2-Chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → HCID 66715296, compound

Participants

Reaction Steps

Following general procedure D, tert-butyl 1-(5-(6-bromo-3-(cyclopropanecarbonyl)quinolin-4-ylamino)pyrimidin-2-yl)pyrrolidin-3-ylcarbamate (100 mg, 0.18 mmol) was reacted with 2-chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (74 mg, 0.27 mmol) to obtain the protected intermediate which was subjected to general procedure A-2 to afford the desired product (42 mg, 45% over 2 steps) as a yellow-orange solid: 1H NMR (500 MHz, CD3OD+TFA-d) δ 9.35 (s, 1H), 8.48 (s, 2H), 8.25 (dd, J=8.8, 1.9 Hz, 1H), 8.19 (s, 1H), 8.04 (d, J=8.8 Hz, 1H), 7.22 (s, 2H), 4.06 (m, 2H), 3.91 (dt, J=11.7, 7.4 Hz, 1H), 3.82 (m, 2H), 2.82 (s, 1H), 2.54 (td, J=13.1, 6.8 Hz, 1H), 2.24 (td, J=13.2, 5.7 Hz, 1H), 1.21 (s, 4H); ESI MS m/z 519 [C27H24ClFN6O2+H]+; HPLC 99.7% (AUC), tR=10.05 min.

Provenance & Evidence