5-Bromo-7-azaindole CAS#: 183208-35-7; 凯望编码 (ChemWhat Code): 13855

IdentificationPhysical DataSpectra
Route of Synthesis (ROS)Safety and HazardsOther Data

Identification

英文名5-Bromo-7-azaindole
IUPAC Name5-bromo-1H-pyrrolo[2,3-b]pyridine
分子结构
CAS编号 183208-35-7
EINECS Number629-247-8
MDL NumberMFCD06659677
Beilstein Registry Number8253948
别名5-bromo-1H-pyrrolo[2,3-b]pyridine, 5-Bromo-1H-pyrrolo[2,3-b]pyridine, tert-butyl 5-bromo-1H-pyrrolo[2,3-b]pyridine-1-carboxylate, 5-bromo-1H-pyrrolo<2,3-b>pyridine, 5-bromo-1H-pyrrolo[2, 3-b]pyridine, 5-bromo-1H-pyrrolo[2,3-b]-pyridine, 5-bromo-1H-pyrrolo(2,3-b)pyridine
5-Bromo-7-azaindole CAS#: 183208-35-7
CAS#: 183208-35-7
分子式C7H5BrN2
分子量197.03
InChIInChI=1S/C7H5BrN2/c8-6-3-5-1-2-9-7(5)10-4-6/h1-4H,(H,9,10)
InChI KeyLPTVWZSQAIDCEB-UHFFFAOYSA-N
Canonical SMILESC1=CNC2=NC=C(C=C21)Br
Patent Information
Patent IDTitlePublication Date
US2013/245355 3-HETARYL-SUBSTITUTED PYRROLO[2,3 B]PYRIDINE DERIVATIVES AS PDK1 INHIBITORS2013
US2014/275082 APOPTOSIS-INDUCING AGENTS FOR THE TREATMENT OF CANCER AND IMMUNE AND AUTOIMMUNE DISEASES 2014
US2015/11533 1H-PYRROLO[2,3-B] PYRIDINE DERIVATIVES AND THEIR USE AS KINASE INHIBITORS 2015
US2015/183781 5-(1H-Pyrazol-4-yl)-1H-Pyrrolo[2,3-b]Pyridine Derivatives as Kinase Inhibitors2015
US2011/28511 PROCESS FOR THE MANUFACTURE OF PHARMACEUTICALLY ACTIVE COMPOUNDS 2011

Physical Data

AppearanceWhite to yellow Crystalline Powder
SolubilityNo data available
Flash PointNo data available
Refractive indexNo data available
SensitivityNo data available
Melting Point, °C Solvent (Melting Point)
176.8 – 177.3
178.2 – 178.9
174 – 176
176 – 177 pentane
Density, g·cm-3Measurement Temperature, °CType (Density)
1.861 25.84 crystallographic

Spectra

Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)Frequency (NMR Spectroscopy), MHz
Chemical shifts, Spectrum1Hchloroform-d1300
Chemical shifts1Hdimethylsulfoxide-d6 300
Chemical shifts 1Hdimethylsulfoxide-d6
Chemical shifts 1Hchloroform-d1 500
Chemical shifts 1Hchloroform-d1 400
Chemical shifts 13Cchloroform-d1 100
Spectrum 1HCDCl3 400
Chemical shifts 1HCDCl3 400
Chemical shifts 13CCDCl3 100
Chemical shifts 1HCDCl3 300
Description (IR Spectroscopy)Solvent (IR Spectroscopy)Comment (IR Spectroscopy)
Bandspotassium bromide
ATR (attenuated total reflectance), Spectrum
Intensity of IR bands, Bands
ATR (attenuated total reflectance), Bands
Mid IR (MIR), Bands potassium bromide
Bands KBr
Bands KBr 3300 – 3000 1/cm
Description (Mass Spectrometry) Comment (UV/VIS Spectroscopy)Peak
liquid chromatography mass spectrometry (LCMS), spectrum
electron impact (EI), spectrum
high resolution mass spectrometry (HRMS), electron impact (EI), spectrum
LCMS (Liquid chromatography mass spectrometry) Molecular peak 198.04 m/z
ESI (Electrospray ionisation)
LCMS (Liquid chromatography mass spectrometry) Molecular peak
Molecular peak
Molecular peak 197 m/z
Description (Raman Spectroscopy)
Bands, Spectrum

Route of Synthesis (ROS)

Route of Synthesis (ROS) of 5-Bromo-7-azaindole CAS 183208-35-7
Route of Synthesis (ROS) of 5-Bromo-7-azaindole CAS 183208-35-7
ConditionsYield
With manganese(IV) oxide In dichloromethane for 72h;

Experimental Procedure
To a stirred solution of azaindoline 5 (7.00 g, 35.2 mmol) in CH2C12 (664 ML) was added activated MnO2 (3.06 g, 35.2 MMOL), AND PROGRESS of the reaction was monitored BY LH EMR of reaction aliquots. After 3 days the mixture was filtered through A pad of silica, and the pad was washed with EtOAc. The filtrates were concentrated to afford the azaindole 27 (6. 98 g, 100 percent) as A brown solid. 1H NMR data as in Method 1. 		100%
With manganese(IV) oxide In toluene for 4h; Reflux;

Experimental Procedure
The 84.8 g of the 5-bromo-7-azaindoline product obtained in step 4 was dissolved in 400 mL of toluene,221.5 g of manganese dioxide was added,Heating reflux reaction 4h;Step 6) The reaction solution obtained in Step 5 was cooled to room temperature,filter,The filter cake was washed twice with dichloromethane,Combine organic phase,dry,Concentrated 5-bromo-7-azaindole crude product,The product was crystallized from a petroleum ether-ethyl acetate mixed solution of ΡΕ / ΕΑ = 10: 1 to give 75 g of 5-bromo-7-azaindole,Yield 90percent. 		90%
With activated carbon fiber catalyst In 5,5-dimethyl-1,3-cyclohexadiene at 100℃; for 8h; Solvent;

Experimental Procedure
a) 30g (0.151mol) of 5-bromo-7-azaporphyrin, 60g of activated carbon fiber catalyst, 264g of xylene into the reaction flask, stirring evenly, to obtain a reaction mixture G;b) The reaction mixture G at 100 °C, oxygen flow 200mL/min, reaction 8h, chromatographic monitoring of the disappearance of raw materials;c) Filtration, filter out activated carbon fiber catalyst, obtain organic layer H, recover solvent, get 5-bromo-7-azaindole crude product, recrystallize from methanol to obtain product 25.37g, yield 85.43percent, content ≥99percent . 		85.43%

Safety and Hazards

Pictogram(s)exclamation-markcorrosion
SignalDanger
GHS Hazard StatementsH302 (84.85%): Harmful if swallowed [Warning Acute toxicity, oral]
H315 (18.18%): Causes skin irritation [Warning Skin corrosion/irritation]
H318 (84.85%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
H319 (12.12%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (15.15%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
Information may vary between notifications depending on impurities, additives, and other factors.
Precautionary Statement CodesP261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501
(The corresponding statement to each P-code can be found at the GHS Classification page.)

Other Data

TransportationNONH for all modes of transport
Under the room temperature and away from light
HS Code293399
StorageUnder the room temperature and away from light
Shelf LifeNo data available
Market PriceUSD
Use Pattern
5-Bromo-7-azaindole CAS#: 183208-35-7 Used as Vemurafenib intermediate.

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