Electric Literature of 54916-66-4, 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. 54916-66-4, name is 5-Bromo-2-methoxynicotinic acid, molecular formula is C7H6BrNO3, 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.
To a solution of 5-bromo-2-methoxynicotinic acid (15 g, 64.6 mmol, commercially available from, for example, Combiblocks) in DCM (100 mL) cooled to 0 C, was added oxalyl dichloride (16.98 mL,194.0 mmol) followed by the slow addition of DMF (5.01 mL, 64.6 mmol) at 0 C. The reaction mixture was then stirred for 18 h at rt. A small aliquot of the reaction mixture was taken and quenched with MeOH, the TLC shows the complete conversion of SM. The reaction mixture was then concentrated and re-dissolved in DCM (150 mL) and treated with ethanamine hydrochloride (7.91 g, 97 mmol). The reaction mixture was stirred for 3 h at rt. After the reaction, water was added andthe organics extracted with ethyl acetate (2 x 300 mL). The organic layer was separated, dried over Na2504, filtered and concentrated to obtain the crude product. The crude product was purified by column chromatography on a silica gel 100-200 column and was eluted with l6% EtOAc/n-hexane. The collected pure fractions were concentrated under reduced pressure to afford the desired product 5-bromo-N-ethyl-2-methoxynicotinamide (11 g, 41.0 mmol, 64 % yield) as an off-whitesolid.LCMS (10 mm RND-FA-10-MIN): Rt = 4.22 mi [MH] = 261.LCMS Conditions: RND-FA- lO-MIN:Column: Acquity BEH C18 (100 mm x 2.1 mm, 1.7 pm) Mobile Phase: A: 0.05% formic acid in ACN; B: 0.05% formic acid in waterTime (mm) /%B: 0/97, 0.4/97, 7.5/2, 9.5/2, 9.6/97, 10/97Column Temp: 35 C, Flow Rate: 0.45 mL/min
According to the analysis of related databases, 54916-66-4, the application of this compound in the production field has become more and more popular.
Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ATKINSON, Stephen John; DEMONT, Emmanuel Hubert; HARRISON, Lee Andrew; HAYHOW, Thomas George Christopher; HOUSE, David; LINDON, Matthew J; PRESTON, Alexander G; SEAL, Jonathan Thomas; WALL, Ian David; WATSON, Robert J; WOOLVEN, James Michael; (141 pag.)WO2017/50714; (2017); A1;,
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