Dichloromethane → HCID 135997584, compound

Participants

Reaction Steps

[1,1′-Bis(diphenylphosphino)-ferrocene)dichloropalladium(II) 1:1 complex with dichloromethane (40.8 mg, 0.05 mmol) was added to a mixture containing 5-bromo-3-(1H-pyrrol-2-yl)-1H-indazole (Preparation #16c, 105 mg, 0.40 mmol), aqueous pyridine-3-boronic acid (1M, 1.0 mL), and Cs2CO3 (391 mg, 1.20 mmol) in DMF (2.0 mL) under a nitrogen atmosphere was added and the mixture was purged with N2 again, then heated at reflux for about 3 days. The reaction was cooled to ambient temperature and the organic layer was filtered through silica gel and concentrated under reduced pressure. The residue was further purified by preparative HPLC (Thermo Hypersil-Keystone 250×21.2 mm 8μ Hypersil® HS C18 column; 5% CH3CN/50 mM aqueous ammonium acetate hold for 5 min; 5-50% CH3CN/50 mM aqueous ammonium acetate over 20 min; 50-100% CH3CN/50 mM aqueous ammonium acetate over 1 min; hold at 100% CH3CN for 5 minutes, 21 mL/min). Product fractions were combined and concentrated to remove organic solvents and the lyophilized to yield 5-pyridin-3-yl-3-(1H-pyrrol-2-yl)-1H-indazole (44 mg, 42%) as an off-white powder. RP HPLC (Table 1, Method e) Rt=2.23; m/z: (MH)+ 261.

Provenance & Evidence