Hydrochloric Acid → HCID 86687703, compound

Participants

Reaction Conditions

Reaction Steps

A microwave vial charged with di-tert-butyl(2′,4′,6′-triisopropyl-3,4,5,6-tetramethyl-[1,1′-biphenyl]-2-yl)phosphine (0.034 g, 0.070 mmol), 3-fluorophenol (0.079 g, 0.703 mmol), 1-(4-chloro-2-methoxyphenyl)-N-(pyrimidin-4-yl)isoquinoline-6-sulfonamide (0.150 g, 0.351 mmol), potassium phosphate (0.298 g, 1.406 mmol), and 1.5 mL dioxane was heated to 165° C. in the microwave for 30 minutes. LC/MS showed product, so the reaction mixture was filtered through a 0.45 μm syringe filter and was treated with HCl (4N in dioxane) (0.351 ml, 1.406 mmol). After stirring for 10 minutes, the reaction mixture was concentrated. Purification of the crude residue by reverse phase column chromatography [RediSep Gold C18, 10-100% (0.1% NH4OH in MeOH)/(0.1% NH4OH in water)] gave 1-(4-(3-fluorophenoxy)-2-methoxyphenyl)-N-(pyrimidin-4-yl)isoquinoline-6-sulfonamide (0.015 g, 0.030 mmol, 8.49% yield). 1H NMR (MeCN-d3) δ: 8.69 (d, J=5.7 Hz, 1H), 8.62 (s, 1H), 8.48 (s, 1H), 8.22 (d, J=6.3 Hz, 1H), 7.89-7.97 (m, 2H), 7.80-7.88 (m, 1H), 7.38-7.47 (m, 1H), 7.35 (d, J=8.2 Hz, 1H), 7.08 (d, J=5.9 Hz, 1H), 6.87-6.99 (m, 4H), 6.76 (d, J=8.3 Hz, 1H), 3.59-3.62 (m, 3H); (M+H)+=503.0.

Provenance & Evidence