Sodium hydride → 5-(3-bromo-2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole

HRID 983602Notes

Reaction equation

HRID 983602 reaction equation
[Br:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([C:8]2[NH:12][CH:11]=[N:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[CH3:17][Si:18]([CH2:21][CH2:22][O:23][CH2:24]Cl)([CH3:20])[CH3:19]>>[Br:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([C:8]2[N:12]([CH2:24][O:23][CH2:22][CH2:21][Si:18]([CH3:20])([CH3:19])[CH3:17])[CH:11]=[N:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 220185934-(3-bromo-2-methoxyphenyl)-1H-imidazole

Product 1

HCID 220186555-(3-bromo-2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazoleYield 60%

Procedure

Reaction of 5-(3-bromo-2-methoxy-phenyl)-1H-imidazole (539 mg, 3.10 mmol), NaH (60%, 120 mg, 3.00 mmol), and SEMCl (751 uL, 3.61 mmol) followed by column chromatography on silica gel (hexane/EtOAC 3:2) gave the title compound (485 mg, 60%) as a brown oil. 1H NMR (300 MHz, CDCl3) δ0.00 (s, 9H), 0.93 (t, 2H, J=7.5 Hz), 3.52 (t, 2H, J=7.5 Hz), 3.93 (s, 3H), 5.31 (s, 2H), 6.82 (d, 1H, J=6.0 Hz), 7.31 (dd, 1H, J=9.0, 3.0 Hz), 7.63 (s, 1H), 7.66 (s, 1H), 8.36 (d, 1H, J=2.1 Hz). ES-MS m/z 385 (M+H).

Sources & evidence

ORD record
ord-00523f6a67bd40ebbdc3848112ae352b
Source dataset
uspto-grants-2005_03
Patent number
US06864265B2

Reaction notes

Loading…