Dichloromethane → 5-pyridin-3-yl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole

Participants

Reaction Conditions

Reaction Steps

[1,1′-Bis(diphenylphosphino)-ferrocene)dichloropalladium(II) 1:1 complex with dichloromethane (204 mg, 0.25 mmol) was added to a mixture of 5-iodo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole (Preparation #17a, 1.87 g, 5.00 mmol), pyridine-3-boronic acid (737 mg, 6.00 mmol), and Cs2CO3 (4.89 g, 15.0 mmol) in 1,2-dimethoxy-ethane (16 mL) and water (3.2 mL) under a nitrogen atmosphere. The reaction was heated at about 100° C. overnight, cooled, concentrated and extracted with CH2Cl2 (about 30 mL). The extracts were adsorbed onto silica and purified over a silica gel column eluting first with heptane:EtOAc (85:15) and then with heptane:EtOAc (3:2) to yield 5-pyridin-3-yl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole (857 mg, 53%) as an oil. RP HPLC (Table 1, Method e) Rt=3.04, m/z: (MH)+ 326.

Provenance & Evidence