271-34-1

Basic information

• Product Name: 5-Azaindole
• Synonyms: 5-Aza-1H-indole;5-Azaindole (1,5-Diazaindene 3,7-Dideazapurine);5-Azaindole ,98%;5-Azaindole,1H-pyrrolo[3,2-c]pyridine;HARMYRINE;1H-PYRROLO[3,2-C]PYRIDINE;1,6-DIAZAINDENE;1,5-DIAZAINDENE
• CAS NO: 271-34-1
• Molecular Formula: C₇H₆N₂
• Molecular Weight: 118.14
• EINECS: 1312995-182-4
• Product Categories: Azaindole;Building Blocks;Azaindoles;Heterocycle-Indole series;Indoles and derivatives;Indole;Heterocyclic Compounds;Indole Series
• Mol File: 271-34-1.mol
• Article Data: 25

Chemical Properties

• Melting Point: 104.6-108.4°C
• Boiling Point: 132°C/0.2mmHg(lit.)
• Flash Point: 137.4 °C
• Appearance: /
• Density: 1.242 g/cm³
• Vapor Pressure: 0.003mmHg at 25°C
• Refractive Index: 1.697
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 15.20±0.30(Predicted)
• Water Solubility: Hardly soluble in water. Soluble in methanol and chloroform.
• CAS DataBase Reference: 5-Azaindole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Azaindole(271-34-1)
• EPA Substance Registry System: 5-Azaindole(271-34-1)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-41-37/38-22
• Safety Statements: 26-36/37/39-39
• RTECS: UY8725000
• Hazardous Substances Data: 271-34-1(Hazardous Substances Data)

Usage

Chemical Properties

crystals

Uses

Different sources of media describe the Uses of 271-34-1 differently. You can refer to the following data:
1. 5-Azaindole is a factor VIIa inhibitor.Also useful intermediate for pharmaceutical application.
2. 5-Azaindole is a factor VIIa inhibitor. Also useful intermediate for pharmaceutical application.

Synthesis Reference(s)

Tetrahedron, 49, p. 2885, 1993 DOI: 10.1016/S0040-4020(01)80387-2

InChI:InChI=1/C7H6N2/c1-4-9-7-2-3-8-5-6(1)7/h1-5,9H

Synthetic route

4-chloro-1H-pyrrolo-[3,2-c]-pyridine (60290-21-3) → 5-azaindole (271-34-1)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol	96%

tert-butyl 1H-pyrrolo[3,2-c]pyridine-1-carboxylate (148760-75-2) → 5-azaindole (271-34-1)

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 20℃; for 1.5h;	95%

3-(4-Morpholinovinylene)-4-nitropyridine 1-oxide (148760-46-7) → 5-azaindole (271-34-1)

Conditions	Yield
With hydrogen; nickel In ethanol; water under 14.7 - 22.07 Torr; 1) 15 h, 20 deg C, 2) 3-5 h, 60 deg C;	92%

3-Dimethylaminovinylene-4-nitropyridine (148760-47-8) → 5-azaindole (271-34-1)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol under 14.7 - 22.07 Torr; 1) 1 h, 20 deg C, 2) 3 h, 60 deg C;	91%

(E)-N,N-dimethyl-2-(4-nitro-1-oxidopyridin-3-yl)ethenamine (123367-22-6) → 5-azaindole (271-34-1)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In ethanol at 60℃; under 3750.38 Torr; for 4h; Inert atmosphere;	91%
With hydrogen; palladium on activated charcoal In ethanol under 14.7 - 22.07 Torr; 1) 1 h, 20 deg C, 2) 3 h, 60 deg C;	87%
With hydrogen; Raney nickel In ethanol; water at 20 - 40℃; under 750.075 Torr; for 5.25h;	76%

4-amino-3-chloropyridine (19798-77-7) + acetylene (74-86-2) → 5-azaindole (271-34-1)

Conditions	Yield
With Ni(1,5-cyclooctadiene)2 In tetrahydrofuran; diethyl ether at 110℃; for 4.5h; Temperature; Microwave irradiation;	90.4%

N-(3-((Z)-2-ethoxyvinyl)pyridin-4-yl)acetamide (146336-80-3) → 5-azaindole (271-34-1)

Conditions	Yield
With hydrogenchloride In methanol for 2h; Heating;	90%
With hydrogenchloride In methanol; water for 5h; Inert atmosphere; Reflux;	1.9 g

raney's nickel + 3-(β-dimethylaminovinyl)-4-nitro-pyridine-1-oxide → 5-azaindole (271-34-1)

Conditions	Yield
In ethanol; water	84%

3-ethynyl-4-pyridinamine (1239605-12-9) → 5-azaindole (271-34-1)

Conditions	Yield
With pyrrolidine In water at 200℃; for 0.25h; Microwave irradiation;	82%

3-dimethylaminovinylene-4-nitropyridine-l-oxide (104118-88-9) → 5-azaindole (271-34-1)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In ethanol at 20 - 65℃; under 1500.15 - 2250.23 Torr; for 8h; Inert atmosphere; Autoclave;	74.5%

N-(3-methyl-[4]pyridyl)-formamide (101870-39-7) + sodium formate (141-53-7) + sodium anilide (1865-45-8) → 5-azaindole (271-34-1)

Conditions	Yield
at 300℃;

N-(3-methyl-[4]pyridyl)-formamide (101870-39-7) → 5-azaindole (271-34-1)

Conditions	Yield
With sodium formate; sodium anilide at 290 - 310℃;

1H-pyrrole[3,2-C]pyridine-3-carboxylic acid (119248-43-0) → 5-azaindole (271-34-1)

(3-Trimethylsilanylethynyl-pyridin-4-yl)-carbamic acid ethyl ester (112671-58-6) → 5-azaindole (271-34-1)

Conditions	Yield
With sodium ethanolate In ethanol Heating; Yield given;

2-Hydroxy-2,3-dihydro-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester → 5-azaindole (271-34-1)

Conditions	Yield
With hydrogenchloride at 45 - 50℃; for 1h; Yield given;

3-methyl-4-nitropyridine N-oxide (1074-98-2) → 5-azaindole (271-34-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: dimethylformamide / 90 °C 2: H2 / Pd/C / ethanol / 60 °C View Scheme
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 20 - 90 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / ethanol / 4 h / 60 °C / 3750.38 Torr / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 1.5 h / 100 °C 2: palladium 10% on activated carbon; hydrogen / ethanol / 8 h / 20 - 65 °C / 1500.15 - 2250.23 Torr / Inert atmosphere; Autoclave View Scheme

N-(4-pyridyl) t-butyl carbamate (98400-69-2) → 5-azaindole (271-34-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) BuLi / 1.) THF, hexane, 0 deg C, 3 h, 2.) THF, hexane, 20 deg C, 1 h 2: 1.) t-BuLi / 1.) THF, pentane, -40 deg C, 1 h, 2.) THF, pentane, 20 deg C, 1 h 3: 5.5 M HCl / 1 h / 45 - 50 °C View Scheme

(3-methylpyridin-4-yl)carbamic acid tert-butyl ester (180253-65-0) → 5-azaindole (271-34-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) t-BuLi / 1.) THF, pentane, -40 deg C, 1 h, 2.) THF, pentane, 20 deg C, 1 h 2: 5.5 M HCl / 1 h / 45 - 50 °C View Scheme

3-bromopyridin-4-amine (13534-98-0) → 5-azaindole (271-34-1)

Conditions	Yield
Multi-step reaction with 3 steps 2: 93 percent / Pd(PPh3)2Cl2, Et4NCl / acetonitrile / 2.5 h / Heating 3: 90 percent / conc. HCl / methanol / 2 h / Heating View Scheme
Multi-step reaction with 3 steps 1: 52 percent / pyridine / 3 h / 0-10 deg C 2: CUI, Et3N / Pd(PPh3)2Cl2 / 100 - 110 °C 3: NaOEt / ethanol / Heating View Scheme
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / 5 - 20 °C / Inert atmosphere 2: bis-triphenylphosphine-palladium(II) chloride; tetrabutyl-ammonium chloride / acetonitrile / 2.5 h / Inert atmosphere; Reflux 3: hydrogenchloride / methanol; water / 5 h / Inert atmosphere; Reflux View Scheme

N-(3-bromopyridin-4-yl)acetamide (13535-03-0) → 5-azaindole (271-34-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 93 percent / Pd(PPh3)2Cl2, Et4NCl / acetonitrile / 2.5 h / Heating 2: 90 percent / conc. HCl / methanol / 2 h / Heating View Scheme
Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride; tetrabutyl-ammonium chloride / acetonitrile / 2.5 h / Inert atmosphere; Reflux 2: hydrogenchloride / methanol; water / 5 h / Inert atmosphere; Reflux View Scheme

3-Bromo-4-nitropyridine N-oxide (1678-49-5) → 5-azaindole (271-34-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: 75 percent / 20percent aq. TiCl3 / acetic acid / 25 h / Ambient temperature 3: 93 percent / Pd(PPh3)2Cl2, Et4NCl / acetonitrile / 2.5 h / Heating 4: 90 percent / conc. HCl / methanol / 2 h / Heating View Scheme

3-Methyl-4-nitropyridine (1678-53-1) → 5-azaindole (271-34-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 63 percent / dimethylformamide / 1 h / 90 °C 2: 91 percent / H2 / 10percent Pd/C / ethanol / 14.7 - 22.07 Torr / 1) 1 h, 20 deg C, 2) 3 h, 60 deg C View Scheme
Multi-step reaction with 3 steps 1: palladium; ethanol / Hydrogenation 2: THF 3: sodium anilide; sodium formate / 290 - 310 °C View Scheme

3-methyl-4-nitropyridine N-oxide (1074-98-2) + zinc → 5-azaindole (271-34-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 81 percent / PCl3 / 3.5 h / T < 0 deg C 2: 63 percent / dimethylformamide / 1 h / 90 °C 3: 91 percent / H2 / 10percent Pd/C / ethanol / 14.7 - 22.07 Torr / 1) 1 h, 20 deg C, 2) 3 h, 60 deg C View Scheme
Multi-step reaction with 2 steps 1: 92 percent / dimethylformamide / 2 h / 100 °C 2: 92 percent / H2 / Raney nickel / ethanol; H2O / 14.7 - 22.07 Torr / 1) 15 h, 20 deg C, 2) 3-5 h, 60 deg C View Scheme
Multi-step reaction with 2 steps 1: 96 percent / dimethylformamide / 1 h / 90 °C 2: 87 percent / H2 / 10percent Pd/C / ethanol / 14.7 - 22.07 Torr / 1) 1 h, 20 deg C, 2) 3 h, 60 deg C View Scheme

ethyl (3-bromopyridin-4-yl)carbamate (112671-56-4) → 5-azaindole (271-34-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: CUI, Et3N / Pd(PPh3)2Cl2 / 100 - 110 °C 2: NaOEt / ethanol / Heating View Scheme

1-benzyl-4,5-dihydro-4-oxopyrrolo<3,2-c>pyridine (26956-47-8) → 5-azaindole (271-34-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 79 percent / Na, liquid ammonia 2: 78 percent / phosphorus oxychloride / 5 h / 180 °C 3: 96 percent / H2 / 10percent Pd/C / ethanol View Scheme

4,5-dihydro-4-oxo-1H-pyrrolo<3,2-c>pyridine (54415-77-9) → 5-azaindole (271-34-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 78 percent / phosphorus oxychloride / 5 h / 180 °C 2: 96 percent / H2 / 10percent Pd/C / ethanol View Scheme

4-amino-3-methylpyridine (1990-90-5, 953018-16-1) → 5-azaindole (271-34-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: THF 2: sodium anilide; sodium formate / 290 - 310 °C View Scheme
Multi-step reaction with 3 steps 1: TiCl2(ClO4)2 / acetone / 1 h / 60 °C 2: salicylic acid; iron(II) oxide / N,N-dimethyl acetamide / 2 h / 70 °C 3: zinc(II) oxide / tetrachloromethane / 2 h / 90 °C View Scheme

{[(3-Trimethylsilanyl)ethynyl]-pyridin-4-yl}amine (765307-12-8) → 5-azaindole (271-34-1)

Conditions	Yield
With copper(I) iodide In N,N-dimethyl-formamide

3-methyl-4-nitropyridine N-oxide (1074-98-2) + N,N-dimethylformamide diethyl diacetal (1188-33-6) → 5-azaindole (271-34-1)

Conditions	Yield
With sodium hydroxide; ammonium formate; palladium In ethanol; water; N,N-dimethyl-formamide; toluene; benzene

5-azaindole (271-34-1) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl 1H-pyrrolo[3,2-c]pyridine-1-carboxylate (148760-75-2)

Conditions	Yield
With dmap In acetonitrile at 20℃; for 18h;	100%
With triethylamine In dichloromethane at 25℃; for 12h; Inert atmosphere;	98.2%
With triethylamine In dichloromethane at 25℃; for 12h; Inert atmosphere;	98.2%

5-azaindole (271-34-1) + benzyl chloroformate (501-53-1) → benzyl 1H-pyrrolo[3,2-c]pyridine-1-carboxylate (1426255-11-9)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 1h;	100%
With triethylamine In dichloromethane at 0 - 20℃; for 1h;	100%

5-azaindole (271-34-1) + 6-bromo-4-chloro-2-(2-fluoro-phenyl)-quinazoline (760947-12-4) → 6-bromo-2-(2-fluoro-phenyl)-4-pyrrolo[3,2-c]pyridin-1-yl-quinazoline (760946-13-2)

Conditions	Yield
With caesium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; for 1h;	98%

5-azaindole (271-34-1) → C7H5(2)HN2

Conditions	Yield
With water-d2; silver trifluoromethanesulfonate In chloroform-d1 at 90℃; for 18h; regioselective reaction;	97%

5-azaindole (271-34-1) + benzyl chloride (100-44-7) → N5-benzyl-5-azaindole

Conditions	Yield
In N,N-dimethyl-formamide at 140℃; for 6h;	96%

5-azaindole (271-34-1) + acetyl chloride (75-36-5) → 3-acetyl-5-azaindole

Conditions	Yield
With aluminium trichloride In dichloromethane at 20℃; Friedel-Crafts reaction;	94%

5-azaindole (271-34-1) + p-toluenesulfonyl chloride (98-59-9) → 1-tosyl-1H-pyrrolo[3,2-c]pyridine (1279863-30-7)

Conditions	Yield
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In water; toluene at 0 - 10℃; for 2h; Inert atmosphere;	93%
Stage #1: 5-azaindole With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 1.16667h; Inert atmosphere; Stage #2: p-toluenesulfonyl chloride In tetrahydrofuran for 15h;

5-azaindole (271-34-1) + benzoyl chloride (98-88-4) → 3-benzoyl-5-azaindole

Conditions	Yield
With aluminium trichloride In dichloromethane at 20℃; Friedel-Crafts reaction;	92%

5-azaindole (271-34-1) + 1,1,1-trifluoroacetophenone (434-45-7) → 2,2,2-trifluoro-1-phenyl-1-(1H-pyrrolo[3,2-c]pyridin-3-yl)ethan-1-ol

Conditions	Yield
With tetrabutyl phosphonium bromide; potassium carbonate In water at 20℃; for 12h; regioselective reaction;	92%

5-azaindole (271-34-1) → 3-iodo-1H-pyrrolo[3,2-c]pyridine (877060-47-4)

Conditions	Yield
With potassium hydroxide; iodine In N,N-dimethyl-formamide at 20℃; for 0.25h;	91%
With iodine; potassium hydroxide regiospecific reaction;	87%
Stage #1: 5-azaindole With potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: With iodine In N,N-dimethyl-formamide at 0 - 20℃; for 0.25h;	83%
With iodine; potassium hydroxide In N,N-dimethyl-formamide at 20℃;	73%
Stage #1: 5-azaindole With potassium hydroxide In N,N-dimethyl-formamide at 25℃; for 0.25h; Stage #2: With iodine In N,N-dimethyl-formamide at 25℃; for 0.25h;

5-azaindole (271-34-1) + 4-iodopyridine (15854-87-2) → 1-(pyridin-4-yl)-1H-pyrrolo[3,2-c]pyridine (1542750-10-6)

Conditions	Yield
With potassium phosphate In dimethyl sulfoxide at 80℃; for 5h; Ullmann-Goldberg Substitution; Inert atmosphere;	90%
With potassium phosphate; copper In dimethyl sulfoxide at 80℃; for 5h; Ullmann-Goldberg Substitution; Inert atmosphere;	90%

5-azaindole (271-34-1) + o-nitroiodobenzene (609-73-4) → 1-(2-nitrophenyl)-1H-pyrrolo[3,2-c]pyridine (1542750-13-9)

Conditions	Yield
With potassium phosphate; copper In dimethyl sulfoxide at 80℃; for 2h; Ullmann-Goldberg Substitution; Inert atmosphere;	89%
With potassium phosphate In dimethyl sulfoxide at 80℃; for 2h; Ullmann-Goldberg Substitution; Inert atmosphere;

5-azaindole (271-34-1) + ethyl 2-iodobenzoate (1829-28-3) → C16H14N2O2

Conditions	Yield
With copper(l) iodide; potassium carbonate; lithium chloride In N,N-dimethyl-formamide at 120℃; for 24h;	88%

5-azaindole (271-34-1) + Ethyl bromodifluoroacetate (667-27-6) → 1-(difluoromethyl)-1H-pyrrolo[3,2-c]pyridine

Conditions	Yield
With carbon dioxide; potassium hydroxide In acetonitrile at 130℃; for 12h; Autoclave;	88%

5-azaindole (271-34-1) + 1-Chloro-4-iodobenzene (637-87-6) → C13H9ClN2

Conditions	Yield
With copper(l) iodide; potassium carbonate; lithium chloride In N,N-dimethyl-formamide at 120℃; for 24h;	85%

5-azaindole (271-34-1) + methyl iodide (74-88-4) → 5-methyl-1H-pyrrolo[3,2-c]pyridin-5-ium iodide (1195996-58-7)

Conditions	Yield
In toluene at 120℃; for 2h; Inert atmosphere;	85%

5-azaindole (271-34-1) + p-Chlorothiophenol (106-54-7) → 3-((4-chlorophenyl)thio)-1H-pyrrolo[3,2-c]pyridine

Conditions	Yield
With caesium carbonate In dimethyl sulfoxide at 100℃; for 3h; Schlenk technique;	85%

5-azaindole (271-34-1) + 2-Iodobenzyl bromide (40400-13-3) → 1-(2-iodobenzyl)-1H-pyrrolo[3,2-c]pyridine

Conditions	Yield
Stage #1: 5-azaindole With potassium hydroxide In dimethyl sulfoxide at 20℃; for 0.5h; Schlenk technique; Stage #2: 2-Iodobenzyl bromide In dimethyl sulfoxide at 20℃; Schlenk technique;	85%

5-azaindole (271-34-1) + benzenesulfonyl chloride (98-09-9) → 1-Benzenesulfonyl-1H-pyrrolo<3,2-c>pyridine (109113-39-5)

Conditions	Yield
Stage #1: 5-azaindole With sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Stage #2: benzenesulfonyl chloride In tetrahydrofuran at 20℃;	84%
Stage #1: 5-azaindole With sodium hydride In mineral oil at 0℃; for 0.5h; Stage #2: benzenesulfonyl chloride at 0 - 20℃; for 1h;	69.4%
Stage #1: 5-azaindole With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Stage #2: benzenesulfonyl chloride In tetrahydrofuran at 0 - 20℃; for 1h;	69.4%

5-azaindole (271-34-1) + 2-mesitylenesulphonyl chloride (773-64-8) → 1-(2,4,6-trimethyl-benzenesulfonyl)-1H-pyrrolo[3,2-c]pyridine (1417718-51-4)

Conditions	Yield
With sodium hydride In tetrahydrofuran at 0 - 25℃; for 16h; Inert atmosphere;	84%
With sodium hydride at 0 - 20℃; for 16h;	84%

5-azaindole (271-34-1) + (5-methoxy-3-indolylmethyl)trimethylammonium iodide → 1-((5-methoxy-1H-indol-3-yl)methyl)-1H-pyrrolo[3,2-c]pyridine

Conditions	Yield
In water at 80℃; Sealed tube; Green chemistry; regioselective reaction;	84%

Upstream product

• 101870-39-7 N-(3-methyl-[4]pyridyl)-formamide 
• 141-53-7 sodium formate 
• 1865-45-8 sodium anilide 
• 13534-98-0 3-bromopyridin-4-amine 
• 765307-12-8 {[(3-Trimethylsilanyl)ethynyl]-pyridin-4-yl}amine 
• 104118-88-9 3-dimethylaminovinylene-4-nitropyridine-l-oxide 
• 19798-77-7 4-amino-3-chloropyridine 
• 74-86-2 acetylene 
• 271-29-4 6-azaindole 
• 98-59-9 p-toluenesulfonyl chloride 
• 800401-65-4 1H-pyrrolo [3,2-c] pyridine-2-carboxylic acid 
• 1990-90-5 4-amino-3-methylpyridine 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 108-99-6 3-Methylpyridine 

Downstream Products

• 148760-75-2 tert-butyl 1H-pyrrolo[3,2-c]pyridine-1-carboxylate 
• 60290-17-7 N₁-benzyl-5-azaindole 
• 109113-39-5 1-Benzenesulfonyl-1H-pyrrolo<3,2-c>pyridine 
• 23612-36-4 3-bromo-1H-pyrrolo[3,2-c]pyridine 
• 848410-13-9 tert-butyl (3aS,7aR)-2,3,3a,4,5,6,7,7a-octahydropyrrolo[3,2-c]pyridine-1-carboxylate 

Relevant articles and documents

A medicine intermediate 5 - aza indole synthesis method (by machine translation)

The present invention discloses a pharmaceutical intermediate 5 - aza indole synthesis method, comprises the following steps: the 3 - methyl - 4 - aminopyridine with acetone after mixing, heating to 40 - 60 °C, adding catalyst after adding the oxalate, under stirring conditions, refluxing reaction 1 - 2 h, filtering, the filtrate by reduced pressure distillation, recrystallization, prepared 4 - aminopyridine - 3 - pyruvate ester; in its entry into the DMA, adding salicylic acid then adding the FeO, heated to 60 - 70 °C, stirring reflux reaction for 2 - 3 h, filter, the filtrate is distilled under reduced pressure, to obtain 5 - aza indole - 2 - carboxylic acid; and after mixing with the carbon tetrachloride, heating to 70 - 90 °C, adding ZnO mixing, stirring reflux reaction for 2 - 3 h after, filtering, the filtrate is distilled under reduced pressure, to obtain 5 - azaindole. The application of the synthesis method is simple in operation, mild condition, less by-products, the product has high purity, product yield is relatively high. (by machine translation)

Preparation method of5-diazaindene

The invention discloses apreparation method of 5-diazaindene. 3-methyl-4-aminopyridine is evenly stirred and mixed with acetic anhydride and a catalyst for reaction, the obtained product is evenly mixed with pyrrolidine and DMF-DMA, reaction is performed at the temperature of 80-90 DEG Cunder the condition of the catalyst for 2-3 hours to obtain the final product 5-diazaindene. The method produces fewer by-products and is high in productpurity.In addition, the added novel catalyst makes reaction temperaturemore moderate, and reaction time is shortened greatly. In a word, the steps of the whole production process are simple, operation is easy, the cost of large-scale industrial production is low, and implementation is easy.

Design, synthesis and antiproliferative activity evaluation of new 5-azaisoindigo derivatives

New 5-azaisoindigo derivatives were synthesized with two key intermediates 5-azaoxindole (7) and substituted indole-2,3-dione (10) in this paper. Intermediate 7 was prepared from 3-methylpyridine (1) through 6 steps containing oxidation reaction and so on. Intermediate 10 was obtained by a convenient Sandmeyer's method. The target compounds 5-azaisoindigo derivatives 11a-f were obtained by condensation of these two intermediates 7 and 10 in acidic condition. All target compounds were evaluated for their antiproliferative activity against seven cell lines by SRB assay. Compounds 11e and 11f showed significant antiproliferative activity against K562 cells (IC50: 8.9 μM and 13.6 μM, respectively).