1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → HCID 58266748, compound

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Reaction Conditions

Reaction Steps

A suspension of 3,6-dibromo-9H-dipyrido[2,3-b;4′,3′-d]pyrrole (9.3 mg, 28 μmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (17.8 mg, 85.3 μmol) and bis(triphenylphosphine)palladium(II) dichloride (1.0 mg, 14 μmol) in acetonitrile (0.18 mL) and 2N aqueous sodium carbonate solution was heated under microwave irradiation at 140° C. for 20 minutes. The reaction mixture was allowed to cool to ambient temperature and the resultant precipitate collected by filtration, and the solid washed sequentially with water, DCM, and 20% MeOH in DCM. The filtrate was combined, the layers separated, and the aqueous phase extracted into 20% MeOH inDCM. The combined organic phase was concentrated in vacuo and the resultant residue purified by flash chromatography (silica, 0-20% MeOH in DCM) to afford the title compound. 1H NMR (DMSO-D6, 400 MHz): 12.01 (s, 1H), 8.83 (m, 2H), 8.78 (m, 1H), 8.39 (s, 1H), 8.21 (d, J=9.4 Hz, 2H), 7.97 (d, J=7.0 Hz, 2H), 3.98-3.91 (s, 6H). LCMS (Method D): RT=7.53 min, M+H+=330.

Provenance & Evidence