2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → HCID 66715461, compound

Participants

Reaction Steps

Following general procedure D, tert-butyl 3-(5-(6-bromo-3-(cyclopropanecarbonyl)quinoline-4-ylamino)pyridin-2-ylamino)pyrrolidine-1-carboxylate (100 mg, 0.18 mmol) was reacted with 2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (78 mg, 0.27 mmol) to obtain the protected intermediate which was subjected to general procedure A-2 to afford the desired product (43 mg, 45% over 2 steps) as a yellow-orange solid: 1H NMR (500 MHz, MeOD+TFA-d) δ 9.40 (br s, 1H), 8.26-8.07 (m, 3H), 8.00 (d, J=8.9 Hz, 1H), 7.57 (dd, J=8.9, 2.7 Hz, 1H), 7.34 (s, 2H), 6.85-6.77 (m, 1H), 4.65-4.56 (m, 1H), 3.66-3.49 (m, 2H), 3.44-3.30 (m, 2H), 2.86 (br s, 1H), 2.47-2.36 (m, 1H), 2.18-2.07 (m, 1H), 1.27-1.15 (m, 4H). ESI MS m/z 534 [C28H25Cl2N5O2+H]+; HPLC>99.0% (AUC), tR=10.64 min.

Provenance & Evidence