As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 15862-50-7, name is 3-Bromo-2-methoxy-5-nitropyridine, molecular formula is C6H5BrN2O3, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. name: 3-Bromo-2-methoxy-5-nitropyridine
Under 2 atmosphere, to a suspension of 3-bromo-2-methoxy-5- nitropyridine (5.00 g, 21.5 mmol, 1.00 equiv) and 5% Rh/C (0.123 g, 0.30 mol% Rh) in THF (107 mL, 0.200 M) hydrazine monohydrate (1.56 g, 25.8 mmol, 1.20 equiv) was added dropwise. The reaction mixture was monitored via TLC using EtOAc : hexanes 1:1 (v/v) as an eluent 15 until the disappearance of the starting 3-bromo-2-methoxy-5- nitropyridine (R/ = 0.90 (EtOAc : hexanes 1:1 (v/v)) and the appearance of the hydroxylamine intermediate (Rf = 0.61 (EtOAc : hexanes 1:1 (v/v)). Subsequently, sodium bicarbonate (2.14 g, 25.8 mmol, 1.20 equiv) was added to the reaction mixture followed by a solution of 20 methyl chloroformate (2.42 g, 25.75 mmol, 1.20 equiv) in THF (6.58 mL, 0.200 M) via a syringe pump (at a rate of 10.0 mL/h) . After the addition was complete, the reaction mixture was filtered through a short pad of celite and the celite was washed with EtOAc. The organic layers were combined and concentrated in vacuo. The residue was 25 purified by chromatography on silica gel, eluting with EtOAc : hexanes (3:7 to 1:1 (v/v)), to afford the title compound as a slightly light yellow solid (3.82 g, 13.8 mmol, 64% yield). Ri = 0.54 (EtOAc: hexanes 1:1 (v/v) ) . NMR Spectroscopy: XH NMR (500 MHz, (CD3)2SO, 25 C, delta) : 10.60 (s, 1H) 8.29 (d, J= 2.44 Hz, 1H) 8.13 (d, J = 2.44 Hz, 1H) 3.93 (s, 3H) 3.74 (s, 3H) . 13C NMR (125 MHz, (CD3)2SO, 25 C, delta) : 156.97, 155.40, 138.89, 135.74, 134. 47, 105.44, 5 55.01, 53.67. Mass Spectrometry: HRMS (ESI-TOF) (m/z) : calcd for C8Hi0BrN2O4 ([M + H]+), 276.9818, found, 276.9821.
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Reference:
Patent; THE RESEARCH FOUNDATION FOR THE STATE UNIVERSITY OF NEW YORK; NGAI, Ming-Yu; HOJCZYK, Katarzyna, N.; (214 pag.)WO2016/57931; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem