Preparation method of [1, 2, 4] oxadiazino indoline-3-ketone derivative

[0029] Example 1

[0030] Preparation of product 1:

[0031]

[0032] 0.20 mmol 2- (phenyl) nitrobenzene, 0.01 mmol trichloride was added to a reaction tube containing 0.50 ml of toluene, and at room temperature for 3 h, then 0.50 mmol N- (benzyloxy) -2 - bromine-2-methylpropamide, 1.0 mmol sodium carbonate, 1.0 mL hexafluoropropyl alcohol, room temperature reaction for 12 h. The reaction solution was extracted with water / dichloromethane (25 mL / 25 mL), and the organic phase concentrated was collected, and the column chromatography was purified to 67.3 mg of the target product, the yield was 81%, the structure of the compound as follows: 1 H NMR (400MHz, CDCL 3 Δ7.77 (D, J = 8.1 Hz, 1H), 7.65 (T, J = 7.7 Hz., 1H), 7.52-7.44 (M, 4H), 7.40-7.28 (M, 7H), 7.11 (T, J = 7.5 Hz, 1H), 5.01 (D, J = 8.8 Hz, 1H), 4.86 (D, J = 8.8 Hz, 1H), 1.59 (D, J = 4.4 Hz, 6H). 13 C NMR (100MHz, CDCL 3 Δ189.7, 168.9, 158.6, 137.6, 133.9, 133.8, 129.9, 129.4, 128.8, 128.6, 128.3, 127.7, 125.4, 122.8,

[0033] Example 2

[0034] Preparation of product 1:

[0035] 0.10 mmol 2- (phenylethynyl) nitrobenzene, 0.01 mmol of palladium, 0.10 mmol N- (benzyloxy) -2-bromo-2-methylpropamide, 0.20 mmol sodium carbonate, added to a contained 2.0 In the reaction tube of ML hexafluoropropyl alcohol, it was reacted at 60 ° C for 12 h, and the reaction liquid was extracted with water / dichloromethane (25 ml / 25 mL), and the organic phase concentration was collected, and the column chromatography was purified, and the yield of 45% was obtained. Target product (structures are characterized in Example 1).

[0036] Example 3

[0037] Preparation of product 1:

[0038] 0.10 mmol 2- (phenylene) nitrobenzene, 0.01 mmol of palladium, 0.10 mmol N- (benzyloxy) -2-bromo-2-methylpropamide, 0.20 mmol sodium carbonate, added to 2.0 ml of six In the reaction tube of fluoropropyl alcohol, at 60 ° C for 12 h, the reaction liquid was extracted with water / dichloromethane (25 ml / 25 mL), and the organic phase concentrated was collected. After the column chromatography was purified, the target product was obtained at 41% yield. (Structure Characterization Example 1).