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| CAS No. : | 1178884-53-1 | MDL No. : | MFCD21364605 |
| Formula : | C5H4BrClN2O | Boiling Point : | - |
| Linear Structure Formula : | - | InChI Key : | N/A |
| M.W : | 223.46 | Pubchem ID : | 59216474 |
| Synonyms : |
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| TPSA :Topological Polar Surface Area | - | H-Bond Acceptor Count : | - |
| XLogP3 : | - | H-Bond Donor Count : | - |
| SP3 : | - | Rotatable Bond Count : | - |
| Signal Word: | Warning | Class | N/A |
| Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
| Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
| GHS Pictogram: |
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[ 74-88-4 ]
[ 1178884-53-1 ]| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 79% | With caesium carbonate In N,N-dimethyl-formamide for 3.33 h; | Step 3: To a solution of 4-bromo-6-chloropyridazin-3(2H)-one (1.0 equiv.) and Cs2CO3 (1.2 equiv.) in DMF (0.07 M) was added iodomethane (1.5 equiv.) drop-wise over 20 min. The resulting mixture was stirred for 3 h. The reaction mixture was then diluted with ammonium chloride, then extracted with ethyl acetate, dried over MgSO4 and concentrated in vacuo to yield as a brown solid. The oil was further purified via silica gel column chromatography eluting with 100percent heptanes to 80percent ethyl acetate:heptanes to yield 4-bromo-6-chloro-2-methylpyridazin-3(2H)-one as an off-white solid in 79percent yield. LCMS (m/z) (M+H)=222.9/224.9, Rt=0.54 min. 1H NMR (400 MHz, ) δ ppm 3.77-3.86 (m, 3H) 7.56-7.69 (m, 1H). |
| 68% | Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.17 h; Inert atmosphere Stage #2: at 20℃; for 1.50 h; |
A 250-mL single-necked round bottomed flask equipped with a magnetic stirrer was purged with nitrogen and charged with 4-bromo-6-chloropyridazin-3(2H)-one (1.00 g, 4.77 mmol) and DMF (15 mL). Sodium hydride (60percent by weight in oil, 229 mg, 5.73 mmol) was added in one portion. After stirring at room temperature for 10 minutes, iodomethane (1.02 g, 7.16 mmol) was added and the reaction stirred at room temperature for 1.5 h. The reaction was then quenched with aqueous saturated sodium bicarbonate (10 mL) and the resulting solution poured into water (150 mL). The mixture was then extracted with ethyl acetate (250 mL). The organic layer was dried over sodium sulfate. The drying agent was then removed by filtration, and the filtrate was concentrated under reduced pressure to residue. Purification by column chromatography afforded 103e in a 68percent yield (722 mg) as a white solid: mp 107- 108 °C; ]H NMR (300 MHz, CDC13) δ 7.62 (s, 1H), 3.81 (s, 3H). |
| 68% | Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.17 h; Stage #2: at 20℃; for 1.50 h; |
A 250-mL single-necked round bottomed flask equipped with a magnetic stirrer was purged with nitrogen and charged with 4-bromo-6-chloropyridazin-3(2H)-one (1.00 g, 4.77 mmol) and DMF (15 mL). Sodium hydride (60percent by weight in oil, 229 mg, 5.73 mmol) was added in one portion. After stirring at room temperature for 10 minutes, iodomethane (1.02 g, 7.16 mmol) was added and the reaction stirred at room temperature for 1.5 h. The reaction was then quenched with aqueous saturated sodium bicarbonate (10 mL) and the resulting solution poured into water (150 mL). The mixture was then extracted with ethyl acetate (250 mL). The organic layer was dried over sodium sulfate. The drying agent was then removed by filtration, and the filtrate was concentrated under reduced pressure to residue. Purification by column chromatography afforded 103a in a 68percent yield (722 mg) as a white solid: mp 107- 108 °C; ]H NMR (300 MHz, CDC13) δ 7.62 (s, 1H), 3.81 (s, 3H). |
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