2-Formylphenylboronic acid → HCID 86604965, compound

Participants

Reaction Steps

A solution of methyl 2-bromo-3-cyclohexyl-1-(2,2-dimethoxyethyl)-1H-indole-6-carboxylate (0.16 M, 1 eq, from Step 1) in dioxane and Na2CO3 (6 eq of a 2M solution) was degassed by sonication for 10 min. 2-Formylphenylboronic acid (1.5 eq) and bis(triphenylphosphine) palladium(II)dichloride (20 mol %) were added and the reaction placed in a pre-heated oil bath at 108° C. for 20 min. After cooling to RT, the reaction was partitioned between H2O and EtOAc (×3). The combined organics were washed with HCl (1N), H2O, and brine before being dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash column chromatography (Biotage, 10% EtOAc/PE) gave the title compound as a pale yellow solid (85%); MS (ES+) m/z 472 (M+Na)+, 450 (M+H)+.

Provenance & Evidence