Chlorotrimethylsilane → HCID 86666945, compound

Participants

Reaction Conditions

Reaction Steps

Zinc (4.5 g, 69 mmol) was suspended with 1,2-dibromoethane (420 pt, 4.9 mmol) in DMF (54 mL). The mixture was heated at 70° C. for 10 min and then cooled to room temperature. Chlorotrimethylsilane (6204, 4.9 mmol) was added dropwise and stirring was continued for 1 hour. A solution of tert-butyl 3-iodoazetidine-1-carboxylate (17 g, 61 mmol) in DMF (30 mL) was then added and the mixture was heated at 40° C. for 1 h before a mixture of 1-(4,5-dichloro-3-iodo-2-methoxyphenyl)ethanone (14 g, 41 mmol), tris(dibenzylideneacetone)dipalladium(0) (710 mg, 0.77 mmol) and tri-(2-furyl)phosphine (360 mg, 1.6 mmol) in DMF (120 mL) was added quickly. The reaction mixture was stirred overnight at room temperature. The reaction mixture was then partitioned between EtOAc and saturated ammonium chloride solution. The organic layer was washed with water, dried with magnesium sulfate, filtered, and concentrated to a crude residue that was purified by flash column chromatography using EtOAc in hexanes (0%-25%) to give the desired product (12 g, 77%). LCMS for C17H21Cl2NO4Na (M+Na)+: m/z=396.1. Found: 396.0.

Provenance & Evidence