Phenylboronic Acid → HCID 67064835, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of N-(7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(1-hydroxy-2-methylpropan-2-yl)benzamide (4G, 44 mg, 1.0 equivalent), phenylboronic acid (1.5 equivalents) and [1,1′-bis(diphenylphosphino)ferrocene] dichloropalladium(II) (0.09 equivalents) in 2:1 dioxane/saturated aqueous NaHCO3 (0.125 M with respect to 4G) was warmed to 110° C. in a microwave reactor. The reaction mixture was cooled to room temperature, diluted with methanol, filtered, and purified via preparative HPLC to afford the title compound (49%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.26 (s, 6 H), 2.40 (s, 3 H), 3.47 (s, 2 H), 4.76 (br. s., 1 H), 6.40 (s, 1 H), 7.53 (d, J=8.59 Hz, 2 H), 7.58-7.68 (m, 3 H), 7.94-8.04 (m, 3 H), 8.04-8.10 (m, 2 H), 11.19 (s, 1 H). ESI-MS: m/z 401.1 (M+H)+.

Provenance & Evidence