(1-Bromoethyl)benzene → HCID 67224035, compound

Participants

Reaction Steps

Sodium hydride (4.74 mg, 0.119 mmol) was added at room temperature to 4-ethoxy-3-methyl-N-(2-methyl-4-oxo-1,3-diazaspiro[4.5]dec-1-en-8-yl)benzenesulfonamide (Example 471, 30 mg, 0.079 mmol) in DMF (988 μl). The reaction was stirred five minutes then a solution of (1-bromoethyl)benzene (16.18 μl, 0.119 mmol) in 200 ul DMF was added and the reaction stirred overnight at room temperature. After 16 hours, LCMS and HPLC indicated approximately 4:1 product:smarting material. The reaction was diluted with saturated sodium bicarbonate and extracted with multiple volumes ethyl acetate. The combined organics were rinsed 1× brine and dried over sodium sulfate. TLC (ethyl acetate) gave a product Rf 0.38 and starting material on the baseline. The crude was chromatographed on Biotage 12S by manual step gradient 7-100% EtOAc/heptane to yield the product as an off-white solid (21 mg). LCMS [M+H]=484.2.

Provenance & Evidence