Sodium hydride → 2,5-Dibromo-1-{[2-(dimethylsilyl)ethoxy]methyl}-1H-imidazole

Temperature

0 °C

To a stirred solution of 2,5-dibromo-1H-imidazole (1 eq.) in DMF at 0° C. under Ar was added NaH (1.2 eq.) and the mixture stirred for 30 min at 0° C. Then SEM-Cl (1.1 eq.) was added dropwise, and the mixture stirred 16 h warming to RT. The reaction was quenched by slow addition of H2O and the desired product was extracted with EtOAc. The organic layer was washed with brine, dried (Na2SO4) and concentrated under reduced pressure. The crude was purified by column chromatography eluting with 10% EtOAc/Petroleum ether to afford the desired product. 1H NMR (300 MHz, CD3CN) δ: 7.10 (1H, s), 5.21 (2H, s), 3.53 (2H, t, J=7.3 Hz), 0.90 (2H, t, J=7.3 Hz), 0.10 (9H, s). MS (ES) C9H16Br2N2OSi requires: 354:356:358 [1:2:1], found: 355:357:359 [1:2:1] (M+H)+.

1. stirringthe mixture stirred 16 h
2. temperaturewarming to RT
3. customThe reaction was quenched by slow addition of H2O
4. extractionthe desired product was extracted with EtOAc
5. washThe organic layer was washed with brine
6. dry with materialdried (Na2SO4)
7. concentrationconcentrated under reduced pressure
8. customThe crude was purified by column chromatography
9. washeluting with 10% EtOAc/Petroleum ether

ORD record

ord-f9addf09ea474f87b31a2401b0f721b8

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07863294B2