| 72% |
|
Example 19A3-Bromo-1-(2-methoxy-4-nitrophenyl)pyridin-2(1H)-one 70 g (403 mmol) of 3-bromopyridin-2(1H)-one are dissolved in 1 l of anhydrous dimethyl sulphoxide, and 54 g (484 mmol) of potassium tert-butoxide are added at room temperature. The suspension is stirred at this temperature for 1 h. 69 g (403 mmol) of <strong>[454-16-0]1-fluoro-2-methoxy-4-nitrobenzene</strong> are added, and the reaction solution is heated at 80° C. for 20 h. Carefully, the mixture is diluted with 5 l of water. The precipitated solid is filtered off, washed with water and dried under reduced pressure. This gives 103 g (72percent of theory) of the desired product.1H-NMR (400 MHz, DMSO-d6, delta/ppm): delta=8.05 (dd, 1H), 8.1 (d, 1H), 7.95 (dd, 1H), 7.7 (d, 1H), 7.6 (dd, 1H), 6.3 (t, 1H), 3.9 (s, 3H).MS (ESIpos): m/z=342 (M+NH4)+ |
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With potassium tert-butylate; In water; dimethyl sulfoxide; |
Example 28A 3-Bromo-1-(2-methoxy-4-nitrophenyl)pyridin-2(1H)-one 70 g (403 mmol) of 3-bromopyridin-2(1H)-one are dissolved in 1 l of anhydrous dimethyl sulphoxide, and 54 g (484 mmol) of potassium tert-butoxide are added at room temperature. The suspension is stirred at this temperature for 1 h. 69 g (403 mmol) of <strong>[454-16-0]1-fluoro-2-methoxy-4-nitrobenzene</strong> are added, and the reaction solution is heated at 80° C. for 20 h. Carefully, the mixture is diluted with 5 l of water. The precipitated solid is filtered off, washed with water and dried under reduced pressure. This gives 103 g (72percent of theory) of the desired product. 1H-NMR (400 MHz, DMSO-d6, delta/ppm): delta=8.05 (dd, 1H), 8.1 (d, 1H), 7.95 (dd, 1H), 7.7 (d, 1H), 7.6 (dd, 1H), 6.3 (t, 1H), 3.9 (s, 3H). MS (ESIpos): m/z=342 (M-FNH4)+ |
| 38.7 g |
With potassium phosphate; In 1-methyl-pyrrolidin-2-one; at 120℃; for 6h; |
Example 5 Preparation of 3-bromo-1-(2-methoxy-4-nitrophenyl)pyridin-2(1H)-one 36.2 g of 3-bromopyridone (87percent purity, 0.18 mol) and 29.4 g of <strong>[454-16-0]<strong>[454-16-0]4-fluoro-3-methoxynitrobenze</strong>ne</strong> (0.17 mol) were introduced as initial charge in 180 ml of N-methylpyrrolidone; 46.1 g of anhydrous potassium phosphate (0.22 mol) were added and the reaction mixture was carried out at 120° C. for 6 h. After cooling to 90° C., water was added and the mixture was cooled to room temperature. The precipitate was filtered off, washed with water and stirred with a methanol/water mixture (1:1). The solid was filtered off, washed and dried in the air. This gave 38.7 g (66percent) of the desired target compound.[0098] HPLC (method 3): Rt=3.50 min. [0099] LC-MS (method 4): Rt=0.84 min. [0100] 1H NMR (400 MHz, DMSO-d6): delta [ppm]=3.91 (s, 3H), 6.30 (t, 1H), 7.64 (dd, 1H), 7.70 (d, 1H), 7.96 (dd, 1H), 8.00 (m, 1H), 8.04 (dd, 1H). [0101] MS (ES+): [M+H]+ 327 or 325. |
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