3610-36-4

Basic information

• Product Name: 3-(2-Aminoethyl)-6-methoxyindole
• Synonyms: TIMTEC-BB SBB000286;AURORA KA-7732;2-(6-METHOXY-1H-INDOL-3-YL)-ETHYLAMINE;3-[2-AMINOETHYL]-6-METHOXYINDOLE;6-METHOXYTRYPTAMINE;2-(2-aminoethyl)-5-methoxyindole;6-METHOXYTRYPTAMINE Free base;6-METHOXYTRYPTAMINE 99%
• CAS NO: 3610-36-4
• Molecular Formula: C₁₁H₁₄N₂O
• Molecular Weight: 190.24
• EINECS: 222-778-2
• Product Categories: Tryptamines
• Mol File: 3610-36-4.mol
• Article Data: 9

Chemical Properties

• Melting Point: 146-147 °C(lit.)
• Boiling Point: 325.75°C (rough estimate)
• Flash Point: 183.636 °C
• Appearance: yellow/crystalline
• Density: 1.0815 (rough estimate)
• Vapor Pressure: 5.61E-06mmHg at 25°C
• Refractive Index: 1.5700 (estimate)
• Storage Temp.: 2-8°C
• PKA: 17.43±0.30(Predicted)
• Water Solubility: MODERATELY SOLUBLE
• CAS DataBase Reference: 3-(2-Aminoethyl)-6-methoxyindole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2-Aminoethyl)-6-methoxyindole(3610-36-4)
• EPA Substance Registry System: 3-(2-Aminoethyl)-6-methoxyindole(3610-36-4)

Safety Data

• Hazard Codes: C
• Statements: 43-34
• Safety Statements: 45-36/37/39-26
• WGK Germany: 3
• Hazardous Substances Data: 3610-36-4(Hazardous Substances Data)

Usage

Chemical Properties

off-white to beige crystalline powder

InChI:InChI=1/C11H14N2O/c1-14-9-2-3-10-8(4-5-12)7-13-11(10)6-9/h2-3,6-7,13H,4-5,12H2,1H3/p+1

Synthetic route

2-carboxyethyl-3-(2-phthalimidoethyl)-6-methoxyindole (282103-23-5) → 2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4)

Conditions	Yield
Stage #1: 2-carboxyethyl-3-(2-phthalimidoethyl)-6-methoxyindole With potassium hydroxide In water for 3h; Heating; Stage #2: With hydrogenchloride In water for 10h; Heating;	90%

C25H42N2O3Si → 2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4)

Conditions	Yield
Stage #1: C25H42N2O3Si With trifluoroacetic acid In dichloromethane at 20℃; for 1h; Inert atmosphere; Stage #2: With cesium fluoride In tetrahydrofuran; methanol; toluene at 20℃; for 6h; Inert atmosphere;	58%

2-(6-methoxy-1H-indol-3-yl)acetonitrile (23084-35-7) → 2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4)

Conditions	Yield
With methanol; ammonia; nickel under 73550.8 Torr; Hydrogenation;
With lithium aluminium tetrahydride; diethyl ether
With ethanol; sodium

2-(6-methoxy-1H-indol-3-yl)-2-oxo-acetamide (103858-66-8) → 2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4)

Conditions	Yield
With tetrahydrofuran; lithium aluminium tetrahydride

6-methoxytryptamine-2-carboxylic acid (20731-72-0) → 2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4)

Conditions	Yield
With hydrogenchloride

6-methoxy-3-(2-nitroethyl)-1H-indole (96096-61-6) → 2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol under 2585.7 Torr; for 12h;

6-methoxylindole (3189-13-7) → 2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 27 percent / tert-butylcatechol / xylene / 3 h / Heating 2: H2 / 10 percent Pd/C / ethanol / 12 h / 2585.7 Torr View Scheme
Multi-step reaction with 2 steps 1: methyl magnesium iodide; diethyl ether / Behandeln des Reaktionsgemisches mit Chloracetonitril 2: sodium; ethanol View Scheme
Multi-step reaction with 3 steps 1: acetic acid; dioxane 2: dimethyl sulfate; acetic acid; THF / Erwaermen des Reaktionsprodukts in H2O mit KCN 3: Raney nickel; NH3; methanol / 73550.8 Torr / Hydrogenation View Scheme
Multi-step reaction with 3 steps 1: diethyl ether 2: concentrated aqueous NH3 3: LiAlH4; THF View Scheme
Multi-step reaction with 2 steps 1.1: trichlorophosphate / 0.5 h / 0 °C / Inert atmosphere; Schlenk technique 1.2: 2 h / 20 °C / Inert atmosphere; Schlenk technique 2.1: ammonium acetate / 2 h / 115 °C / Inert atmosphere; Schlenk technique 2.2: 3 h / 0 - 65 °C / Inert atmosphere; Schlenk technique View Scheme

6-methoxy-3-((trimethyl-14-azaneyl)methyl)-1H-indole iodide (109507-20-2) → 2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4)

Conditions	Yield
Multi-step reaction with 2 steps 2: LiAlH4; diethyl ether View Scheme

1-(6-methoxy-1H-indol-3-yl)-N,N-dimethylmethanamine (62467-65-6) → 2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: dimethyl sulfate; acetic acid; THF / Erwaermen des Reaktionsprodukts in H2O mit KCN 2: Raney nickel; NH3; methanol / 73550.8 Torr / Hydrogenation View Scheme

7-methoxy-2,3,4,9-tetrahydro-1H-pyrido<3,4-b>indol-1-one (26579-69-1) → 2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: aq.-ethanolic KOH 2: aqueous HCl View Scheme

(6-methoxy-1H-indol-3-yl)(oxo)acetyl chloride (68104-22-3) → 2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: concentrated aqueous NH3 2: LiAlH4; THF View Scheme

2,β-Dinitro-4-methoxy-styrol (99459-34-4) → 2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: ethyl acetate; palladium/charcoal; ethanol / Hydrogenation.Reagens 4: Essigsaeure 2: diethyl ether 3: concentrated aqueous NH3 4: LiAlH4; THF View Scheme

6-methoxy-3-(2-nitrovinyl)indole (91138-34-0) → 2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃;

6-methoxylindole (3189-13-7) + 1-dimethylamino-2-nitroethene (73430-27-0, 87446-70-6, 1190-92-7) → 2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4)

Conditions	Yield
Stage #1: 6-methoxylindole; 1-dimethylamino-2-nitroethene In dichloromethane; trifluoroacetic acid at 20℃; for 2h; Stage #2: With lithium aluminium tetrahydride In tetrahydrofuran at -78℃;

6-methoxy-1H-indole-3-carbaldehyde (70555-46-3) + nitromethane (75-52-5) → 2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4)

Conditions	Yield
Stage #1: 6-methoxy-1H-indole-3-carbaldehyde; nitromethane With ammonium acetate at 115℃; for 2h; Henry Nitro Aldol Condensation; Inert atmosphere; Schlenk technique; Stage #2: With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 65℃; for 3h; Inert atmosphere; Schlenk technique;	270 mg

4-chlorobenzaldehyde (104-88-1) + 2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4) → C18H17ClN2O (1120500-26-6)

Conditions	Yield
With sodium sulfate In dichloromethane at 23℃; for 3h; Inert atmosphere; Sealed tube;	100%
With sodium sulfate In dichloromethane at 23℃; for 3h; Inert atmosphere;

4-cyanobenzaldehyde (105-07-7) + 2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4) → (E)-4-(((2-(6-methoxy-1H-indol-3-yl)ethyl)imino)methyl)benzonitrile

Conditions	Yield
With sodium sulfate In dichloromethane at 23℃; for 3h; Inert atmosphere; Sealed tube;	100%

4-formylbenzonitrile-α-d1 (109635-36-1) + 2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4) → (E)-4-(((2-(6-methoxy-1H-indol-3-yl)ethyl)imino)methyl-[2H])benzonitrile

Conditions	Yield
With sodium sulfate In dichloromethane at 23℃; for 3h; Inert atmosphere; Sealed tube;	100%

Glyoxilic acid (298-12-4) + 2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4) → 7-methoxy-2,3,4,9-tetrahydro-1H-β-carboline-1-carboxylic acid (108850-87-9)

Conditions	Yield
With potassium carbonate In water; ethyl acetate at 20℃; for 24h; pH=5; Pictet-Spengler Synthesis;	99%
With potassium hydroxide In water at 20℃; for 12h; pH=3 - 4; Pictet-Spengler reaction;
With NaOAc buffer In ethyl acetate for 48h; pH=4.5;

2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4) + Trifluoroacetaldehyde ethyl hemiacetal (433-27-2) → 7-methoxy-1-trifluoromethyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole (126260-60-4)

Conditions	Yield
at 110 - 120℃; for 5h;	98.4%
With hydrogenchloride In methanol at 20℃; Pictet-Spengler cyclisation;

1,1-dimethoxyethane (534-15-6) + 2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4) → 7-methoxy-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole hydrochloride (40959-16-8)

Conditions	Yield
Stage #1: 1,1-dimethoxyethane; 2-(6-methoxy-1H-indol-3-yl)ethanamine With trifluoroacetic acid In 1,2-dichloro-ethane at 110℃; for 0.05h; Pictet-Spengler Synthesis; Sealed tube; Microwave irradiation; Stage #2: With hydrogenchloride In ethyl acetate at 20℃;	98%

4-cyanobenzaldehyde (105-07-7) + 2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4) → (R)-4-(7-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)benzonitrile

Conditions	Yield
With (S)-N-benzyl-2-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido)-N,3-dimethylbutanamide; benzoic acid In toluene at 23℃; for 24h; Pictet-Spengler Synthesis; Inert atmosphere; Sealed tube; enantioselective reaction;	98%

3-pyridinecarboxaldehyde (500-22-1) + trifluoroacetic acid (76-05-1) + 2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4) → 1-(pyridin-3-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole trifluoroacetate

Conditions	Yield
In 1,2-dichloro-ethane at 110℃; for 0.0833333h; Pictet-Spengler Synthesis; Sealed tube; Microwave irradiation;	97%

di-tert-butyl dicarbonate (24424-99-5) + 2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4) → C16H22N2O3 (1159000-30-2)

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 12h;	96%

benzaldehyde (100-52-7) + 2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4) → 7-methoxy-1-phenyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole hydrochloride

Conditions	Yield
Stage #1: benzaldehyde; 2-(6-methoxy-1H-indol-3-yl)ethanamine With trifluoroacetic acid In 1,2-dichloro-ethane at 110℃; for 0.183333h; Pictet-Spengler Synthesis; Sealed tube; Microwave irradiation; Stage #2: With hydrogenchloride In ethyl acetate at 20℃;	95%

4-chlorobenzaldehyde (104-88-1) + 2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4) → (R)-1-(4-chlorophenyl)-7-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (1120500-34-6)

Conditions	Yield
With 1,1'-(2S,2'S)-1,1'-(4,10-dimethyl-1,4,7,10-tetraazacyclododecane-1,7-diyl)bis(3-methyl-1-oxobutane-2,1-diyl)bis(3-(3,5-bis(trifluoromethyl)phenyl)thiourea); 4-methoxybenzoic acid In toluene at 20℃; for 72h; Pictet-Spengler Synthesis; enantioselective reaction;	93%
With (S)-N-benzyl-2-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido)-N,3-dimethylbutanamide; benzoic acid In toluene at 23℃; for 66h; Pictet-Spengler cyclisation; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	78%

3,4,5-trimethoxybenzoylformic acid (88755-16-2) + 2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4) → N-(2-(6-methoxy-1H-indol-3-yl)ethyl)-2-(3,4,5-trimethoxyphenyl)-2-oxoacetamide

Conditions	Yield
With 1,1'-carbonyldiimidazole	93%

acetaldehyde (75-07-0) + 2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4) → tetrahydroharmine (486-93-1, 17019-01-1)

Conditions	Yield
With hydrogenchloride In water at 40℃; for 6h; Pictet-Spengler Synthesis;	92%
With sulfuric acid In water at 110℃; for 0.333333h;	63%
With sulfuric acid
Stage #1: 2-(6-methoxy-1H-indol-3-yl)ethanamine With hydrogenchloride In water at 30℃; Stage #2: acetaldehyde In water for 10h;
With acetic acid for 8h; Reflux;

isobutyraldehyde (78-84-2) + 2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4) → (R)-1-isopropyl-7-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (1120500-56-2)

Conditions	Yield
With (S)-N-benzyl-2-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido)-N,3-dimethylbutanamide In toluene at 23℃; for 88h; Pictet-Spengler cyclisation; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	90%

2-chloro-benzaldehyde (89-98-5) + 2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4) → (R)-1-(2-chlorophenyl)-7-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

Conditions	Yield
With 1,1'-(2S,2'S)-1,1'-(4,10-dimethyl-1,4,7,10-tetraazacyclododecane-1,7-diyl)bis(3-methyl-1-oxobutane-2,1-diyl)bis(3-(3,5-bis(trifluoromethyl)phenyl)thiourea); 4-methoxybenzoic acid In toluene at 20℃; for 72h; Pictet-Spengler Synthesis; enantioselective reaction;	89%

potassium cyanide (151-50-8) + (1S,2R,3R,5S,6S)-3-Hydroxy-2-methoxy-6-(2-oxo-ethyl)-5-(toluene-4-sulfonyloxymethyl)-cyclohexanecarboxylic acid methyl ester + 2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4) → (3S,4aR,5R,6S,7S,8aR)-3-Cyano-7-hydroxy-6-methoxy-2-[2-(6-methoxy-1H-indol-3-yl)-ethyl]-decahydro-isoquinoline-5-carboxylic acid methyl ester

Conditions	Yield
With magnesium sulfate In acetonitrile for 1h; Strecker reaction;	87%

m-bromobenzoic aldehyde (3132-99-8) + 2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4) → (R)-1-(3-bromophenyl)-7-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (1120500-41-5)

Conditions	Yield
With (S)-N-benzyl-2-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido)-N,3-dimethylbutanamide; benzoic acid In toluene at 23℃; for 19h; Pictet-Spengler cyclisation; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	87%
With 1,1'-(2S,2'S)-1,1'-(4,10-dimethyl-1,4,7,10-tetraazacyclododecane-1,7-diyl)bis(3-methyl-1-oxobutane-2,1-diyl)bis(3-(3,5-bis(trifluoromethyl)phenyl)thiourea); 4-methoxybenzoic acid In toluene at 20℃; for 72h; Pictet-Spengler Synthesis; enantioselective reaction;	84%

benzaldehyde (100-52-7) + 2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4) → 7-methoxy-1-phenyl-2,3,4,9-tetrahydro-1H-β-carboline (865681-22-7)

Conditions	Yield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 110℃; for 0.166667h; Microwave irradiation; Sealed tube;	87%

potassium cyanide + C28H32O9S + 2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4) → C34H39N3O6

Conditions	Yield
With magnesium sulfate In acetonitrile diastereoselective reaction;	87%

4-Nitrobenzenesulfonyl chloride (98-74-8) + 2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4) → N-(2-(6-methoxy-1H-indol-3-yl)ethyl)-4-nitrobenzenesulfonamide

Conditions	Yield
With triethylamine In dichloromethane at 20 - 30℃; for 2h; Inert atmosphere;	87%

acetic anhydride (108-24-7) + 2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4) → N-(2-(6-methoxy-1H-indol-3-yl)ethyl)acetamide (22375-73-1)

Conditions	Yield
With TEA In tetrahydrofuran for 6h; Ambient temperature;	86%

2-Ethylbutyraldehyde (97-96-1) + 2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4) → (R)-7-methoxy-1-(pentan-3-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (1120500-58-4)

Conditions	Yield
With (S)-N-benzyl-2-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido)-N,3-dimethylbutanamide In toluene at 23℃; for 120h; Pictet-Spengler cyclisation; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	84%

4-bromo-benzaldehyde (1122-91-4) + 2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4) → (R)-1-(4-bromophenyl)-7-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (1120500-38-0)

Conditions	Yield
With 1,1'-(2S,2'S)-1,1'-(4,10-dimethyl-1,4,7,10-tetraazacyclododecane-1,7-diyl)bis(3-methyl-1-oxobutane-2,1-diyl)bis(3-(3,5-bis(trifluoromethyl)phenyl)thiourea); 4-methoxybenzoic acid In toluene at 20℃; for 72h; Pictet-Spengler Synthesis; enantioselective reaction;	84%
With (S)-N-benzyl-2-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido)-N,3-dimethylbutanamide; benzoic acid In toluene at 23℃; for 74h; Pictet-Spengler cyclisation; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	79%

2-(isocyanatomethyl)-1,3-dioxolane (1467040-44-3) + 2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4) → 9-methoxy-5,6,11,11b-tetrahydro-1H-imidazo[1',5':1,2]pyrido[3,4-b]indol-3(2H)-one (1467040-48-7)

Conditions	Yield
Stage #1: 2-(isocyanatomethyl)-1,3-dioxolane; 2-(6-methoxy-1H-indol-3-yl)ethanamine In tetrahydrofuran at 20℃; for 7h; Pictet-Spengler Synthesis; Inert atmosphere; Stage #2: With hydrogenchloride In methanol; water at 55℃; for 4h; Pictet-Spengler Synthesis; Inert atmosphere;	84%

N-(4-carboxybenzyl)-1-(3-chlorophenyl)-N-methylmethanaminium chloride (1605289-54-0) + 2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4) → 4-{[(3-chlorobenzyl)(methyl)amino]methyl}-N-[2-(6-methoxy-1H-indol-3-yl)ethyl]benzamide (1317668-18-0)

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 20℃;	82%

isobutyraldehyde (78-84-2) + 2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4) → 1-isopropyl-7-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole hydrochloride

Conditions	Yield
Stage #1: isobutyraldehyde; 2-(6-methoxy-1H-indol-3-yl)ethanamine With trifluoroacetic acid In 1,2-dichloro-ethane at 110℃; for 0.05h; Pictet-Spengler Synthesis; Sealed tube; Microwave irradiation; Stage #2: With hydrogenchloride In ethyl acetate at 20℃;	82%

isobutyraldehyde (78-84-2) + trifluoroacetic acid (76-05-1) + 2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4) → 1-isopropyl-7-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole hydrochloride

Conditions	Yield
In 1,2-dichloro-ethane at 110℃; for 0.05h; Pictet-Spengler Synthesis; Sealed tube; Microwave irradiation;	82%

4-fluorobenzaldehyde (459-57-4) + 2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4) → (R)-1-(4-fluorophenyl)-7-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (1120500-35-7)

Conditions	Yield
With (S)-N-benzyl-2-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido)-N,3-dimethylbutanamide; benzoic acid In toluene at 23℃; for 70h; Pictet-Spengler cyclisation; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	81%

10-methoxy-2,2-dimethyl-2,6,7,12-tetrahydroindolo[2,3-a]quinolizin-4(3H)-one + 2-(6-methoxy-1H-indol-3-yl)ethanamine (3610-36-4) → (+)-peganumine A (1620517-85-2)

Conditions	Yield
With (R)-2,6-bis(3,5-difluoro-4-(trifluoromethyl)phenyl)-4H-dinaphtho[2,1-d:1',2'-f][1,3,2]dithiazepine 3,3,5,5-tetraoxide In toluene at 60℃; Catalytic behavior; Solvent; Temperature; Pictet-Spengler Synthesis; Inert atmosphere; Schlenk technique; Molecular sieve; Sealed tube; enantioselective reaction;	81%

Upstream product

• 91138-34-0 6-methoxy-3-(2-nitrovinyl)indole 
• 70555-46-3 6-methoxy-1H-indole-3-carbaldehyde 
• 75-52-5 nitromethane 
• 3189-13-7 6-methoxylindole 
• 73430-27-0 1-dimethylamino-2-nitroethene 
• 99459-34-4 2,β-Dinitro-4-methoxy-styrol 
• 68104-22-3 (6-methoxy-1H-indol-3-yl)(oxo)acetyl chloride 
• 26579-69-1 7-methoxy-2,3,4,9-tetrahydro-1H-pyrido<3,4-b>indol-1-one 
• 62467-65-6 1-(6-methoxy-1H-indol-3-yl)-N,N-dimethylmethanamine 
• 109507-20-2 6-methoxy-3-((trimethyl-14-azaneyl)methyl)-1H-indole iodide 
• 282103-23-5 2-carboxyethyl-3-(2-phthalimidoethyl)-6-methoxyindole 
• 96096-61-6 6-methoxy-3-(2-nitroethyl)-1H-indole 
• 20731-72-0 6-methoxytryptamine-2-carboxylic acid 
• 103858-66-8 2-(6-methoxy-1H-indol-3-yl)-2-oxo-acetamide 

Downstream Products

• 881204-74-6 C₁₉H₂₁N₃O₄ 
• 91566-22-2 7-methoxy-1,2,3,4-tetrahydro-β-carboline 
• 1120500-35-7 (R)-1-(4-fluorophenyl)-7-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole 
• 62230-10-8 1-acetyl-7-methoxy-9H-β-carboline 
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Relevant articles and documents

Practical and phase transfer-catalyzed synthesis of 6-methoxytryptamine

A convenient and cost-effective synthesis of 6-methoxytryptamine (1), starting from commercially available phthalimide and 1-bromo-3-chloropropane via PTC N-alkylation, PTC C-alkylation, Japp-Klingemann reaction, hydrolysis, and decarboxylation, has been accomplished with a 44% overall yield. Copyright Taylor & Francis Group, LLC.

1-BENZYLSPIRO[PIPERIDINE-4,1′-PYRIDO[3,4-b]indole] ‘co-potentiators’ for minimal function CFTR mutants

We previously identified a spiro [piperidine-4,1-pyrido [3,4-b]indole] class of co-potentiators that function in synergy with existing CFTR potentiators such as VX-770 or GLGP1837 to restore channel activity of a defined subset of minimal function cystic fibrosis transmembrane conductance regulator (CFTR) mutants. Here, structure-activity studies were conducted to improve their potency over the previously identified compound, 20 (originally termed CP-A01). Targeted synthesis of 37 spiro [piperidine-4,1-pyrido [3,4-b]indoles] was generally accomplished using versatile two or three step reaction protocols with each step having high efficiency. Structure-activity relationship studies established that analog 2i, with 6′-methoxyindole and 2,4,5-trifluorobenzyl substituents, had the greatest potency for activation of N1303K-CFTR, with EC50 ～600 nM representing an ～17-fold improvement over the original compound identified in a small molecule screen.

A Desymmetrization-Based Total Synthesis of Reserpine

Reported herein is a desymmetrization-based synthetic approach to the fused polycyclic indole alkaloid reserpine. The centerpiece of the developed strategy features an internal desymmetrization process that enabled the use of a readily accessible and nonstereogenic reserpine E-ring precursor, in contrast to the synthesis-intensive and stereodefined E-ring intermediates employed in all past reserpine syntheses. Utilization of inexpensive reagents through an orchestrated sequence of carefully selected chemical transformations further highlight the overall effectiveness of the developed pathway.