2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → HCID 66715650, compound

Participants

Reaction Steps

Following general procedure D, tert-butyl 2-(5-(6-bromo-3-(cyclopropanecarbonyl)quinolin-4-ylamino)pyridin-2-yloxy)ethylcarbamate (100 mg, 0.19 mmol) was reacted with 2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (81 mg, 0.28 mmol) to obtain the protected intermediate which was subjected to general procedure A-2 to afford the desired product (21 mg, 22% over two steps) as a yellow solid: 1H NMR (500 MHz, CD3OD+TFA-d) δ 9.40 (s, 1H), 8.33-8.24 (m, 2H), 8.13-8.04 (m, 2H), 7.83 (dd, J=8.8, 2.8 Hz, 1H), 7.37 (s, 2H), 7.14 (d, J=8.8 Hz, 1H), 4.66 (t, J=5.1 Hz, 2H), 3.43 (t, J=5.1 Hz, 2H), 2.87-2.80 (m, 1H), 1.22-1.15 (m, 4H); ESI MS m/z 509 [C26H22Cl2N4O3+H]+; HPLC 99.7% (AUC), tR=11.26 min.

Provenance & Evidence