Potassium Iodide → HCID 72189888, compound

Participants

Reaction Conditions

Reaction Steps

4-(aminomethyl)-N-(2,4-dimethylphenyl)-N-isobutylbenzenesulfonamide (25 mg, 0.072 mmol), (tetrahydro-2H-pyran-4-yl)methanol (16.76 mg, 0.144 mmol), potassium iodide (23.95 mg, 0.144 mmol) and [Cp*IrCl2]2 (1.150 mg, 1.443 μmol) were dissolved in water (2 mL) in a microwave vial. The reaction vessel was sealed and heated by microwaves (Biotage Initiator) to 150° C. for 1 hour. After analysis the reaction vessel was resealed and heated again by microwaves (Biotage Initiator) to 150° C. for a further 1 hour. After further analysis an additional 1 eq of [Cp*IrCl2]2 and 1 eq of (tetrahydro-2H-pyran-4-yl)methanol were added and the reaction heated for a third time by microwaves (Biotage Initiator) to 150° C. for 1 hour. The reaction was cooled and the mixture concentrated in vacuo (Biotage V10). The crude product was extracted to the organic phase of an aqueous workup between ethyl acetate (5 mL) and water (5 mL). The organic phase was passed through a hydrophobic frit and concentrated in vacuo. The crude was purified by mass directed autoprep (formic acid modifier). The appropriate fractions were evaporated in vacuo (Biotage V10) to give the required product, 1.2 mg. LCMS [LCMS1] Rt 0.97 min, m/z (ES+) 445 (M+H).

Provenance & Evidence