Ethyl Acetate → N-(5'-Bromo-4,4-difluorospiro[cyclohexane-1,2'-indene]-3'(1'H)-ylidene)-2-methylpropane-2-sulfinamide

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Reaction Conditions

Reaction Steps

6′-Bromo-4,4-difluorospiro[cyclohexane-1,2′-inden]-1′(3′H)-one (Intermediate 11, 819 mg, 2.60 mmol), 2-methylpropane-2-sulfinamide (630 mg, 5.20 mmol) and titanium ethoxide (1.874 mL, 9.10 mmol) were dissolved in 2-Me THF (9 mL) and heated to 120° C. with MW for 1 h. EtOAc (20 mL) and NaHCO3 (aq., sat, 2 mL) were added under stirring. The mixture was left to stand without stirring for 1 h. The organic phase was collected by filtration, dried over MgSO4 and concentrated. Flash chromatography with a gradient of 0-50% EtOAc in n-heptane gave the title compound (340 mg, 31% yield). 1 H NMR (500 MHz, DMSO-d6) δ ppm 1.25 (s, 9 H), 1.56-1.71 (m, 2 H), 2.10 (br. s., 6 H), 3.12 (s, 2 H), 7.49 (d, 1 H), 7.81 (dd, 1 H), 8.43-8.63 (m, 1 H). MS (ES+) m/z 418 [M+H]+.

Provenance & Evidence