5-METHYL-1H-PYRROLO[2,3-B]PYRIDINE

5-METHYL-1H-PYRROLO[2,3-B]PYRIDINE is Light yellow solid

Compound 2 (9.8 g, 48.0 mmol) and N-methylpyrrolidone (50 mL) were added to a three-necked flask;Sodium hydride (60percent, 2.8 g, 59 mmol) was added to the ice bath, 100 degrees Celsius for 10 minutes. Cool to room temperature, Saturated ammonium chloride solution (50 mL) was added and extracted with ethyl acetate (50 mL x 3); the organic phases were combined, washed with water (100 mL) and saturated brine (100 mL), dried over sodium sulphate and filtered. The filtrate was spin dried to give the crude product, which was recrystallized from ethyl acetate (10 mL) to give white solid, compound 3 (5.1 g, 38.6 mmol, 80percent).Step 2-Preparation of 5-methyl-1H-pyrrolo[2, 3-b]pyridine (15)To 5-Methyl-1-triisopropylsilanyl-1H-pyrrolo[2, 3-b]pyridine (14, 0.160 g, 0.55 mmol) in tetrahydrofuran (3.0 mL) was added tetra-n-butylammonium fluoride (0.145 g, 0.55 mmol). The reaction was stirred for 1 hour at room temperature. The reaction was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 3percent methanol in dichloromethane to provide light yellow solid (15, 0.07 g, 95percent). MS (ESI)[M+HTo 5-Methyl-l -triisopropylsilanyl-lH-pyrrolo[2, 3-b]pyridine (100, 0.16O g, 0.55 mmol) in tetrahydrofuran (3.0 mL) was added tetra-n-butylammonium fluoride (0.145 g, 0.55 mmol). The reaction was stirred for 1 hour at room temperature. The reaction was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 3percent methanol in dichloromethane to provide light yellow solid (101, 0.07 g, 95percent).Compound 2 (9.8 g, 48.0 mmol) and N-methylpyrrolidone (50 mL) were added to a three-necked flask;Sodium hydride (60percent, 2.8 g, 59 mmol) was added to the ice bath, 100 degrees Celsius for 10 minutes. Cool to room temperature, Saturated ammonium chloride solution (50 mL) was added and extracted with ethyl acetate (50 mL x 3); the organic phases were combined, washed with water (100 mL) and saturated brine (100 mL), dried over sodium sulphate and filtered. The filtrate was spin dried to give the crude product, which was recrystallized from ethyl acetate (10 mL) to give white solid, compound 3 (5.1 g, 38.6 mmol, 80percent).Step 2-Preparation of 5-methyl-1H-pyrrolo[2, 3-b]pyridine (15)To 5-Methyl-1-triisopropylsilanyl-1H-pyrrolo[2, 3-b]pyridine (14, 0.160 g, 0.55 mmol) in tetrahydrofuran (3.0 mL) was added tetra-n-butylammonium fluoride (0.145 g, 0.55 mmol). The reaction was stirred for 1 hour at room temperature. The reaction was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 3percent methanol in dichloromethane to provide light yellow solid (15, 0.07 g, 95percent). MS (ESI)[M+HTo 5-Methyl-l -triisopropylsilanyl-lH-pyrrolo[2, 3-b]pyridine (100, 0.16O g, 0.55 mmol) in tetrahydrofuran (3.0 mL) was added tetra-n-butylammonium fluoride (0.145 g, 0.55 mmol). The reaction was stirred for 1 hour at room temperature. The reaction was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 3percent methanol in dichloromethane to provide light yellow solid (101, 0.07 g, 95percent).

5-METHYL-1H-PYRROLO[2,3-B]PYRIDINE is an intermediate for preparation of pyrrolopyridine compounds as protein kinase modulators useful in treatment of diseases associated with aberrant activity of protein kinases.

Molecular Weight:132.16
XLogP3:1.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:132.068748264
Monoisotopic Mass:132.068748264
Topological Polar Surface Area:28.7
Heavy Atom Count:10
Complexity:124
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes