4-Bromopyridinium chloride → HCID 71611179, compound

Participants

Reaction Conditions

Reaction Steps

619 mg of 2-[1-(4-ethoxy-2,6-difluorobenzyl)-5-methoxy-4-methyl-1H-pyrazol-3-yl]-5-methoxypyrimidin-4-amine 1-5-1 (1.53 mmol, 1.0 eq.), 445-38 mg of 4-bromopyridine hydrochloride (1:1) (2.29 mmol, 1.5 eq.), 190.15 mg of (R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphtyl (305 mmol, 0.2 eq.), 587 mg of sodium-tert-buylat (6.12 mmol, 4.0 eq.) and 419 mg of tris-(dibenzylideneacetone)dipalladium(0) (0.458 mmol, 0.3 eq.) were suspended in 10 mL of dry DMF and stirred under nitrogen atmosphere at 110° C. bath temperature for 24 hours. The reaction mixture was partitioned between half saturated aqueous ammonium chloride solution and DCM. The separated aqueous layer was extracted twice with DCM. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography (hexane (0-100%)/ethyl acetate). The column was washed with methanol to receive a 50% pure target compound. This was stirred with acetone and the suspension was filtered off.

Provenance & Evidence