1-(2,6-Dichlorophenyl)ethanol → 3-Bromo-7-[1-(2,6-dichlorophenyl)ethoxy]furo[3,2-c]pyridin-6-ylamine

Participants

Reaction Steps

3-Bromo-6-nitrofuro[3,2-c]pyridin-7-ol (Intermediate 10) was reacted with racemic 1-(2,6-dichlorophenyl)ethanol following the procedure described for Intermediate 8. The resulting 3-Bromo-7-[1-(2,6-dichlorophenyl)ethoxy]-6-nitrofuro[3,2-c]pyridine was reacted with iron/HCl as described in Example 2 to give 3-Bromo-7-[1-(2,6-dichlorophenyl)ethoxy]furo[3,2-c]pyridin-6-ylamine. Suzuki coupling with 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyrazol-1-yl]piperidine-1-carboxylic acid tert-butyl ester and Boc removal with HCl as described for Example 333 gave the title compound as HCl salt. 1H NMR (400 MHz, CD3OD): δ=1.86 (d, J=6.8 Hz, 3H), 1.91-2.03 (m, 2H), 2.11 (dd, J=12.0, 2.2 Hz, 2H), 2.75 (td, J=12.8, 2.5 Hz, 2H), 3.13-3.23 (m, 2H), 4.26-4.39 (m, 1H), 6.59 (q, J=6.8 Hz, 1H), 7.23 (d, J=7.8 Hz, 1H), 7.31-7.39 (m, 2H), 7.77 (s, 1H), 7.82 (s, 1H), 8.07 (s, 1H), 8.13 (s, 1H). MS (ES+): m/z 472.00/474.00 [MH+]. HPLC: tR=2.38 min (ZQ3, polar—5 min).

Provenance & Evidence