Application of 57381-59-6, These common heterocyclic compound, 57381-59-6, name is Methyl 5-bromo-2-fluorobenzoate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
Sequentially add tri-tert-butylphosphine (88 mg, 0. 437 mmol) in anhydrous 1, 4- dioxane (1 mL), diisopropylethylamine (1. 5 mL, 8. 74 mmol), 5-bromo-2-fluorobenzoic acid methyl ester, (prepared as described in PREPARATION 42), (1. 69 g, 7. 28 mmol) and a solution of 5-ethynylnicotinonitrile, (prepared as described in PREPARATION 4), (0. 93 g, 7. 28 mmol) in anhydrous 1, 4-dioxan (4 mL), to a stirring mixture of dichloro (benzonitrile) palladium (II) (84 mg, 0. 218 mmol) and copper (I) iodide (28 mg, 0. 146 mmol) in anhydrous 1, 4-dioxan (1 mL) under nitrogen. Stir for 2 h and concentrate. Purify the residue twice by silica gel chromatography, eluting with 10 : 90 ethyl acetate : hexanes, to give the title compound as a white solid (0. 9 g, 44%). 1H NMR (400 MHz, CDCl3) 6 1. 48 (s, 3H), 3. 87 (s, 3H), 7. 07-7. 12 (m, 1H), 7. 58-7. 62 (m, 1H), 7. 96-7. 98 (m, 1H), 8. 06 (dd, J = 2. 7 Hz, J = 6. 5 Hz, 1H), 8. 74 (br s, lH), 8. 84 (br s, 1H) ; MS (ES) : m/z = 280. 9 [M+H] +.
The synthetic route of 57381-59-6 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; ELI LILLY AND COMPANY; WO2005/94822; (2005); A1;,
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