Reaction SMILES: COCC1NC2C=C([NH:13][C:14]3[N:29]=[C:17]4[CH:18]=[CH:19][CH:20]=[C:21]([CH2:22][CH:23]5[CH2:28][CH2:27][O:26][CH2:25][CH2:24]5)[N:16]4[N:15]=3)C=CC=2N=1.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.[CH3:72][O:73][CH2:74][C:75]1[N:79](S(C2C=CC(C)=CC=2)(=O)=O)[C:78]2[CH:90]=[CH:91][C:92](N)=[CH:93][C:77]=2[N:76]=1.BrC1N=C2C=CC=C(CC3CCOCC3)N2N=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:72][O:73][CH2:74][C:75]1[NH:76][C:77]2[CH:93]=[C:92]([C:20]3[CH:19]=[CH:18][C:17]4[N:16]([N:15]=[C:14]([NH2:13])[N:29]=4)[C:21]=3[CH2:22][CH:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)[CH:91]=[CH:90][C:78]=2[N:79]=1
Reactant: COCc1nc2ccc(Nc3nc4cccc(CC5CCOCC5)n4n3)cc2[nH]1
Reactant: COCc1nc2cc(N)ccc2n1S(=O)(=O)c1ccc(C)cc1
Agent: [Pd]
Agent: Brc1nc2cccc(CC3CCOCC3)n2n1
Agent: CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21
Solvent: C1COCCO1
Product: COCc1nc2ccc(-c3ccc4nc(N)nn4c3CC3CCOCC3)cc2[nH]1
Temperature: 120 °C
Reaction time: 3 h

Procedure:
N-(2-(methoxymethyl)-1H-benzo[d]imidazol-6-yl)-5-((tetrahydro-2H-pyran-4-yl)methyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine. To a mixture of tris(dibenzylideneacetone)dipalladium(0) (0.077 g, 0.084 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.098 g, 0.169 mmol) in 1,4-dioxane (10 mL) was added 2-(methoxymethyl)-1-tosyl-1H-benzo[d]imidazol-5-amine (0.280 g, 0.844 mmol), 2-bromo-5-((tetrahydro-2H-pyran-4-yl)methyl)-[1,2,4]triazolo[1,5-a]pyridine (0.25 g, 0.844 mmol) and finely ground potassium carbonate (0.35 g, 2.53 mmol) in a sealable vessel with a stir bar. Nitrogen was blown in to blow out air. The resulting mixture was sealed, stirred, and heated at 120° C. LCMS after 3 h shows complete conversion to desired product. The resulting mixture was filtered. Saturated aqueous sodium bicarbonate was added and extracted with ethyl acetate (2×100 mL). The combined organics were dried over magnesium sulfate, filtered, and concentrated on a rotary evaporator to dryness and purified using reverse-phase preparatory HPLC (eluting with 20-70% acetonitrile+0.1% trifluoroacetic acid in water+0.1% trifluoroacetic acid, over 39 min). Fractions containing the desired product were concentrated on a rotary evaporator and aqueous hydrochloric acid (25 mL, 6M) was added and heated to 70° C. overnight. The solvent was removed on a rotary evaporator and purified using reverse-phase semi-preparatory HPLC (eluting with 5-40% acetonitrile+0.1% trifluoroacetic acid in water+0.1% trifluoroacetic acid, over 39 min). Fractions containing the desired product were loaded onto a Strata X—C ion exchange column from Phenomenex. The column was washed successively with water, acetonitrile, methanol, and then hot 10% ammonium hydroxide in methanol. The product eluted with the 10% ammonium hydroxide in methanol and was concentrated on a rotary evaporator to dryness. This material was crystallized from 20% ethyl acetate in hexane and dried under high vacuum at 40° C. to give the desired product as a white solid (0.130 g, 0.331 mmol, 39.2% yield). 1H NMR (400 MHz, DMSO-d6) δ (ppm) 12.30 (br s, 1H), 9.56 (br s, 1H), 8.14 (s, 1H), 7.30-7.55 (m, 4H), 6.89 (d, J=5.86 Hz, 1H), 4.58 (s, 2H), 3.84 (dd, J=11.32, 2.73 Hz, 2H), 3.36 (s, 3H), 3.26 (t, J=10.93 Hz, 2H), 3.06 (d, J=7.03 Hz, 2H), 2.19-2.36 (m, 1H), 1.54 (d, J=11.32 Hz, 2H), 1.29-1.45 (m, 2H); MS (ESI) m/z 393.2 [M+1]+.