Diisobutylaluminumhydride → 6-(2,6-Dichloro-4-hydroxymethyl-benzyl)-4-isopropyl-pyridazin-3-one

A mixture of 3,5-dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-ylmethyl)-benzoic acid methyl ester (52) (160 mg, 0.45 mmol) in tetrahydrofuran (5 mL) at 25° C. was treated with a 1M solution of diisobutylaluminum hydride in tetrahydrofuran (2.7 mL, 2.7 mmol). The reaction was stirred at room temperature for 24 h. A TLC of the reaction indicated that starting material was still present. An additional amount of the 1 M solution of diisobutylaluminum hydride in tetrahydrofuran (1.0 mL) was added to the reaction. After stirring 30 min at room temperature, the reaction was cautiously quenched by addition to a 1:1 mixture of a saturated aqueous sodium chloride solution (30 mL) and a 2N aqueous hydrochloric acid solution (30 mL). The mixture was extracted with ethyl acetate (3×50 mL). The organic layers were combined, washed with a saturated aqueous sodium chloride solution (20 mL), dried with magnesium sulfate, filtered and concentrated under vacuum. The resulting solid was dried under high vacuum to afford 6-(2,6-dichloro-4-hydroxymethyl-benzyl)-4-isopropyl-pyridazin-3-one (53) (168 mg) as a brown solid that was used without further purification; LRMS-ES(+) for C15H16Cl2N2O2 (M+H) m/z=327. MW=327.2130, Exact Mass=326.0589

1. stirringAfter stirring 30 min at room temperature
2. customthe reaction was cautiously quenched by addition to a 1:1 mixture of a saturated aqueous sodium chloride solution (30 mL)
3. extractionThe mixture was extracted with ethyl acetate (3×50 mL)
4. washwashed with a saturated aqueous sodium chloride solution (20 mL)
5. dry with materialdried with magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated under vacuum
8. customThe resulting solid was dried under high vacuum

ORD record

ord-2d9ad3320eb34c8f9a830cd135a5c1c5

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

USRE046024E1