1,2-Dibromoethane → HCID 66604616, compound

Participants

Reaction Steps

A 100 ml round bottom flask was loaded with tert-butyl 4-(8-carbamoyl-6-(3-chloro-4-hydroxyphenyl)-9H-carbazol-2-yl)piperazine-1-carboxylate (estimated purity ˜50%, 365 mg, ˜0.35 mmol, Example 409B), K2CO3 (1.12 g, 8.10 mmol), DMF (20 ml) and 1,2-dibromoethane (0.64 ml, 7.4 mmol) and stirred at room temperature for 17 hours. The reaction mixture was poured into a separating funnel that was loaded with 500 ml water+citric acid (0.5 M solution in water) (60 ml, 30 mmol) and extracted with ethyl acetate. The organic layer was washed with dilute (1+5) aq. NaHCO3 solution, then brine, dried over MgSO4, filtered and evaporated to dryness to give 342 mg tert-butyl 4-(6-(4-(2-bromoethoxy)-3-chlorophenyl)-8-carbamoyl-9H-carbazol-2-yl)piperazine-1-carboxylate, which was used without further purification. Estimated purity (from LCMS) ˜55%. MS (ESI) m/e+=627/629/631, m/e−=625/627/629 consistent with isotope pattern for 1 Br and 1 Cl.

Provenance & Evidence