Water → HCID 53836832, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-bromobenzaldehyde (300 mg, 1.62 mmol) in DMF (10 mL) are added 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (470 mg, 2.43 mmol), Pd(PPh3)4 (190 mg, 0.16 mmol) and 2M Na2CO3 (0.50 mL) at room temperature. The solution is heated to 100° C. for 1 hour in a microwave reactor, cooled and poured into water and EtOAc. Layers are separated and the aqueous phase extracted with EtOAc (1×10 mL). The combined organics are dried (MgSO4), filtered and are concentrated to give the crude product which is purified via flash chromatography (12 g silica gel, 0-10% MeOH/CH2Cl2). The product-containing fractions are combined and concentrated to give 2-(1H-pyrazol-4-yl)-benzaldehyde (110 mg, 39%) which is used without further purification.

Provenance & Evidence