5-BroMo-4-[2-(diMethylaMino)ethenyl]-2-Methoxy-3-nitropyridine synthesis
- Product Name:5-BroMo-4-[2-(diMethylaMino)ethenyl]-2-Methoxy-3-nitropyridine
- CAS Number:917918-81-1
- Molecular formula:C10H12BrN3O3
- Molecular Weight:302.12
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Yield:917918-81-1 92%
Reaction Conditions:
in N,N-dimethyl-formamide at 80 - 95; for 9 h;
Steps:
In a 500 mL round-bottomed flask equipped with a stir bar and addition funnel was added 3 (22 g, 89 mmol, 1 eq.) and DMF (178 mL) then heated to 80 °C. DMF-DMA (104 mL, 736 mmol, 8.26 eq.) was added via addition funnel over 5 minutes then heated to 95 °C for 9 hours until full consumption of 3. The reaction was cooled to room temperature then poured into 500 mL of ice-cold water (red solid crashed out). The solid was filtered through a sintered glass funnel while rinsing with ice-cold water (100 mL) and the collected solid was dried under vacuum to give 4 (24.8 g, 82.0 mmol, 92% yield) as a red solid. (0186) TLC: Rf = 0.62 (20% EtOAc in hexanes) (0187) 3H NMR: (600 MHz, CDCh) d 8.11 (s, 1H), 6.99 (d, J = 13.7 Hz, 1H), 4.91 (d, J = 13.6 Hz, 1H), 3.94 (s, 3H), 2.91 (s, 7H) ppm. (0188) 13C NMR: (151 MHz, CDCL) d 154.66, 148.20, 147.21, 139.78, 131.36, 111.69, 87.60, 54.39, 40.52 ppm
References:
WO2022/115753,2022,A1 Location in patent:Page/Page column 42
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