Tetrabutylammonium Fluoride → HCID 86650552, compound

Tetra-n-butylammonium fluoride (13.0 mL of a 1M solution in THF, 13.0 mmol) was added dropwise to a stirred solution of silyl ether 189 (6.78 g, 12.3 mmol) in anhydrous THF (140 mL) and the mixture was stirred at room temperature for 4 h. The resulting solution was concentrated under reduced pressure, and then diluted with ice-water (120 mL) and extracted with EtOAc (5×120 mL). The extracts were washed with brine (100 mL) and then evaporated to dryness and the residue was chromatographed on silica gel. Elution with 0-80% Et2O/petroleum ether, petroleum ether and 0-1% MeOH/CH2Cl2 firstly gave foreruns, and then further elution with 2-3% MeOH/CH2Cl2 gave 3-(2-bromo-4-nitro-1H-imidazol-1-yl)-2-{[(6-bromo-3-pyridinyl)oxy]methyl}-1-propanol (190) (5.36 g, 100%) as a pale yellow foam; 1H NMR (CDCl3) δ 8.07 (d, J=3.0 Hz, 1H), 7.89 (s, 1H), 7.40 (d, J=8.7 Hz, 1H), 7.09 (dd, J=8.7, 3.2 Hz, 1H), 4.32 (d, J=7.2 Hz, 2H), 4.09 (d, J=5.5 Hz, 2H), 3.87 (dd, J=10.7, 4.7 Hz, 1H), 3.75 (dd, J=10.8, 4.8 Hz, 1H), 2.57 (m, 1H); HRESIMS calcd for C12H13Br2N4O4 z [M+H]+ 438.9258, 436.9278, 434.9298. found 438.9262, 436.9279, 434.9299.

1. concentrationThe resulting solution was concentrated under reduced pressure
2. additiondiluted with ice-water (120 mL)
3. extractionextracted with EtOAc (5×120 mL)
4. washThe extracts were washed with brine (100 mL)
5. customevaporated to dryness
6. customthe residue was chromatographed on silica gel
7. washElution with 0-80% Et2O/petroleum ether, petroleum ether and 0-1% MeOH/CH2Cl2 firstly gave foreruns
8. washfurther elution with 2-3% MeOH/CH2Cl2

ORD record

ord-d557c118092845d1953111005c5690f8

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08293734B2