Sodium Chloride → N1,N1-dimethyl-N2-(1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-6-yl)ethane-1,2-diamine

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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 (713 mg, 2.02 mmol, Eq: 1.00), N,N-dimethylethylenediamine (1.07 g, 1.32 ml, 12.1 mmol, Eq: 6) and bis(tri-tert-butylphosphine)palladium(0) (206 mg, 404 μmol, Eq: 0.2) were combined with toluene (2 ml) to give a yellow solution. Sodium tert-butoxide (582 mg, 6.05 mmol, Eq: 3) was added. The reaction mixture was heated to 80° C. and stirred for 1 h, then poured into 20 mL sat NaCl and extracted with EtOAc (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 N1,N1-dimethyl-N2-(1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-6-yl)ethane-1,2-diamine (405 mg, 56%) as yellow oil that solidified upon standing.

Provenance & Evidence