6-CHLORO-5-AZAINDOLE

To a solution of 2-chloro-5-[(E)-2-ethoxyvinyl]pyridin-4-amine (preparation 36b, 1.00 g, 5.30 mmol) in methanol (20 mL) was added concentrated hydrochloric acid (1.00 mL, 32.64 mmol) and the mixture was stirred at 75 °C for 21 h. To a cooled solution of 2-chloro-5-((trimethylsilyl)ethynyl)pyridin-4-amine (1 g, I .0 eq) in DMF (10 mL) under nitrogen atmosphere in a microwave vial (20-30 mL, Biotage), potassium ie/t-butoxide was added portion wise and stirred for 5 min. The vial was closed and heated at 160°C in a microwave (Biotage synthesizer) for 50 min. The mixture was poured in water (10 mL) and extracted with EtOAc (2 x 25 mL). The organic layer was washed with brine (10 mL), dried over anhydrous sodium sulfate and concentrated to obtain the crude. The crude was purified by column chromatography (silica gel, 100-200) using EtOAc in hexane as eluent. The desired product eluted at 20percent EtOAc in hexane and concentration of the pure fractions provided 6-chloro-lH- pyrrolo[3, 2-c]pyridine as white solid (0.57 g, 85percent). 1H NMR (DMSO-dTo a solution of 6-Chloro-5-azaindole (1 g, 6.42 mmol) was partially suspended in 1, 4-dioxane (30 mL). DIPEA (3.5 mL, 20 mmol) was then added followed by triisopropylsilyl trifluoromethanesulfonate (2.5 mL, 9.3 mmol). The reaction mixture was stirred at room temperature for 5 h 30 min and then treated with an aq. work up. The organic solvent was dried (Na2SO4) and concentrated under reduced pressure to give a residue that was purified by flash silica column chromatography to give the title compound (1.68 g, 84%) which was used crude in the next step.Into a 50-mL round-bottom flask, was placed 6-chloro-lH-pyrrolo[3, 2-c]pyridine (500 mg, 3.28 mmol, 1.00 equiv), tetrahydrofuran (20 mL), sodium hydride (473 mg, 19.71 mmol, 6.00 equiv), 4-methylbenzene-l-sulfonyl chloride (937 mg, 4.91 mmol, 1.50 equiv). The resulting solution was stirred for 4 h at 80 C. The resulting solution was extracted with 200 mL of ethyl acetate and the organic layers combined and concentrated under vacuum. This resulted in 900 mg (crude) of the titl e compound that was used without further purification.

Molecular Weight:152.58
XLogP3:1.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:152.0141259
Monoisotopic Mass:152.0141259
Topological Polar Surface Area:28.7
Heavy Atom Count:10
Complexity:129
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes