Product 1

HCID 194304391-(4-bromo-2-fluorobenzyl)-2-(n-propyl)-4-ethyl-5-(1-(trimethylsilyloxy)ethenyl)-1H-imidazole

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
22 °C

Procedure

To a solution of 2.50 g (6.81 mmol) of 1-(4-bromo-2-fluorobenzyl)-2-(n-propyl)-4-ethyl-5-acetyl-1H-imidazole (67 R1 =2-F, R2 =4-Br, n=0; prepared using the procedures of Example 3, Parts A and B) in 80 mL anhydrous THF was added 7.59 mL trimethylsilyl triflate (40.8 mmol) under nitrogen at 22° C., followed by 11.38 mL (81.9 mmol) triethylamine. The mixture was stirred at 22° C. for 2.5 hours and then diluted with 100 mL of anhydrous ethyl ether and quenched with 10 mL of saturated NaHCO3 solution. The organic layer was washed with saturated NaHCO3 solution, dried over Na2SO4, and filtered. Solvents were then removed under reduced pressure yield 2.69 g (90%) of the title compound as a brown oil, which was used without further purification. 1H NMR (300 MHz, CDCl3): δ 0.14 (s, 9H); 0.84 (t, 3H); 1.16 (t, 3H); 1.68 (m, 2H); 2.41 (t, 2H); 2.56 (q, 2H); 4.30 (s, 1H); 4.43 (s, 1H); 5.03 (s, 2H); 6.44 (t, 1H); 7.10 (m, 2H). ##STR103##

Workup

  1. customprepared
  2. customquenched with 10 mL of saturated NaHCO3 solution
  3. washThe organic layer was washed with saturated NaHCO3 solution
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customSolvents were then removed under reduced pressure yield 2.69 g (90%) of the title compound as a brown oil, which
  7. customwas used without further purification

Sources & evidence

ORD record
ord-baa2e554a73841fcbeee9cbc72d6d7da
Source dataset
uspto-grants-1996_08
Patent number
US05545651

Reaction notes

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