244-76-8

Basic information

• Product Name: alpha-carboline
• Synonyms: alpha-carboline;1-Azacarbazole;1H-Pyrido[2,3-b]indole;1-Hydro-9-dehydro-α-carboline;a-Carboline;9H-pyrido[2,3-b]indole;1,9-Diazafluorene 1-Azacarbazole;9H-1,9-Diazafluorene
• CAS NO: 244-76-8
• Molecular Formula: C₁₁H₈N₂
• Molecular Weight: 167.18668
• EINECS: 205-960-6
• Product Categories: Aromatics;Heterocycles;Indole Derivatives;Mutagenesis Research Chemicals
• Mol File: 244-76-8.mol
• Article Data: 46

Chemical Properties

• Melting Point: 210-212°C
• Boiling Point: 373℃
• Flash Point: 172℃
• Appearance: Light Brown Solid
• Density: 1.301
• Vapor Pressure: 1.99E-05mmHg at 25°C
• Refractive Index: 1.784
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility: Acetone, DMSO, Methanol (Slightly, Hetaed)
• PKA: 14.53±0.30(Predicted)
• CAS DataBase Reference: alpha-carboline(CAS DataBase Reference)
• NIST Chemistry Reference: alpha-carboline(244-76-8)
• EPA Substance Registry System: alpha-carboline(244-76-8)

Safety Data

• Hazardous Substances Data: 244-76-8(Hazardous Substances Data)

Usage

Chemical Properties

Light Brown Solid

Uses

A carcinogenic compound formed during cooking processes

InChI:InChI=1/C11H8N2/c1-2-6-10-8(4-1)9-5-3-7-12-11(9)13-10/h1-7H,(H,12,13)

Synthetic route

5,6,7,8-tetrahydro-9H-pyrido<2,3-b>indole (7076-11-1) → α-carboline (244-76-8)

Conditions	Yield
With palladium on activated carbon In diphenylether at 210℃; for 0.66h; Inert atmosphere;	97%
With palladium on activated charcoal; diphenylether; biphenyl

8-phenyltetrazolo[1,5-a]pyridine (1130816-42-0) → α-carboline (244-76-8)

Conditions	Yield
With silver hexafluoroantimonate; bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] In benzene at 130℃; for 24h; Solvent; Sealed tube; Glovebox; Inert atmosphere;	96%

3-bromo-N-phenylpyridine-2-amine (54904-02-8) → α-carboline (244-76-8)

Conditions	Yield
With palladium diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; tricyclohexylphosphine tetrafluoroborate In N,N-dimethyl acetamide; o-xylene at 145℃; for 16h; Inert atmosphere;	90%
With potassium tert-butylate; ammonia for 1h; Inert atmosphere; Irradiation;	88%
With palladium diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; CyJohnPhos In N,N-dimethyl acetamide at 140℃; for 1h; Inert atmosphere;	76%

3-chloro-N-phenyl-2-aminopyridine (6604-94-0) → α-carboline (244-76-8)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; 1,8-diazabicyclo[5.4.0]undec-7-ene In 1,4-dioxane at 180℃; for 0.166667h; Microwave irradiation; sealed tube;	88%
Stage #1: 3-chloro-N-phenyl-2-aminopyridine With palladium diacetate; triphenylphosphine In N,N-dimethyl-formamide for 0.166667h; Graebe-Ullmann Synthesis; Inert atmosphere; Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 130℃; for 48h; Graebe-Ullmann Synthesis; Inert atmosphere;	87%
With potassium tert-butylate; ammonia for 1h; Inert atmosphere; Irradiation;	75%

2,2-dimethyl-N-(2-(2-fluoro-3-pyridyl)phenyl)propanamide (146141-05-1) → α-carboline (244-76-8)

Conditions	Yield
With pyridine hydrochloride for 0.25h;	82%
With pyridine hydrochloride for 0.25h; Heating; cyclization of various o-pivaloylaminophenyl-o'-halopyridines;	82%

2,2-dimethyl-N-(2-(2-chloro-3-pyridyl)phenyl)propanamide (146141-06-2) → α-carboline (244-76-8)

Conditions	Yield
With pyridine hydrochloride for 0.25h;	82%

3-(2-nitro-phenyl)-pyridine (4253-80-9) → α-carboline (244-76-8)

Conditions	Yield
With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; triphenylphosphine In 1,4-dioxane at 55℃; for 96h; Cadogan-Cameron Wood Cyclization; Inert atmosphere; Irradiation;	81%
With 1,10-Phenanthroline; carbon monoxide; palladium diacetate In N,N-dimethyl-formamide at 140℃; under 3102.89 Torr; for 16h;	74%

malondialdehyde bis(diethyl acetal) (122-31-6) + 2-tosylamidoindole (36982-86-2) → α-carboline (244-76-8)

Conditions	Yield
With hydrogen bromide In ethanol at 80 - 100℃; for 1.5h;	76%

9-methoxymethyl-9H-pyrido[2,3-b]indole → α-carboline (244-76-8)

Conditions	Yield
With methanol; trifluorormethanesulfonic acid; trimethyl orthoformate In nitromethane at 100℃; for 1h;	74%

tert-butyl 3-((1E,3Z)-3-(methoxyimino)prop-1-en-1-yl)-1bH-indole-1-carboxylate (1497420-36-6) → α-carboline (244-76-8)

Conditions	Yield
In 1,2-dichloro-benzene at 240℃; for 3h; Sealed tube; Microwave irradiation;	73%

1-phenyl-1H-7-azabenzo[d][1,2,3]triazole (62052-02-2) → α-carboline (244-76-8)

Conditions	Yield
In 1,4-dioxane for 15h; Irradiation;	61%

2-(2-methanesulfonylanilino)-pyridine → benzo[4,5]imidazo[1,2-a]pyridine (245-47-6) + α-carboline (244-76-8)

Conditions	Yield
In tert-butyl alcohol for 4h; Cyclization; Irradiation;	A 3% B 59%

1-(pyridin-2-yl)-1H-benzo[d][1,2,3]triazole (13174-93-1) → α-carboline (244-76-8)

Conditions	Yield
With polyphosphoric acid at 160 - 175℃; for 3h;	47%
With PPA at 150 - 160℃; for 2h;	36%
With pyrophosphoric acid at 170℃; for 0.00833333h; microwave irradiation;	34%

3-(4-trifluoromethylphenyl)-1,2,3-triazolo<4,5-b>pyridine → α-carboline (244-76-8) + 2-aniline-3-hydroxypyridine (92755-42-5) + 1-azacarbazole-6-carboxylic acid + 3-hydroxy-2-anilinopyridine-4'-carboxylic acid

Conditions	Yield
With PPA at 140 - 180℃; for 0.5h;	A 1.4% B 10.6% C 25.4% D 42.5%

ethyl 4-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)benzoate → α-carboline (244-76-8) + 2-aniline-3-hydroxypyridine (92755-42-5) + 1-azacarbazole-6-carboxylic acid + 3-hydroxy-2-anilinopyridine-4'-carboxylic acid

Conditions	Yield
With PPA at 140 - 180℃; for 0.5h;	A 4% B 12.8% C 23.5% D 35%
With PPA at 140 - 180℃; for 0.5h;	A 4% B 12.8% C 23.5% D 35%
With PPA at 140 - 180℃; for 0.5h;	A 4% B 12.8% C 23.5% D 35%

2,3-dichloro-pyridine (2402-77-9) + aniline (62-53-3) → α-carboline (244-76-8)

Conditions	Yield
Stage #1: 2,3-dichloro-pyridine; aniline With palladium diacetate; triphenylphosphine; sodium t-butanolate In o-xylene at 120℃; for 3h; Inert atmosphere; Darkness; Stage #2: With tri-tert-butyl phosphine; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl acetamide; o-xylene at 150℃; for 12h; Inert atmosphere;	33%
Stage #1: 2,3-dichloro-pyridine; aniline With sodium t-butanolate; palladium diacetate; triphenylphosphine In o-xylene at 120℃; for 3h; Inert atmosphere; Stage #2: palladium diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; tricyclohexylphosphine In ISOPROPYLAMIDE; o-xylene at 150℃; for 12h;
Multi-step reaction with 2 steps 1.1: palladium diacetate; triphenylphosphine; sodium t-butanolate / toluene / 0.17 h / 20 Torr / Inert atmosphere 1.2: 16 h / 100 °C / Inert atmosphere 2.1: palladium diacetate; triphenylphosphine / N,N-dimethyl-formamide / 0.17 h / Inert atmosphere 2.2: 48 h / 130 °C / Inert atmosphere View Scheme

2-chloropyridine (109-09-1) + 2-Chloroaniline (95-51-2) → α-carboline (244-76-8)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium tert-butylate In 1,4-dioxane; 5,5-dimethyl-1,3-cyclohexadiene at 120℃; for 20h;	10%

3-(2-azidophenyl)pyridine (856849-78-0) + decalin (91-17-8) → γ-carboline (244-69-9) + α-carboline (244-76-8)

Conditions	Yield
at 180℃;

3-(2-azidophenyl)pyridine (856849-78-0) → γ-carboline (244-69-9) + α-carboline (244-76-8)

Conditions	Yield
With decalin at 180℃;

1-(N-L-triptophanyl)-1-deoxy-D-fructose (87251-66-9) → 5-hydroxymethyl-2-furfuraldehyde (67-47-0) + Maltol (118-71-8) + isomaltol (3420-59-5) + α-carboline (244-76-8) + L-Tryptophan (73-22-3)

Conditions	Yield
In water at 95℃; under 750.06 - 450036 Torr; Rate constant; Product distribution; various pressure; ΔV*;

1-benzylpyrazole (10199-67-4) + chloroform (67-66-3) → 2-chloropyrimidine (1722-12-9) + 2-phenylpyrimidine (7431-45-0) + α-carboline (244-76-8)

Conditions	Yield
at 550 - 555℃; Title compound not separated from byproducts;

chloroform (67-66-3) + 1-benzyl-4-chloro-1H-pyrazole (50877-40-2) → 2-phenylpyrimidine (7431-45-0) + 1-benzylpyrazole (10199-67-4) + α-carboline (244-76-8) + 3-chloro-9H-pyrido[2, 3-b]indole

Conditions	Yield
at 550 - 555℃; Further byproducts given. Title compound not separated from byproducts;

1-benzyl-4-chloro-1H-pyrazole (50877-40-2) → NH-pyrazole (288-13-1) + 1-benzylpyrazole (10199-67-4) + α-carboline (244-76-8) + 3-chloro-9H-pyrido[2, 3-b]indole

Conditions	Yield
With chloroform at 550 - 555℃; Further byproducts given. Title compound not separated from byproducts;

1--benztriazole → α-carboline (244-76-8)

Conditions	Yield
With zinc(II) chloride
With phosphoric acid

2-chloropyridine (109-09-1) → α-carboline (244-76-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 77 percent / 2 h / 150 - 160 °C 2: 36 percent / PPA / 2 h / 150 - 160 °C View Scheme
Multi-step reaction with 2 steps 1: 87 percent / 0.17 h / 180 °C / microwave irradiation 2: 34 percent / H4P2O7 / 0.01 h / 170 °C / microwave irradiation View Scheme

1,2,3-Benzotriazole (95-14-7) → α-carboline (244-76-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 77 percent / 2 h / 150 - 160 °C 2: 36 percent / PPA / 2 h / 150 - 160 °C View Scheme
Multi-step reaction with 2 steps 1: 5 percent / 0.17 h / 180 °C / microwave irradiation 2: 34 percent / H4P2O7 / 0.01 h / 170 °C / microwave irradiation View Scheme
Multi-step reaction with 2 steps 1: 30 percent / 0.17 h / 180 °C / microwave irradiation 2: 34 percent / H4P2O7 / 0.01 h / 170 °C / microwave irradiation View Scheme

2-bromo-pyridine (109-04-6) → α-carboline (244-76-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 30 percent / 0.17 h / 180 °C / microwave irradiation 2: 34 percent / H4P2O7 / 0.01 h / 170 °C / microwave irradiation View Scheme
Multi-step reaction with 2 steps 1: toluene / 18 h / Reflux 2: polyphosphoric acid / 3 h / 160 - 175 °C View Scheme
Multi-step reaction with 2 steps 1: toluene / Reflux 2: polyphosphoric acid / 160 - 175 °C View Scheme

2-methylsulfanyl-pyridine (18438-38-5) → α-carboline (244-76-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 5 percent / 0.17 h / 180 °C / microwave irradiation 2: 34 percent / H4P2O7 / 0.01 h / 170 °C / microwave irradiation View Scheme

2-Amino-3-bromopyridine (13534-99-1) → α-carboline (244-76-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / t-BuONa; 1,1'-bis(diphenylphosphino)ferrocine / Pd2(dba)3 / toluene / 17 h / 100 °C 2: 31 percent / Na2CO3 / Pd(OAc)2 / dimethylformamide / 67 h / Heating View Scheme
Multi-step reaction with 2 steps 1: palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate / tert-butyl alcohol 2: palladium diacetate; C26H35P; 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl acetamide View Scheme
Multi-step reaction with 2 steps 1: palladium diacetate; sodium t-butanolate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 2-methyl-propan-1-ol / 18 h / Reflux 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium diacetate; CyJohnPhos / N,N-dimethyl acetamide / 1 h / 140 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; palladium diacetate; sodium t-butanolate / toluene / 24 h / Reflux 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium diacetate; CyJohnPhos / N,N-dimethyl acetamide / 24 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; palladium diacetate; sodium t-butanolate / toluene / 24 h / Reflux 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium diacetate; CyJohnPhos / N,N-dimethyl acetamide / 24 h / Reflux View Scheme

2,6-diiodo-pyridine (53710-17-1) + α-carboline (244-76-8) → 9-(6-iodopyridin-2-yl)-9H-pyrido[2,3-b]indole

Conditions	Yield
With potassium phosphate; copper(l) iodide; trans-1,2-cyclohexanediamine In 1,4-dioxane for 12h; Reflux;	100%

α-carboline (244-76-8) + 1,3-dibromobenzene (108-36-1) → 9-(3-bromophenyl)-9H-pyrido[2,3-b]indole

Conditions	Yield
With potassium phosphate; copper(l) iodide; rac-diaminocyclohexane In toluene for 16h; Reflux;	94%
With copper(l) iodide; potassium carbonate In N,N-dimethyl-formamide for 24h; Inert atmosphere; Reflux;	68%
With potassium phosphate; copper(l) iodide; trans-1,2-Diaminocyclohexane In 1,4-dioxane for 36h; Reflux; Inert atmosphere;

2-bromo-pyridine (109-04-6) + α-carboline (244-76-8) → 9-(2-pyridyl)-9H-pyrido<2,3-b>indole

Conditions	Yield
With copper; potassium carbonate at 205℃; for 2h; Irradiation;	93%
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene for 4.5h; Inert atmosphere; Reflux;
Stage #1: 2-bromo-pyridine; α-carboline With palladium diacetate; sodium t-butanolate In toluene for 0.5h; Stage #2: With tri-tert-butyl phosphine In toluene for 4h; Reflux;

α-carboline (244-76-8) + iodobenzene (591-50-4) → 9-phenyl-9H-pyrido<2,3-b>indole

Conditions	Yield
With potassium phosphate; copper(l) iodide; rac-diaminocyclohexane In toluene for 16h; Reflux;	93%
With potassium phosphate; copper(l) iodide; (S,S)-1,2-diaminocyclohexane In 1,4-dioxane for 24h; Reflux;	70%
With copper; potassium carbonate at 200℃; for 5h; Irradiation;	59%
Inert atmosphere;

α-carboline (244-76-8) → 6-bromo-9H-pyrido[2,3-b]indole (26066-88-6)

Conditions	Yield
With N-Bromosuccinimide In dichloromethane at 20℃; Inert atmosphere;	93%
With bromine In dichloromethane at 20℃; for 1h;	91%
With N-Bromosuccinimide In dichloromethane at 20℃; for 2h;	89.7%

α-carboline (244-76-8) + 3,3’-oxybis(iodobenzene) (102391-48-0) → 9,9’-(oxybis(3,1-phenylene))bis(9H-pyrido[2,3-b]indole)

Conditions	Yield
With copper(I) oxide; 4,7-dimethoxy-1,10-phenanthroline; caesium carbonate In dimethyl sulfoxide at 130 - 160℃; Inert atmosphere;	92%

monomethyl oxalyl chloride (5781-53-3) + α-carboline (244-76-8) → C14H10N2O3

Conditions	Yield
With aluminium trichloride In dichloromethane at 20℃;	90%

α-carboline (244-76-8) + 2,7-dibromo-10-phenyl-10H-spiro[acridine-9,9'-fluorene] → 10-phenyl-2,7-bis(9H-pyrido[2,3-b]indol-9-yl)-10H-spiro[acridine-9,9'-fluorene]

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate In toluene at 110℃; for 10h; Buchwald-Hartwig Coupling; Inert atmosphere;	88.5%
With tris-(dibenzylideneacetone)dipalladium(0); tri tert-butylphosphoniumtetrafluoroborate In toluene; tert-butyl alcohol for 12h; Inert atmosphere; Reflux;	88.5%

2,6-dibromopyrazine (23229-25-6) + α-carboline (244-76-8) → C26H16N6

Conditions	Yield
With 1-methyl-1H-imidazole; copper(l) iodide; potassium carbonate In toluene at 120℃; for 16h; Sealed tube; Inert atmosphere;	87%

α-carboline (244-76-8) + but-3-enoic anhydride (1760-48-1) → C16H13NO

Conditions	Yield
With sulfuric acid In dichloromethane at 40℃; for 6h;	86%

α-carboline (244-76-8) → 6-iodo-9H-pyrido [2,3-b]indole (26066-89-7)

Conditions	Yield
Stage #1: α-carboline With acetic acid; potassium iodide for 1h; Reflux; Inert atmosphere; Stage #2: With potassium iodate for 2h; Reflux; Inert atmosphere;	85%

α-carboline (244-76-8) + 2-(2-bromophenyl)-5-phenyl-[1,3,4]oxadiazole (83817-43-0) → C25H16N4O

Conditions	Yield
With copper(l) iodide; potassium carbonate; L-proline In dimethyl sulfoxide at 90℃; for 48h; Inert atmosphere;	84.2%

α-carboline (244-76-8) + 1-{2-[4-(chloromethyl)phenoxy]ethyl}hexahydro-1H-azepine hydrochloride (223251-25-0) → 9-(4-(2-(azepan-1-yl)ethoxy)benzyl)-9H-pyrido[2,3-b]indole

Conditions	Yield
Stage #1: α-carboline With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h; Stage #2: 1-{2-[4-(chloromethyl)phenoxy]ethyl}hexahydro-1H-azepine hydrochloride In N,N-dimethyl-formamide at 20℃;	84%

α-carboline (244-76-8) + 1-(2-(4-(chloromethyl)phenoxy)ethyl)pyrrolidine hydrochloride → 9-(4-(2-(pyrrolidin-1-yl)ethoxy)benzyl)-9H-pyrido[2,3-b]indole

Conditions	Yield
Stage #1: α-carboline With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h; Stage #2: 1-(2-(4-(chloromethyl)phenoxy)ethyl)pyrrolidine hydrochloride In N,N-dimethyl-formamide at 20℃;	83%

α-carboline (244-76-8) + 4-fluoro-1-iodo-2-methylbenzene (66256-28-8) → C18H13FN2

Conditions	Yield
With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 7h; Temperature;	82.5%

α-carboline (244-76-8) → 6-nitro-9H-pyrido[2,3-b]indole (6453-22-1)

Conditions	Yield
With nitric acid In water at 0 - 30℃;	82%
With sulfuric acid; nitric acid In water at -5 - 0℃; for 0.333333h; Inert atmosphere;	78.2%
With sulfuric acid; nitric acid In water at -5 - 0℃; for 0.333333h; Inert atmosphere;	78.2%
With nitric acid
Multi-step reaction with 2 steps 1.1: ceric ammonium nitrate / acetonitrile / 12 h / Heating 1.2: 63 percent / DMAP / acetonitrile / 12 h / 20 °C 2.1: 79 percent / TFA / CH2Cl2 / 2 h / Heating View Scheme

α-carboline (244-76-8) + 2-bromo-4-phenylquinazoline → C25H16N4

Conditions	Yield
With potassium phosphate; copper(l) iodide; rac-diaminocyclohexane In N,N-dimethyl-formamide for 16h; Inert atmosphere; Reflux;	82%

α-carboline (244-76-8) + 4-(2-morpholin-1-yl-ethoxy)benzyl chloride hydrochloride → 4-(2-(4-((9H-pyridyl[2,3-b]indol-9-yl)methyl)phenoxy)ethyl)morpholine

Conditions	Yield
Stage #1: α-carboline With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h; Stage #2: 4-(2-morpholin-1-yl-ethoxy)benzyl chloride hydrochloride In N,N-dimethyl-formamide at 20℃;	82%

α-carboline (244-76-8) + 2,6-difluoro pyridine (1513-65-1) → 9-(6-(9H-indeno[2,1-b]pyridin-9-yl)pyridin-2-yl)-9H-pyrido[2,3-b]indole

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 150℃; for 12h; Inert atmosphere;	81%

1-bromo-3,5-dichloro-2,4,6-triazine (854450-65-0) + α-carboline (244-76-8) → C14H7Cl2N5

Conditions	Yield
Stage #1: α-carboline With sodium hydride In tetrahydrofuran; hexane at 20℃; for 1h; Inert atmosphere; Stage #2: 2-bromo-4,6-dichloro-1,3,5-triazine In tetrahydrofuran; hexane at 20℃; Inert atmosphere;	81%

α-carboline (244-76-8) + 2,8-dibromo-5H-5λ6-dibenzo[b,d]thiophene-5,5-dione (40307-15-1) → 2,8-bis(9H-pyrido[2,3-b]indol-9-yl)dibenzo[b,d]thiophene 5,5-dioxide

Conditions	Yield
With potassium phosphate; copper(l) iodide; trans-1,2-cyclohexanediamine In toluene for 12h; Inert atmosphere; Reflux;	80%

α-carboline (244-76-8) + 3,5-difluoropyridine-2-carbonitrile (298709-29-2) → C28H16N6

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 140℃; for 12h; Inert atmosphere;	80%

α-carboline (244-76-8) + 6-bromo-9H-pyrido[2,3-b]indole (26066-88-6) → C22H14N4

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In water; toluene for 6h; Inert atmosphere; Reflux;	78.9%

Upstream product

• 7076-11-1 5,6,7,8-tetrahydro-9H-pyrido<2,3-b>indole 
• 856849-78-0 3-(2-azidophenyl)pyridine 
• 91-17-8 decalin 
• 113975-22-7 2-fluoro-3-iodopyridine 
• 6604-94-0 3-chloro-N-phenyl-2-aminopyridine 
• 96424-68-9 2-bromo-3-chloropyridine 
• 504-29-0 2-aminopyridine 
• 694-80-4 2-bromo-1-chlorobenzene 
• 1692-25-7 3-pyridylboronic acid 
• 54230-88-5 8-bromotetrazolo[1,5-a]pyridine 
• 1130816-42-0 8-phenyltetrazolo[1,5-a]pyridine 
• 52200-48-3 3-bromo-2-chloropyridine 
• 62-53-3 aniline 
• 2402-77-9 2,3-dichloro-pyridine 

Downstream Products

• 79960-47-7 9-benzoyl-α-carboline 
• 1402414-65-6 9-(9-tosyl-carbazol-3-yl)-pyrido[2,3-b]indole 
• 1374147-31-5 9-(4-bromobenzene)-9H-pyridin[2,3-b]indole 

Relevant articles and documents

Synthesis of 6-substituted pyrido[2,3-b]indoles by electrophilic substitution

Regioselective electrophilic aromatic substitutions, acylation, bromination, and formylation, of unprotected pyrido[2,3-b]indole (α-carbolines) at the C-6 position are described. Alternative conditions for the nitration were investigated, which led to the unexpected appearance of the minor C-8 isomer. Georg Thieme Verlag Stuttgart.

Visible-light-driven Cadogan reaction

Visible-light-driven photochemical Cadogan-type cyclization has been discovered. The organic D-A type photosensitizer 4CzIPN found to be an efficient mediator to transfer energy from photons to the transient intermediate that breaks the barriers of deoxygenation in Cadogan reaction and enables a mild metal-free access to carbazoles and related heterocycles. DFT calculation results indicate mildly endergonic formation of the intermediate complex of nitrobiarenes and PPh3, which corresponds with experimental findings regarding reaction temperature. The robust synthetic capacity of the photoredox Cadogan reaction systems has been demonstrated by the viable productivity of a broad range of carbazoles and related N-heterocycles with good tolerance of various functionalities.

ORGANIC COMPOUNDS, LIGHE EMITTING DIODE AND LIGHT EMITTING DEVICE HAVING THE COMPOUNDS

The present invention relates to an organic compound having an amine core substituted with three aromatic rings, wherein a part of the three aromatic rings is substituted with a functional group capable of a solution process while the rest of the three aromatic rings is substituted with a hetero-aromatic functional group; and a light-emitting diode and a light-emitting device having the organic compound applied to a light-emitting layer. The organic compound may be used to the light-emitting layer to eliminate the HOMO energy barrier between the light-emitting layer and another light-emitting layer adjacent thereto. Also, the organic compound, when it forms a light-emitting layer in combination with light-emitting particles, may improve interfacial properties between the light-emitting layer and an adjacent layer to improve morphological properties of the light-emitting diode. The organic compound of the present invention, by allowing holes and electrons to be transported and implanted into a light emitting material layer in a balanced manner, may implement light-emitting diodes and light-emitting devices with improved luminance efficiency and capable of low-voltage driving.(110) First electrode(120) Second electrode(AA) Smooth interface morphology ↑COPYRIGHT KIPO 2019