반응 #2286323
ord-ffed6f56b448476484dc8e42dfefe08c
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후처리
- 1온도The reaction was then heated to 90° C. for 1 h
- 2온도At this time, the reaction was cooled to 25° C.
- 3추출This mixture was extracted with ethyl acetate (200 mL)
- 4세척The organics were washed with a saturated aqueous sodium chloride solution (100 mL)
- 5건조dried with magnesium sulfate
- 6여과filtered
- 7농축concentrated under vacuum
실험 절차
A solution of [2,6-dibromo-4-(tetrahydro-pyran-2-yloxymethyl)-phenyl]-acetonitrile (60) (1.52 g, 3.91 mmol) in N,N-dimethylformamide (9 mL) at 25° C. was treated with sodium hydride (192.8 mg, 4.82 mmol, 60% dispersion in mineral oil). The reaction mixture was stirred at 25° C. for 10 min. At this time, the reaction was treated with a solution of 3,6-dichloro-4-isopropyl-pyridazine (7) (810 mg, 4.24 mmol) in N,N-dimethylformamide (2 mL). The reaction was then heated to 90° C. for 1 h. At this time, the reaction was cooled to 25° C., diluted with water (50 mL), a saturated aqueous sodium chloride solution (50 mL) and a saturated aqueous sodium bicarbonate solution (20 mL). This mixture was extracted with ethyl acetate (200 mL). The organics were washed with a saturated aqueous sodium chloride solution (100 mL), dried with magnesium sulfate, filtered, and concentrated under vacuum. Isco chromatography (120 g, Silica, 2:1 hexanes/ethyl acetate) afforded (6-chloro-5-isopropyl-pyridazin-3-yl)-[2,6-dibromo-4-(tetrahydro-pyran-2-yloxymethyl)-phenyl]-acetonitrile (61) (964 mg, 65%) as an orange viscous oil; LRMS for C21H22Br2ClN3O2 (M+H) at m/z=542. Molecular Weight=543.6894; Exact Mass=540.9767