1,4-Dioxane → HCID 67064689, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of N-(7-chloropyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide (2D, 50 mg, 150 mmol), 3-Benzyloxyphenylboronic Acid (70 mg, 302 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (9 mg, 12 μmol) in 2:1 1,4-dioxane/saturated aqueous NaHCO3 (670 microliters of 1,4-dioxane and 0.5 microliters of saturated aqueous NaHCO3) was prepared in a 10 mL microwave reaction vessel and the sealed reaction vessel warmed to 110° C. for 20 minutes. The reaction mixture was cooled to rt, diluted with methanol, filtered, and purified via preparative HPLC, 60-80% (MeCN/H2O gradient+0.01% TFA). Lyophilization of the combined fractions gave the titled compound as a yellow solid (9.7 mg, 13%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.46 (s, 6 H) 5.21 (s, 2 H) 6.59 (d, J=2.27 Hz, 1 H) 7.27-7.32 (m, 1 H) 7.36 (d, J=7.33 Hz, 1 H) 7.39-7.44 (m, 1 H) 7.49-7.54 (m, 2 H) 7.49-7.57 (m, 1 H) 7.54-7.59 (m, 1 H) 7.60-7.67 (m, 3 H) 7.75-7.79 (m, 1 H) 8.01-8.06 (m, 3 H) 8.19 (d, J=2.27 Hz, 1 H) 11.26 (s, 1 H). ESI-MS: m/z 479.4 (M+H)+.

Provenance & Evidence