2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → HCID 178458758, compound

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Reaction Steps

Following general procedure M, 1-(6-bromo-4-((trans-4-((dimethylamino)methyl)cyclohexyl)amino)quinolin-3-yl)propan-1-one (125 mg, 0.30 mmol) was reacted with 2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (95 mg, 0.33 mmol) to afford the desired product (53 mg, 35%) as a yellow solid. NMR (500 MHz, DMSO-d6) δ 10.50 (d, J=8.0 Hz, 1H), 8.96 (s, 1H), 8.31 (d, J=2.1 Hz, 1H), 8.04 (dd, J=8.7, 1.9 Hz, 1H), 7.85 (d, J=8.7 Hz, 1H), 7.72 (s, 2H), 4.14-4.06 (m, 1H), 3.13 (q, J=7.2 Hz, 2H), 2.23-2.15 (m, 2H), 2.18 (s, 6H), 2.15-2.10 (m, 1H), 1.88 (d, J=12.9 Hz, 2H), 1.61-1.43 (m, 3H), 1.17-1.01 (m, 5H). ESI MS m/z 500 [C27H31Cl2N3O2+H]+; HPLC>99% (AUC), tR=8.70 min.

Provenance & Evidence