Chlorotrimethylsilane → HCID 86644578, compound

Participants

Reaction Conditions

Reaction Steps

An oven dried glass vial was charged with zinc powder (120 mg, 1.837 mmol). THF (0.5 mL) was added, followed by 1,2-dibromoethane (15 μL, 0.17 mmol), and the resulting mixture was placed in a pre-heated (65° C.) oil bath. After 10 min, the mixture was allowed to cool to room temperature, TMSCl (18 μL, 0.141 mmol) was added, and the resulting mixture was stirred at room temperature. After 30 min, a solution of tent-butyl 3-iodoazetidine-1-carboxylate (400 mg, 1.41 mmol) in THF (1 mL) was added, and the mixture was stirred at room temperature. After 45 min, a solution of tris(dibenzylideneacetone)dipalladium (65 mg, 0.071 mmol) and tri(2-furyl)phosphine (66 mg, 0.283 mmol) in THF (1 mL) was added, followed by a solution of methyl 4-iodobenzoate (444 mg, 1.70 mmol) in THF (1 mL). The septum and nitrogen inlet were quickly replaced with a teflon cap, and the reaction mixture was heated at 65° C. After 18 h, the mixture was allowed to cool to room temperature, then was diluted with EtOAc and poured in sat aq NaHCO3. The organic phase was separated and concentrated in vacuo. Purification by flash chromatography on silica gel (0 to 25% EtOAc in hexanes, then 25 to 100% EtOAc in hexanes) provided the title compound: LCMS m/z 235.9 [M-tBu]+; 1H NMR (500 MHz, CDCl3) δ 8.02 (d, J=8.5 Hz, 2H), 7.39 (d, J=8.5 Hz, 2H), 4.35 (t, J=7.5 Hz, 2H), 3.99-3.95 (m, 2H), 3.92 (s, 3H), 3.81-3.76 (m, 1H), 1.47 (s, 9H).

Provenance & Evidence