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With sodium carbonate; triphenylphosphine;palladium diacetate; In propan-1-ol; water; toluene; at 80℃;
l-[4-Ainino-7-bromo-2-(ethoxymethyl)-lH-imidazo[4,5-c][l,5]naphthyridin-l-yl]- 2-methylpropan-2-ol (0.039 g, 0.10 mmol) was added to a test tube. The boronic acid (0.11 mmol) indicated in the table below and n-propanol (1.6 niL) were sequentially added. The test tube was purged with nitrogen. Palladium (II) acetate (0.150 mL of a 4 rng/mL solution in toluene, 0.0026 mmol), 2 M aqueous sodium carbonate solution (0.600 rnL), deionized water (113 muL), and a solution of 0.15 mol% triphenylphosphine in n- propanol (53 muL, 0.0078 mmol) were sequentially added. The test tube was purged with nitrogen, capped, and then heated at 80 0C overnight.The contents of each test tube were passed through a Waters Oasis Sample Extractions Cartridge MCX (6 cc) according to the procedure described in Examples 4 - 58. The resulting basic solutions were concentrated by vacuum centrifugation. Each sample was subjected to the reaction with boron tribromide described in Examples 128 - 151 using 0.400 mL of boron tribromide solution for each test tube. Each reaction was stirred for six hours at room temperature. After methanol and 6 Nu hydrochloric acid were added to each tube, the contents were vortexed for 30 minutes, and the volatiles were removed by vacuum centrifugation. The compounds were purified by reversed phase prep HPLC according to the method described in Examples 77 - 127. The table below shows the reagent added to each test tube, the structure of the resulting compound, and the observed accurate mass for the isolated trifluoroacetate salt.
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