2-ETHOXYPYRIMIDINE-5-BORONICACID

To a solution of 8-bromo-9-(4-{[(3S)-1-(3-fluoropropyl)pyrrolidin-3-yl]oxy}phenyl)-6, 7-dihydro-5H-benzo[7]annulen-3-ol (D4) (74.9 mg, 162.69 mumol), in dioxane (1 ml) and water (0.5 ml), was added A mixture of intermediate 17.7 (1 .63g), To a glass vial was added 2-methoxypyrimidine-5-boronic acid (0.105 g, 0.613 mmol), (2- chloropyrimidin-4-yl)-(l-isopropyl-lH-imidazo[4, 5-c]pyridin-6-yl)amine (Example 12, Step 4) (0.176 mg, 0.613 mmol), Pd(Amphos)2Cl2 (22 mg, 0.031 mmol), a 2M solution of Na2C03 (0.46 mL, 0.92 mmol) and acetonitnle (2.5 mL). The mixture was degassed by nitrogen bubbling for 20 min. The reaction vial was sealed and heated in a microwave at 140 C for 20 min. Alternatively, the reaction was sealed and stirred at 100 C in an oil bath for 2 h. The reaction mixture was cooled to room temperature, filtered and concentrated. The crude product was purified by reverse- phase HPLC and lyophilized to give the title compound (41 mg, 18%). LCMS (ESI): RT 3.91 min, [M+H]+ 377.2, method = B; lH NMR (400 MHz, DMSO-d6) delta 10.31 (s, 1H), 9.40 (s, 2H), 8.73 (d, J= 1.0 Hz, 1H), 8.46 (d, J= 5.9 Hz, 1H), 8.39 (d, J= 7.9 Hz, 2H), 7.30 (s, 1H), 4.85 - 4.71 (m, 1H), 4.46 (q, J= 7.1 Hz, 2H), 1.61 (d, J= 6.8 Hz, 6H), 1.38 (t, J= 7.1 Hz, 3H).Example 343 4-(2-Ethoxy-pyrimidin-5-yl)-2-(2-quinolin-2-yl-ethyl)-2, 3-dihydro-isoindol-1-one The title compound was prepared in analogy to the process described in Example 341 but using Example 327 4-(2-Ethoxy-pyrimidin-5-yl)-6-(2-quinolin-2-yl-ethyl)-6, 7-dihydro-pyrrolo[3, 4-b]pyridin-5-one The title compound was prepared in analogy to the process described in Example 322 but using

Molecular Weight:167.96
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:3
Exact Mass:168.0706223
Monoisotopic Mass:168.0706223
Topological Polar Surface Area:75.5
Heavy Atom Count:12
Complexity:128
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes