Dimethylformamide → HCID 22018610, compound

HRID 7117Notes

Reaction equation

[Br:1][C:2]1[C:3]([O:21][CH3:22])=[C:4]([C:8]2[N:12]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH:11]=[N:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[Li]CCCC.CN([CH:31]=[O:32])C>>[Br:1][C:2]1[C:3]([O:21][CH3:22])=[C:4]([C:8]2[N:12]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:18])([CH3:20])[CH3:19])[C:11]([CH:31]=[O:32])=[N:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 220186555-(3-bromo-2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole

HCID 178418339Butyllithium

Product 1

HCID 22018610HCID 22018610, compoundYield 47%

Procedure

Reaction 5-(3-bromo-2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole (485 mg, 1.26 mmol), 2.5 M n-BuLi (828 uL, 2.07 mmol), and DMF (494 uL, 6.38 mmol) for 2 h at −40° C. followed by column chromatography on silica gel (EtOAc/hexane 9:1) gave the title compound (240 mg, 47%) as a yellow oil. 1H NMR (300 MHz, CDCl3) δ 0.00 (s, 9H), 0.94 (t, 2H, J=9.0 Hz), 3.61 (t, 2H, J=7.5 Hz), 3.93 (s, 3H), 5.83 (s, 2H), 6.86 (d, 1H, J=9.0 Hz), 7.38 (dd, 1H, J=9.0, 3.0 Hz), 7.94 (s, 1H), 8.38 (d, 1H, J=3.0 Hz), 9.89 (s, 1H). ES-MS m/z 413 (M+H).

Sources & evidence

ORD record: ord-190fd705a6c045a0847e973b190773f6
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07084155B2

Reaction notes

Loading…