5-METHOXY-6-AZAINDOLE Chemical Properties

Melting point:

122-127 °C

Boiling point:

304℃

Density 

1.244

Flash point:

105℃

storage temp. 

2-8°C

pka

14.36±0.40(Predicted)

form 

powder

Appearance

Off-white to gray Solid

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

WGK Germany 

3

HS Code 

2933998090

5-METHOXY-6-AZAINDOLE Usage And Synthesis

Uses

Reactant for preparation of indole sulfonamides as HIV entry inhibitors1Reactant for synthesis of melatoninergic ligands including azaindole moiety2

Uses

Reactant for preparation of indole sulfonamides as HIV entry inhibitors
Reactant for synthesis of melatoninergic ligands including azaindole moiety

Synthesis

Example 12: Synthesis of 5-methoxypyrrolo[2,3-c]pyridine (Compound 9) 4-Methyl-5-nitro-1H-pyridin-2-one (5.00 g, 32.44 mmol) was mixed with thionyl chloride (20 ml), two drops of dimethylformamide were added under nitrogen protection and heated to reflux for 52 hours. Upon completion of the reaction, the resulting orange solution was concentrated under reduced pressure, added a small amount of anhydrous toluene and concentrated again under reduced pressure to remove residual thionyl chloride. Subsequently, the crude product was purified by column chromatography on silica gel (silica gel was pre-dried overnight at 150 °C under vacuum, about 100 g), and the eluent was dichloromethane (11). The eluate was collected and concentrated under reduced pressure to afford 2-chloro-4-methyl-5-nitropyridine (5.30 g, 30.71 mmol, 95% yield) as an orange oil, which could be crystallized by cooling to below 0 °C. Product characterization data. IR (CHCl3): 1605, 1550, 1520, 1450, 1360, 1345 cm-1;. 1H NMR (CDCl3): δ 9.03 (s, 1H), 7.83 (s, 1H), 2.60 (s, 3H); δ 2.60 (s, 3H). LRMS (m/z, relative intensity): 174 (25), 173 (19), 172 (M+, 68), 157 (74), 155 (100), 128 (27), 101 (47), 100 (55), 99 (74), 90 (43), 75 (36).

References

[1] Patent: US5051412, 1991, A

5-METHOXY-6-AZAINDOLE(17288-53-8)Related Product Information

• 5-METHOXY-1H-PYRROLO[3,2-B]PYRIDINE
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• (5-METHOXY-1H-PYRROLO[2,3-C]PYRIDIN-2-YL)METHANOL
• 5-BENZYLOXY-1H-PYRROLO(2,3-C)PYRIDINE-3- CARBOXALDEHYDE, 97
• ETHYL 3-((DIMETHYLAMINO)METHYL)-5-METHOXY-1H-PYRROLO[2,3-C]PYRIDINE-2-CARBOXYLATE
• 3-(CYANOMETHYL)-5-METHOXY-1H-PYRROLO[2,3-C]PYRIDINE-2-CARBOXYLIC ACID
• 5-METHOXY-1H-PYRROLO[2,3-C]PYRIDINE-2-CARBOXYLIC ACID
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• 5-BENZYLOXY-6-AZAINDOLE
• 5-BENZYLOXY-1H-PYRROLO[2,3-C]PYRIDINE-3-CARBOXYLIC ACID METHYL ESTER
• RARECHEM AN KD 1444
• RARECHEM AN KB 1443
• RARECHEM AL BI 0778
• RARECHEM AL BP 0778
• RARECHEM AN KC 1432
• RARECHEM AN KA 1439
• 5-BENZYLOXY-1H-PYRROLO[2,3-C]PYRIDINE-3-CARBOXYLIC ACID
• RARECHEM AL BM 0778