Application of 445-02-3, A common heterocyclic compound, 445-02-3, name is 4-Bromo-2-(trifluoromethyl)aniline, molecular formula is C7H5BrF3N, 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.
To a mixture of 2-amino-5-bromobenzotrifluoride (1.0 g, 4.17 mmol) in DCM (10 mL) at 0-5C was added NEt3 (1.16 mL, 8.33 mmol), then methanesulfonyl chloride (0.389 mL, 5 mmol) dropwise. The reaction mixture was stirred at rt for 4 days. After 2 days, more NEt3 was added (1.16 mL, 8.33 mmol). As there was no evolution after 3 days, more NEt3 (0.580 mL, 4.17 mmol) and methanesulfonyl chloride (0.324 mL, 4.17 mmol) were added. The reaction was not completed, so the reaction mixture was then heated in a microwave oven at 1 10C for 20 min. There was no evolution, so the reaction was stopped. The reaction mixture was diluted with water and DCM. Layers were separated. The organic layer was washed with water, dried over MgS04 and evaporated. Purification by Flash chromatography using CombiFlash Companion ISCO system (Redisep silica 40g column, eluting with Cyclohexane/EtOAc 100:0 to 70:30) did not give the pure compound. Purification by prep HPLC using Gilson system (SunFire C18 column, eluting with H20 + 0.1 % TFA / CH3CN 20% to 85%) gave the title compound (404 mg, 31 % yield) as a white solid. 1H-NMR (400 MHz, DMSO-de, 298 K): delta ppm 3.12 (s, 3H) 7.55 (d, 1 H) 7.91 (d, 1 H) 7.92 (s, 1 H) 9.56 (s, 1 H). MS(10): 316.3-318.2 [M-1 ]
The synthetic route of 445-02-3 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; NOVARTIS AG; COOKE, Nigel Graham; FERNANDES GOMES DOS SANTOS, Paulo Antonio; FURET, Pascal; HEBACH, Christina; HOeGENAUER, Klemens; HOLLINGWORTH, Gregory; KALIS, Christoph; LEWIS, Ian; SMITH, Alexander Baxter; SOLDERMANN, Nicolas; STAUFFER, Frederic; STRANG, Ross; STOWASSER, Frank; TUFILLI, Nicola; VON MATT, Anette; WOLF, Romain; ZECRI, Frederic; WO2013/88404; (2013); A1;,
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