Bromide ion → HCID 44451358, compound

Participants

Reaction Conditions

Reaction Steps

(PPh3)2PdCl2 (4 mg, 0.006 mmol), ferrocene palladium dichloride (6 mg, 0.009 mmol) and 2-pyridylzine bromide (2 mL, 1.0 mmol) were added to a solution of (11β,16α,17β)-11-(4-bromophenyl)-17-cyclopropylcarbonyl-16-methylestra-4,9-dien-3-one (200 mg, 0.41 mmol) in THF (4 mL) under a nitrogen atmosphere. The reaction mixture was stirred for 5 hours at 60° C. and then cooled to room temperature. A saturated aqueous NH4Cl solution was added and the mixture was extracted three times with dichloromethane. The combined organic layers were dried through a phase separate filter and evaporated to dryness. Purification by HPLC followed by lyophilisation gave (11β,16α,17β)-17-cyclopropylcarbonyl-16-methyl-11-[4-(2-pyridinyl)phenyl]estra-4,9-dien-3-one (80 mg, 0.16 mmol, 40% yield). 1H NMR (400 MHz, CDCl3): δ 0.33 (s, 3H), 0.80-2.87 (m, 24H), 4.46 (d, J=7 Hz, 1H), 5.80 (s, 1H), 7.20-7.23 (m, 1H), 7.25-7.29 (m, 2H), 7.68-7.77 (m, 2H), 7.89-7.92 (m, 2H), 8.67 (dt, J=5 and 1 Hz, 1H).

Provenance & Evidence