Application of Ethyl 6-bromobenzo[d]isoxazole-3-carboxylate

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The naphthyridine compound, cas is 55716-28-4 name is 8-Methoxy-1,7-naphthyridin-6-amine, mainly used in chemical industry, its synthesis route is as follows.

55716-28-4, EXAMPLE 76; N-(2-Chloro-5-(8-methoxy-l,7-naphthyridin-6-yl)pyridin-3-yl)-4- fluorobenzenesulfonamide; (1) 8-methoxy-l,7-naphthyridin-6-yl trifluoromethanesulfonate.; (Some starting materials may be obtained from Parkway Scientific, NY, NY) To a 50 mL round- bottomed flask was added 8-methoxy-l,7-naphthyridin-6-amine (175 mg, 999 mumol), DMF (1.6 mL), trifluoromethane sulfonic acid (0.8 mL, 9041 mumol), sodium nitrite (0.06 mL, 1998 mumol). The reaction mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with water (10 mL) and extracted with EtOAc (2 x 40 mL). The organic extract was washed with water (10 mL), satd NaCl (10 mL), dried over Na2SO4, filtered and concentrated in vacuo and the residue was purified by silica gel chromatography, eluting with 60% EtOAc/hexanes to give 8-methoxy-l,7-naphthyridin-6-yl trifluoromethanesulfonate (126mg, 41% yield). MS (ESI pos. ion) m/z calc’d for Ci0H7F3N2O4S: 308.0; found 309.0. 1H NMR (300 MHz, CHLOROFORM-^) delta ppm 4.25 (s, 3 H) 7.13 (s, 1 H) 7.70 (dd, J=8.33, 4.24 Hz, 1 H) 8.19 (dd, J=8.40, 1.53 Hz, 1 H) 9.04 (dd, J=4.24, 1.61 Hz, 1 H)

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Reference£º
Patent; AMGEN INC.; WO2009/155121; (2009); A2;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem