Compound 5

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

7-(3-((3-Formyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)methyl)-1,5-di methyl-1H-pyrazol-4-yl)-3-(3-(naphthalen-1-yloxy)propyl)-1H-indole-2-carboxylic acid 19 (20 mg, 0.028 mmol) was dissolved in acetonitrile (5 mL) and 1N aq HCl (5 mL) was added followed by polymer supported boronic acid (40 mg, Sigma-Aldrich, Catalog No 632627-1G). The reaction was stirred at room temperature overnight, filtered and concentrated. The crude product was purified by reverse-phase chromatography using 50 to 70% acetonitrile in H₂O with 0.1% TFA, affording pure product 5 as an off-white powder (10 mg, 58% yield). Spectral data: ¹H NMR (300 MHz, CDCl₃) δ ppm 2.19 (tt, J = 7.40, 6.47 Hz, 2H), 2.24 (s, 3H), 3.38 (t, J = 7.40 Hz, 2H), 3.81 (s, 3H), 4.22 (t, J = 6.47 Hz, 2H), 5.16 (s, 2H), 6.73 (d, J = 6.0 Hz, 1H), 7.07 (dd, J = 9.0, 3.0 Hz, 1H), 7.14 (s, 1H), 7.15 (s, 1H), 7.32-7.39 (dd, J = 8.0, 7.6 Hz, 1H), 7.40 - 7.42 (m, 2H), 7.43-7.48 (m, 2H), 7.49-7.52 (m, 2H), 7.68 (q, J = 3.0 Hz, 1H), 7.79-7.84 (m, 1H), 8.32-8.39 (m, 1H), 9.20 (s, 1H), 10.51 (s, 1H); ¹³C NMR (300 MHz, CDCl₃) 10.26, 21.86, 32.79, 36.81, 62.42, 66.91, 103.92, 104.23, 108.13, 114.30, 119.90, 120.04, 120.77, 121.07, 121.10, 121.67, 121.82, 123.12, 125.09, 125.38, 125.70, 126.57, 127.57, 127.78, 134.17, 134.34, 135.57, 136.28, 139.82, 145.91, 156.00, 156.76, 159.99, 161.42, 193.79; MS-ESI (m/z): [M + H]⁺ calcd for C₃₅H₃₂BN₃O₇, 618.25; found 618.2.

PubChemID:

316894742

MDL Molfile:

41589_2016_BFnchembio2174_MOESM9_ESM.mol

ChemDraw:

41589_2016_BFnchembio2174_MOESM10_ESM.cdx