Ammonium Chloride → HCID 90311972, compound

Participants

Reaction Steps

To a solution of (S,Z)—N-((3-bromo-5-(1,3-dioxoisoindolin-2-yl)pyridin-2-yl)methylene)-2-methylpropane-2-sulfinamide (30C, 3.7 G, 8.5 mmol) and Cu(OTf)2 (154 mg, 0.4 mmol) in methylene chloride (30 ml) at 0° C. was added (3,5-difluorobenzyl)zinc bromide (0.5 M in THF, 25.5 ml, 12.8 mmol) dropwise. The reaction stirred at room temperature for one hour. Ammonium chloride (aq, 100 ml) was added to the reaction and the mixture was extracted with methylene chloride (2×100 ml). The organic layer was dried over Na2SO4 filtered and concentrated (about 1:3 ratio of two diastereomers). The crude was purified by reverse phase HPLC eluting with acetonitrile and water (with 0.1% TFA) to afford the title compound as a single diastereomer. MS (m/z) 563.83 [M+H]+.

Provenance & Evidence