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. 2020 Jul 28;63(17):9300–9315. doi: 10.1021/acs.jmedchem.0c00451

Scheme 2. Synthesis of 4-(2-(5-(Aminomethyl)-2-methoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)-2-isopropylbenzoic Acid 12.

Scheme 2

Reagents and conditions: (i) 4-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile, Pd(PPh3)4, Na2CO3, 1,4-dioxane, 110 °C, 18 h; (ii) CH3OH, K2CO3, 55 °C, 18 h; (iii) 2-isopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid, Pd(dppf)Cl2.CH2Cl2, Na2CO3, 1,4-dioxane, 110 °C, 0.5 h, MW; and (iv) CoCl2·6H2O, NaBH4, CH3OH.