Potassium Phosphate, Tribasic → HCID 59375021, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-bromo-2-(hydroxymethyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide (Intermediate 30-3(a), 80 mg, 0.248 mmol), 2-(2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)isoindolin-1-one (Intermediate 50-4, 130 mg, 0.371 mmol), 2 M aqueous tripotassium phosphate (0.371 mL, 0.743 mmol), and tetrakis(triphenylphosphine)palladium (14.30 mg, 0.012 mmol) in toluene (3 mL) and ethanol (1 mL) was sealed in a vial and heated at 100° C. for 6 hrs. The mixture was cooled and diluted with EtOAc, and the solution was washed with water, dried and concentrated. The residue was purified by column chromatography (eluting with a gradient from DCM to 96:3.6:0.4 DCM-methanol-28% aqueous ammonium hydroxide) to provide 2-(hydroxymethyl)-5-(2-methyl-3-(1-oxoisoindolin-2-yl)phenyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide as a light yellow solid (68 mg, 53%). 1H NMR (400 MHz, chloroform-d) δ 7.79 (1 H, d, J=7.91 Hz), 7.46-7.53 (1 H, m), 7.38-7.44 (2 H, m), 7.30 (1 H, dd, J=7.91, 3.08 Hz), 7.14-7.26 (3 H, m), 6.77 (1 H, dd, J=7.69, 2.86 Hz), 4.59-4.74 (2 H, m), 3.39-3.54 (3 H, m), 2.72-2.80 (2 H, m), 2.30-2.44 (2 H, m), 1.80-2.10 (3 H, m), 1.75 (3 H, d, J=8.35 Hz). Mass spectrum m/z 466.1 (M+H)+.

Provenance & Evidence