2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → 1-(4-(6-(3-Aminopyrrolidin-1-yl)pyridin-3-ylamino)-6-(3,5-dichloro-4-hydroxyphenyl)quinolin-3-yl)propan-1-one

Participants

Reaction Steps

Following general procedure D, tert-butyl 1-(5-(6-bromo-3-propionylquinolin-4-ylamino)pyridin-2-yl)pyrrolidin-3-ylcarbamate (100 mg, 0.18 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 (8 mg, 9% over two steps) as an orange-brown solid: 1H NMR (500 MHz, CD3OD+TFA-d) δ 9.29 (s, 1H), 8.27-8.19 (m, 2H), 8.07-7.99 (m, 2H), 7.85-7.70 (m, 1H), 7.29 (s, 2H), 6.96 (d, J=9.2 Hz, 1H), 4.15-4.05 (m, 1H), 4.07-3.99 (m, 1H), 3.89-3.80 (m, 1H), 3.79-165 (m, 2H), 3.27-3.18 (m, 2H), 2.63-2.52 (m, 1H), 2.34-2.23 (m, 1H), 1.31-1.22 (m, 3H); ESI MS m/z 522 [C27H25Cl2N5O2+H]+; HPLC 95.7% (AUC), tR=10.98 min.

Provenance & Evidence