4-Bromo-1H-pyrrolo(2,3-c)pyridine → 4-(1-((7-morpholino-5-(1H-pyrrolo[2,3-c]pyridin-4-yl)thiazolo[5,4-d]pyrimidin-2-yl)methyl)azetidin-3-yl)morpholine

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A degassed solution of 7-morpholin-4-yl-2-(3-morpholin-4-yl-azetidin-1-ylmethyl)-5-(tributylstannanyl)thiazolo[5,4-d]pyrimidine (120 mg, 0.18 mmol), 4-bromo-1H-pyrrolo[2,3-c]pyridine (46 mg, 0.23 mmol), PdCl2{PtBu2(Ph-p-Nme2)}2 (13 mg, 0.018 mmol) and copper(I) thiophene-2-carboxylate (7 mg, 0.036 mmol) in 1,4-dioxane (2.5 mL) was subjected to microwave irradiation at 140° C. for 20 minutes. The reaction mixture was cooled to ambient temperature and loaded onto an Isolute® SCX-2 cartridge (10 g). The cartridge was then washed with MeOH and the desired product was subsequently eluted using 2 M NH3 in MeOH. The product was collected and concentrated to give a yellow oil. The oil was purified by chromatography (Si—PPC, DCM:MeOH, 100:0 to 98:2 to 95:5) to afford 168 as a yellow solid (12 mg, 14%). LCMS (Method E): RT=4.15 min, [M+H]− 493.2. 1H NMR (CDCl3, 400 MHz) δ 9.28 (bs, 1 H), 8.90 (s, 1 H), 7.53 (m, 2 H), 4.45 (m, 4 H), 4.02 (s, 2H), 3.90 (t, J=4.7 Hz, 4 H), 3.76-3.65 (m, 6 H), 3.19-3.09 (m, 3 H), 2.36 (d, J=4.76 Hz, 4H).

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