2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → HCID 66715669, 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 2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (112 mg, 0.39 mmol) to obtain the protected intermediate which was subjected to general procedure A-2 to afford the desired product (8.0 mg, 8% over 2 steps) as a yellow solid. 1H NMR (500 MHz, MeOD+TFA-d) δ 9.33 (br s, 1H), 8.44 (s, 2H), 8.27 (dd, J=8.9, 1.8 Hz, 1H), 8.29-8.19 (m, 1H), 8.04 (d, J=8.9 Hz, 1H), 7.44 (br s, 2H), 4.81-4.71 (m, 1H), 4.48-4.44 (m, 1H), 3.46-3.31 (m, 3H), 2.84-2.77 (m, 1H), 2.23-2.16 (m, 1H), 1.96-1.87 (m, 1H), 1.80-1.60 (m, 2H), 1.21-1.15 (m, 4H); ESI MS m/z 549 [C28H26Cl2N6O2+H]+; HPLC>99% (AUC), tR=11.00 min.

Provenance & Evidence