1-Methylpiperazine → 6-(4-methylpiperazin-1-yl)-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine

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Reaction Conditions

Reaction Steps

In a 25 mL round-bottomed flask, 6-bromo-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (520 mg, 1.47 mmol, Eq: 1.00), palladium (II) acetate (165 mg, 736 μmol, Eq: 0.5) and tri-tert-butylphosphine (149 mg, 182 μl, 736 μmol, Eq: 0.5) were combined with toluene to give a yellow solution. 1-methylpiperazine (442 mg, 491 μl, 4.41 mmol, Eq: 3) and sodium tert-butoxide (424 mg, 4.41 mmol, Eq: 3) were added. The reaction mixture was heated to 80° C. and stirred for 1 h. The reaction mixture was poured into 20 mL EtOAc and extracted with sat NaCl (3×20 mL). The organic layers were dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 12 g, 2% to 5% MeOH in DCM) to give 6-(4-methylpiperazin-1-yl)-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (326 mg, 60%) as yellow oil that solidified upon standing.

Provenance & Evidence