Reaction SMILES: CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:43][O:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[C:51]1[C:52]2[N:53]([N:57]=[C:58]([NH2:60])[N:59]=2)[CH:54]=[CH:55][CH:56]=1.Br[C:62]1[CH:67]=[CH:66][C:65]([N:68]2[CH2:73][CH2:72][O:71][CH2:70][CH2:69]2)=[CH:64][CH:63]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O1CCOCC1>[CH3:43][O:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[C:51]1[C:52]2[N:53]([N:57]=[C:58]([NH:60][C:62]3[CH:63]=[CH:64][C:65]([N:68]4[CH2:69][CH2:70][O:71][CH2:72][CH2:73]4)=[CH:66][CH:67]=3)[N:59]=2)[CH:54]=[CH:55][CH:56]=1
Reactant: COc1ccccc1-c1cccn2nc(N)nc12
Reactant: Brc1ccc(N2CCOCC2)cc1
Agent: [Pd+2]
Agent: CC(=O)[O-]
Agent: CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21
Solvent: C1COCCO1
Product: COc1ccccc1-c1cccn2nc(Nc3ccc(N4CCOCC4)cc3)nc12
Temperature: 80 °C

Procedure:
To a solution of 3-bromo-pyridin-2-ylamine (9.72 g, 56.2 mmol) in 1,4-dioxane (100 mL) was added dropwise ethoxycarbonyl isothiocyanate (6.70 mL, 56.7 mmol). The mixture was stirred under an atmosphere of nitrogen for 18 hours. The volatiles were evaporated to yield a waxy solid. The recovered material was triturated with hexane (250 mL). N-(3-Bromo-2-pyridinyl)-N′-carboethoxy-thiourea was isolated and was used without further purification. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 11.46 (s, 1H), 11.43 (s, 1H), 8.49 (dd, J=4.6, 1.5 Hz, 1H), 8.18 (dd, J=8.0, 1.5 Hz, 1H), 7.33 (dd, J=8.0, 4.7 Hz, 1H), 4.23 (q, J=7.1 Hz, 2H), 1.27 (t, J=7.2 Hz, 3H). MS=215 (MH)+. 2b) To a stirred suspension of hydroxylamine hydrochloride (17.4 g, 25.0 mmol) and N,N-diisopropylethylamine (26.0 mL, 14.9 mmol) in a mixture of methanol (70 mL) and ethanol (70 mL) was added N-(3-bromo-2-pyridinyl)-N′-carboethoxy-thiourea. The mixture was stirred for 2 hours at room temperature then heated to 60° C. for 18 hours. The suspension was cooled to room temperature, filtered and rinsed with methanol, water then methanol. 8-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine was isolated as an off-white solid (8.41 g, 70%). 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 8.58 (d, J=6.4 Hz, 1H), 7.73 (d, J=7.6 Hz, 1H), 6.80 (t, J=7.0 Hz, 1H), 6.25 (s, 2H). MS=213, 215 (MH)+. 2c) An oven dried tube was charged with palladium acetate (0.20 g, 0.89 mmol) and triphenylphosphine (0.60 g, 2.3 mmol). The tube was evacuated under high vacuum and backflushed under a stream of nitrogen for 5 minutes. 1,4-Dioxane (10 mL) was added and the mixture was stirred under nitrogen for 10 minutes. 8-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (1.0 g, 4.7 mmol), 2-methoxybenzeneboronic acid (1.1 g, 7.0 mmol), N,N-dimethylformamide (10 mL) and 1.50 M of sodium carbonate in water (10 mL) were added. The mixture was stirred for 2 minutes at room temperature under nitrogen then the tube was sealed and heated at 80° C. for 18 hours. The mixture was transferred to a round bottom flask and the volatiles were evaporated under reduced pressure. Water (100 mL) was added and the mixture was stirred when a precipitate was formed. The solid was collected by filtration, rinsed with water, air dried, triturated with ether/dichloromethane (4:1; 10 mL), filtered and rinsed with ether. 8-(2-Methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine was isolated (1.0 g, 89%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.50 (d, J=6.5 Hz, 1H), 7.51 (dd, J=7.6, 1.5 Hz, 1H), 7.43-7.36 (m, 2H), 7.13 (d, J=8.1 Hz, 1H), 7.02 (t, J=7.3 Hz, 1H), 6.91 (t, J=7.0 Hz, 1H), 5.96 (br s, 2H), 3.73 (s, 3H). MS=241 (MH)+. 2d) To an oven dried tube was added palladium acetate (10.0 mg, 0.0445 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (75.0 mg, 0.130 mmol), 8-(2-methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (100.0 mg, 0.4162 mmol), 4-(4-bromo-phenyl)-morpholine (120.0 mg, 0.4956 mmol), cesium carbonate (270 mg, 0.83 mmol) and 1,4-dioxane (5 mL). The tube was evacuated and backflushed with nitrogen three times. The tube was sealed and heated at 80° C. for 72 hours. The mixture was cooled to room temperature, diluted with dichloromethane (10 mL), filtered through a plug of diatomaceous earth, rinsed with dichloromethane and evaporated. The material was purified via chromatography utilizing an ISCO automated purification apparatus (amine modified silica gel column 5%→100% ethyl acetate in hexanes). The title compound, [8-(2-Methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(4-morpholin-4-yl-phenyl)-amine, was isolated as a pale yellow foam (0.034 g, 20%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.39 (dd, J=6.7, 1.1 Hz, 1H), 7.61 (dd, J=7.5, 1.7 Hz, 1H), 7.51 (dd, J=7.3, 0.9 Hz, 1H), 7.50-7.45 (m, 2H), 7.43-7.37 (m, 1H), 7.12-7.07 (m, 1H), 7.05 (d, J=8.2, 1H), 6.96-6.87 (m, 3H), 6.67 (s, 1H), 3.89-3.85 (m, 4H), 3.81 (s, 3H), 3.12-3.08 (m, 4H). MS=402 (MH)+.