Nitrogen → HCID 9822422, compound

Participants

Reaction Steps

A suspension of zinc (0.18 g, 2.76 mmoles) in THF/toluene 2:1 (15 ml), under stirring and N2 under reflux, was added with 2-bromothiazole (0.23 ml, 2.5 mmoles). After 2½ hours 4-bromo-1-(3,5-dichloro-pyridin-4-ylmethyl)-6-methoxy-phthalazine (0.5 g, 1.25 mmoles), prepared as described in example 46, palladium acetate (14 mg, 0.0625 mmole) and triphenylphosphine (32 mg, 0.125 mmole) were added to the cold mixture. The mixture was refluxed for further 30 minutes. After 21 hours the same amounts of palladium acetate and triphenylphosphine were added. After 3 hours under reflux the mixture was cooled and poured into water/ice and NH4Cl, then extracted first with ethyl acetate, then with CH2Cl2. The organic phase was washed with water, anhydrified and concentrated to give a solid which was flash chromatographed (eluent: hexane/ethyl acetate 7:8) to give 0.26 g of the title compound (yield: 51%). m.p.: 225-230° C.

Provenance & Evidence