Hydrochloric Acid → HCID 178508370, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of {7-[bis(tert-butoxycarbonyl)amino]-4-[1-(trans-4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-1H-pyrazol-4-yl]furo[2,3-c]pyridin-2-yl}boronic acid (15.0, 0.0228 mmol), iodobenzene (9.32 mg, 0.0456 mmol), Pd(PPh3)4 (2.64 mg, 0.0023 mmol), potassium carbonate (9.47 mg, 0.0685 mmol) and 4:1 1,4-dioxane:water (1 mL) was heated to 65° C. for 30 min. Concentrated HCl (0.0381 mL, 0.457 mmol) was added, and the solution was heated to 70° C. for 1 h. The solution was concentrated. Purification by ISCO chromatography (2 to 5% 7 N NH3/MeOH:DCM) afforded 2.6 mg (30%) of the title compound as a yellow solid. 1H NMR (400 MHz, CD3OD): δ 1.43-1.58 (m, 2 H), 1.91-2.07 (m, 2 H), 2.07-2.24 (m, 4 H), 3.70 (tt, J=10.9, 4.3 Hz, 1 H), 4.21-4.32 (m, 1 H), 7.45-7.57 (m, 3 H), 7.58 (s, 1 H), 7.82 (s, 1 H), 7.92 (s, 1 H), 8.07 (s, 1 H), 8.09 (d, J=1.5 Hz, 1 H), 8.17 (s, 1 H); MS (ESI): 375.16 [M+H]+; HPLC tR=0.75 min (TOF: polar—2 min).

Provenance & Evidence