Trifluoroacetic acid → HCID 54671063, compound

Participants

Reaction Conditions

Reaction Steps

6-Fluoro-7-iodo-1-(2-methoxyethyl)-1H-pyrazolo[4,3-b]pyridine (45 mg, 0.140 mmol) were combined in dioxane (4 mL) and the following was added sequentially (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (20.27 mg, 0.035 mmol), Tris(dibenzylideneacetone)dipalladium(0) (32.1 mg, 0.035 mmol), sodium tert-butoxide (40.4 mg, 0.420 mmol) and 2-(5-chloro-2-fluorophenyl)-5-methylpyridin-4-amine (7) (33.2 mg, 0.140 mmol). The reaction vessel was sealed and heated at 110° C. for an hour. The mixture was then cooled, evaporated to dryness, the residue was dissolved in DMF and purified by preparative HPLC (eluting with gradient of 20-45% ACN (containing 0.035% TFA) in water (containing 0.05% TFA) using a Sunfire Prep 5 μm C18, 75×30 mm column) to give the title compound (30 mg, 49.8% yield) as a TFA salt. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.44 (s, 3H) 3.12 (s, 3H) 3.59-3.81 (m, 2H) 4.57 (t, J=5.18 Hz, 2H) 7.09 (s, 1H) 7.42 (dd, J=10.11, 9.09 Hz, 1H) 7.55-7.70 (m, 1H) 7.77 (dd, J=6.44, 2.65 Hz, 1H) 8.53 (s, 1H) 8.67 (br. s., 1H) 8.80 (s, 1H) 9.70 (br. s., 1H). MS [M+H] found 430.3.

Provenance & Evidence