4-FLUORO-7-AZAINDOLE Chemical Properties

Melting point:

118-120°C

Density 

1.370±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,2-8°C

solubility 

Dichloromethane, Ethyl Acetate, Methanol, THF

form 

Solid

pka

13.28±0.40(Predicted)

color 

Off-White to Pale Yellow

InChI

InChI=1S/C7H5FN2/c8-6-2-4-10-7-5(6)1-3-9-7/h1-4H,(H,9,10)

InChIKey

YZTWCWYRUCKWDR-UHFFFAOYSA-N

SMILES

C12NC=CC1=C(F)C=CN=2

Safety Information

HS Code 

2933998090

4-FLUORO-7-AZAINDOLE Usage And Synthesis

Chemical Properties

Off-White Solid

Uses

4-Fluoro-7-azaindole (cas# 640735-23-5) is a compound useful in organic synthesis.

Synthesis

Under argon protection, 4-fluoro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (3 g, 10 mmol) was dissolved in THF (15 mL) and cooled to 0°C. To this solution was slowly added a THF solution of tetrabutylammonium fluoride (1 M, 10.5 mL). The reaction mixture was gradually warmed to room temperature and stirred continuously for 1 hour. The progress of the reaction was monitored by TLC and after confirming complete consumption of the raw material, the reaction mixture was diluted with water (50 mL) and extracted with ethyl acetate (2 x 100 mL). The organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography with 20% ethyl acetate/hexane as eluent to afford 4-fluoro-1H-pyrrolo[2,3-b]pyridine (1.3 g, 94% yield) as an off-white solid.1H NMR (CDCl3, 400MHz): δ 10.52 (brs, 1H), 8.30-8.25 (m, 1H), 7.32-7.30 (m , 1H), 6.81 (dd, 1H), 6.59 (s, 1H); TLC: 20% EtOAc/hexane (Rf = 0.2).

References

[1] Organic Letters, 2003, vol. 5, # 26, p. 5023 - 5025
[2] Tetrahedron Letters, 2007, vol. 48, # 9, p. 1527 - 1529
[3] Patent: WO2017/31325, 2017, A1. Location in patent: Paragraph 0722

4-FLUORO-7-AZAINDOLE(640735-23-5)Related Product Information

• 1H-Pyrrolo[2,3-b]pyridine, 6-fluoro-
• 6-NITRO-1H-PYRROLO[2,3-B]PYRIDINE
• 4-METHYL-7-AZAINDOLE
• 1,7-DIDEAZAADENINE
• 1H-PYRROLO[2,3-B]PYRIDINE-6-CARBONITRILE
• 7-Azaindole
• 6-FLUORO-7-AZAINDOLE
• 5-FLUORO-7-AZAINDOLE
• 4-FLUORO-7-AZAINDOLE
• 4-FLUORO-1-(PHENYLSULFONYL)-1H-PYRROLO[2,3-B]PYRIDINE