Methyl iodide → N-methyl-1H-pyrrolo[2,3-b]pyridin-5-amine

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Reaction Steps

1-Triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-5-ylamine (375 mg, 1.3 mmol) and triethylamine (271 μL, 1.95 mmol) in dichloromethane (10 mL) was treated with di-tert-butyl dicarbonate (340 mg, 1.5 mmol) and the mixture was stirred at RT for 2.5 h., quenched with saturated ammonium chloride (20 mL) and extracted with ethyl acetate (3×25 mL). The combined organic layers were washed with brine (50 mL), dried (MgSO4.), filtered and concentrated. The residue was purified by preparative HPLC. B. 1-Triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-carbamic acid tert-butyl ester (250 mg, 0.6 mmol) was then treated with sodium hydride (24 mg, 60% oil, 0.6 mmol) and methyl iodide (48 mL, 0.77 mmol) in DMF (2.0 mL). The mixture was stirred at RT for 16 h, quenched with saturated ammonium chloride (20 mL) and extracted with ethyl acetate (3×25 mL). The combined organic layers were washed with brine (50 mL), dried (MgSO4.), filtered and concentrated. The residue, which was used with no further purification, was then treated with TFA (1.0 mL) in dichloromethane (4.0 mL) and the mixture was stirred at RT for 10 h, concentrated and purified by preparative HPLC to afford methyl(1H-pyrrolo[2,3-b]pyridin-5-yl)-amine (31 mg, 33%). m/z 148 (M+H)+.

Provenance & Evidence