2-Chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → HCID 66715518, compound

Participants

Reaction Steps

Following general procedure D, tert-butyl 1-(5-(6-bromo-3-(cyclopropanecarbonyl)quinoline-4-ylamino)pyrimidin-2-yl)piperidin-3-ylcarbamate (150 mg, 0.26 mmol) was reacted with 2-chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (106 mg, 0.39 mmol) to obtain the protected intermediate which was subjected to general procedure A-2 to afford the desired product (28 mg, 23% over 2 steps) as a yellow solid. 1H NMR (500 MHz, MeOD+TFA-d) δ 9.34 (br s, 1H), 8.45 (s, 2H), 8.25 (dd, J=8.8, 1.9 Hz, 1H), 8.21 (br s, 1H), 8.04 (d, J=8.8 Hz, 1H), 7.25 (br s, 1H), 4.81-4.74 (m, 1H), 4.47 (d, J=12.8 Hz, 1H), 3.48-3.31 (m, 3H), 2.80 (br s, 1H), 2.24-2.16 (m, 1H), 1.97-1.87 (m, 1H), 1.81-1.62 (m, 2H), 1.21-1.16 (m, J=7.3 Hz, 4H); ESI MS m/z 533 [C28H26ClFN6O2+H]+; HPLC>99.0% (AUC), tR=10.89 min.

Provenance & Evidence