Dichloromethane → HCID 86656201, compound

Participants

Reaction Conditions

Reaction Steps

5-isopropoxypyridine 2BIa (10 g, 0.046 mol), bis(pinacolato)diboron (14.1 g, 0.056 mol), potassium acetate (13.6 g, 0.14 mol) and PdCl2(dppf)2.CH2Cl2 (3.78 g, 0.0046 mol) were weight into a 2-necked 1 L flask equipped with a water condenser. DMSO (100 ml) was added and the mixture was purged with nitrogen for 15 min. The mixture was heated at 100° C. under nitrogen for 2 hr. After being cooled to r.t., water (100 ml), toluene (100 ml), ethanol (100 ml), potassium carbonate (32 g, 0.23 mol) and bromoindazole 3BI (22.4 g, 0.046 mol) were added. The mixture were purged with nitrogen for 10 min at r.t. and Pd(Ph3P)4 (5.35 g, 0.0046 mol) was added. The final mixture were heated at 100° C. for 2 hr and cooled to r.t. Water and ethyl acetate were added. Solids were filtered through Celite. Layers were separated and the separated organic layer was washed with water (×2). The combined aqueous layers were back extracted with ethyl acetate (×1). The combined organic layers were dried (MgSO4), filtered and solvents were removed in vacuum. Column purification [Hexanes-ethyl acetate=9:1 (v/v)] gave isopropoxyindazole 4BI (20 g, 80%) as yellow solid.

Provenance & Evidence