Bromide ion → HCID 59299909, compound

Participants

Reaction Steps

To a solution of 2-(4-Bromo-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (400 mg, 1.18 mmol) in toluene (4 mL) is added Pd2(dba)3.CHCl3 (50 mg, 0.05 mmol) and P(tBu)3 (40 mg, 0.20 mmol). The mixture is degassed at −30° C. KHMDS (7.0 mL, 0.5 M solution in toluene, 3.5 mmol)) is added to the flask. The resulting mixture is stirred at room temperature overnight. TLC is used to detect when the starting bromide is consumed, the reaction mixture is diluted with ether and poured into dilute HCl (aq). The ether layer is discarded, the aqueous layer is basified with NH4OH and extracted with CH2Cl2. The CH2Cl2 layer is dried and concentrated. The residue (300 mg) is directly employed in the next step.

Provenance & Evidence