Synthetic Route of 369-26-6, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 369-26-6, name is Methyl 3-amino-4-fluorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.
General procedure: To a 40 mL reaction vessel was charged 8-chloro-N-(2-fluorobenzyl)-N-(2- hydroxyethyl)-1-methyl-1,4-dihydrochromeno[4,3-c]pyrazole-3-carboxamide (I-73) (0.10 mmol) and CH2Cl2 (10 mL) followed by the addition of commercial Dess-Martin Periodinane (Sigma- Aldrich, 1,1,1-Tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H-one, 0.20 mmol) and buffered with solid sodium bicarbonate (0.20 mmol). The milky white suspension was rapidly stirred for 2 hrs and then the reaction was then directly diluted with ethyl acetate (150 mL) and washed with water (3 x 15 mL). The resulting organic extract was concentrated to a residue (in vacuo) and used directly without delay or further manipulation. The residue was dissolved in 9:1 MeOH/AcOH (5 mL) and treated with methyl-3-amino benzoate (0.40 mmol). The resulting reaction was then stirred at room temperature for 30 mins. and then treated with sodium cyanoborohydride (1.0 mmol, portion-wise over 30 mins.) followed by stirring at room temperature for an additional 1 hr. The resulting reaction was diluted with ethyl acetate (150 mL) and washed with water (3 x 25 mL). The resulting organic extracts were concentrated in vacuo and then directly subjected to reverse phase chromatography using TFA-modified (0.05 percent) water/ACN (35 to 80 percent). All fractions were reduced to dryness under vacuum and subjected to a free base event using polymer immobilized carbonate (SPE-C03H Varian cartridge, 0.90 nominal load with MeOH mobilizer, 10 mL) to give methyl 3-((2-(8-chloro-N-(2- fluorobenzyl)-1-methyl-1,4-dihydrochromeno[4,3-c]pyrazole-3-carboxamido)ethyl)amino) benzoate (63-lnt) as a white solid. 1H NMR (400 MHz, d4-MeOH): delta 7.48-7.19 (m, 8H), 7.03- 6.92 (3H), 7.18 (app d, J = 8.0 Hz, 1 H), 6.62 (app dt, J = 12.2, 8.0 Hz, 1 H), 5.30-5.20 (m, 2H), 4.83 (br s, 2H), 4.21 (t, J = 5.0 Hz, 2H), 3.85 (s, 3H), 3.74 (s, 3H), 3.38 (t, J = 5.0 Hz, 2H). Mixture of rotamers. MS (m/z): 549.2/551.2 (M+H)+(chlorine isotope pattern).
The synthetic route of Methyl 3-amino-4-fluorobenzoate has been constantly updated, and we look forward to future research findings.
Reference:
Patent; IRM LLC; CHIANELLI, Donatella; LIU, Xiaodong; MOLTENI, Valentina; NELSON, John; ROLAND, Jason; RUCKER, Paul; TULLY, David; WO2015/69666; (2015); A1;,
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