Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 52727-57-8, name is Methyl 2-amino-5-bromobenzoate, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks
[3-F [ (4-CHLOROPHENYL)] (methyl) amino] [SULFONYL}-2-METHYLBENZOATE] (404 mg, 1.19 mmol) was suspended in dry [CH2C12] (10 mL) and DMF (10 [. L) UNDER N2.] The solution was treated with oxalyl chloride (Aldrich, 0.192 mL, 2.2 mmol) and stirred while gas evolved. After one hour the excess solvent and oxalyl chloride were evaporated and the resultant residue was taken up in dry [CH2C12] (10 mL). [METHYL-2-AMINO-5-] bromobenzoate (Aldrich, 230 mg, 1.0 mmol) was added as a solution in pyridine (3 mL) and the amber solution stirred at RT. After 2 hours [HPLC] indicated the reaction was complete. The mixture was diluted with CH2Cl2 (100 [ML)] and washed 2x with 1. OM HC1 followed by brine (100 mL each). The organic layer was evaporated and purified on a Biotage Flash 25M+ (40 g) silica cartridge using [CH2C12.] The combined fractions were evaporated and the product was dried under vacuum at [100 C] to afford 535mg (97%) of a glass-like [SOLID. 1H NMR] (400 MHz, DMSO-d6) 8 10.88 (s, 1 H), 8.05 (d, J= 8.9 Hz, [1] H), 7.99 (d, J= 2.3 Hz, 1 H), 7.93 (D, J= 7.5 Hz, 1 H), 7.86 (dd, J= 8.8, 2.4 Hz, 1 H), 7.80 (d, J= 7.3 Hz, 1 H), 7.57 (t, J= 7.9 Hz, 1 H), 7.45 (d, [J=8. 7HZ, 2H),] 7.29 (d, [J=8. 7HZ, 2H),] 3.83 (s, [3H),] 3.24 (s, [3H),] 2. [39] (s, [3 H).] 322 mg of the methyl ester solid was dissolved in hot dioxane (10 mL), and after cooling was treated with 1. OM [LIOH] (1.0 [ML,] 1.0 [MMOL).] After stirring overnight at RT the reaction was complete by [HPLC] and OAMS showed correct [M/Z] for the product. The solvent was evaporated and the residue was poured into 1. OM HC1 (100 mL) to afford a white precipitate. The product was extracted into EtOAc (125 [ML)] and washed 3x with [1.] OM HCl, and lx with brine (100 mL each). The organic layer was dried over [NA2S04,] filtered and evaporated to dryness. The crude product was re- [ CRYSTALLIZEDFROMHOTMEOH/ETOH. THERESULTANTPRODUCTWAS DRIEDAT 100 CUNDER] vacuum to afford 213 mg (68%) of white [CRYSTALS. 1H] NMR (400 MHz, DMSO-d6) [B] 11. [35] (s, 1 H), 8. [39] (d, [J=] 8.9 Hz, 1 H), 8.07 (d, [J=] 2.5 Hz, 1 H), 7.92 (dd, [J=] 8.1, 1. [0 HZ, 1 H),] 7.81-7. 89 (m, 2 H), 7.56 (t, [J= 7. 8 HZ, 1 H),] 7.41-7. 48 (m, 2 H), 7.24- 7.34 (m, 2 H), 3.23 (s, 3 H), 2.39 (s, [3 H).]
The synthetic route of 52727-57-8 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; PHARMACIA & UPJOHN COMPANY; WO2004/18414; (2004); A2;,
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