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

Scheme 3. Synthesis of 2-Isopropyl-4-(2-(2-methoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)benzoic Acid 15, 4-(2-(5-((Diethylamino)methyl)-2-hydroxyphenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)-2-isopropylbenzoic Acid 19, 4-(2-(3-((Diethylamino)methyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)-2-isopropylbenzoic Acid 23 and [4-(2-(3-((Diethylamino)methyl)-2-methoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)-2-isopropylbenzoic Acid] 27.

Scheme 3

Reagents and conditions: (i) (2-methoxyphenyl)boronic acid, Pd(PPh3)4, Na2CO3, 1,4-dioxane, 110 °C, 12 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; (iv) 4-(methoxymethoxy)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde or 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde, Pd(PPh3)4, Na2CO3, 1,4-dioxane, 110 °C, 18 h; (v) Et2NH, NaBH(AcO)3, 1,4-dioxane, rt, 18 h; and (vi) HCl, MeCN/H2O 3:1.