6-Chloro-3-iodo-1H-pyrrolo[3,2-c]pyridine

Into a 100 mL 3-necked round-bottom flask was added a solution of 6-chloro- lH-pyrrolo [3, 2- c]pyridine (1.00 g, 6.55 mmol) in N, N-dimethylformamide (10 mL), potassium hydroxide (1.40 g, 24.9 mmol). The reaction mixture was stirred for 20 min at room temperature, then Ia) Preparation of intermediate 10A stirred solution of Into a 100 mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was added a solution of 6-chloro-3-iodo-lH-pyrrolo[3, 2-c]pyridine (1.70 g, 6.10 mmol) in N, N-dimethylformamide (20.0 mL) followed by sodium hydride (600 mg, 25.0 mmol). This was followed by addition of 2-iodopropane (2.20 g, 12.9 mmol) dropwise with stirring at 0 C. The reaction mixture was stirred for 16 h at room temperature. The reaction was then quenched by addition of water (50mL). The resulting solution was extracted with ethyl acetate (3x50 mL) and the organic layers were separated and combined. The combined organic layer was washed with brine (100 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1 :7) to afford the title compound (1.40 g, 72.0 %) as a yellow solid. LCMS (ESI): RT (min) = 1.549, [M+H]+ = 321, method = M.

Molecular Weight:278.48
XLogP3:2.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:277.91077
Monoisotopic Mass:277.91077
Topological Polar Surface Area:28.7
Heavy Atom Count:11
Complexity:155
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes