ChemicalBook--->CAS DataBase List--->5654-93-3

5654-93-3

5654-93-3 Structure

5654-93-3 Structure
IdentificationBack Directory
[Name]

3-METHYL-7-AZAINDOLE
[CAS]

5654-93-3
[Synonyms]

7-Azaskatole
3-METHYL-7-AZAINDOLE
3-METHYL-7-AZAINDOLE(LR)
3-Methylpyrrolo[2,3-b]pyridine
3-methyl-1H-pyrrolo[2,3-b]pyridine
1H-Pyrrolo[2,3-b]pyridine, 3-methyl-
3-Methyl-1H-pyrrolo[2,3-b]pyridine 98%
[Molecular Formula]

C8H8N2
[MDL Number]

MFCD08272239
[MOL File]

5654-93-3.mol
[Molecular Weight]

132.16
Chemical PropertiesBack Directory
[Melting point ]

130.5-133 °C
[Boiling point ]

352.8±15.0 °C(Predicted)
[density ]

1.17±0.1 g/cm3(Predicted)
[storage temp. ]

Sealed in dry,Room Temperature
[pka]

8.01±0.20(Predicted)
[Appearance]

Off-white to yellow Solid
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P301+P312+P330-P302+P352-P305+P351+P338
[HS Code ]

2933399990
Hazard InformationBack Directory
[Uses]

An azaindole derivative as CRTH2 receptor antagonist.
[Synthesis]

2,3-Dichloropyridine

2402-77-9

Allylamine

107-11-9

3-METHYL-7-AZAINDOLE

5654-93-3

(Synthesis of (a) 3-methyl-1H-pyrrolo[2,3-b]pyridine: The intermediate was prepared by the method described by Jensen et al. (Angew. Chem. Int. Ed. 2008, 47, 888-890). Toluene (5 mL), 2,3-dichloropyridine (300 mg, 2.03 mmol), tris(dibenzylideneacetone)dipalladium (Pd2dba3, 2 mg, 0.0025 mmol), 1,1'-bis(diphenylphosphino)ferrocene (dppf, 6 mg, 0.01 mmol), sodium tert-butoxide (NaOtBu, 487 mg , 5.07 mmol) and allylamine (0.15 mL, 2.03 mmol). The reaction tube was sealed and heated at 140 °C for 20 h, followed by stirring for 24 h at room temperature. The reaction mixture was washed sequentially with water and brine, dried over anhydrous sodium sulfate (Na2SO4) and adsorbed on silica gel. Initial purification was carried out using a gradient elution of dichloromethane-hexane (0 to 60%) followed by ethyl acetate-hexane (80%) to give an orange solid product (100 mg, 37% yield).

[References]

[1] Angewandte Chemie - International Edition, 2008, vol. 47, # 5, p. 888 - 890
[2] Patent: WO2010/132615, 2010, A1. Location in patent: Page/Page column 111
[3] Patent: WO2013/114332, 2013, A1. Location in patent: Page/Page column 92; 93
[4] Patent: US2014/371204, 2014, A1. Location in patent: Paragraph 0718
Spectrum DetailBack Directory
[Spectrum Detail]

3-METHYL-7-AZAINDOLE(5654-93-3)1HNMR
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