526-55-6

Basic information

• Product Name: Tryptophol
• Synonyms: INDOLE-3-ETHANOL;B-3-INDOLEETHANOL;B-3-INDOLYLETHANOL;BETA-3-INDOLYLETHANOL;3-(BETA-HYDROXYETHYL)INDOLE;3-INDOLEETHANOL;2-(1H-INDOL-3-YL)ETHAN-1-OL;2-(1H-INDOL-3-YL)-ETHANOL
• CAS NO: 526-55-6
• Molecular Formula: C₁₀H₁₁NO
• Molecular Weight: 161.2
• EINECS: 208-393-2
• Product Categories: Heterocyclic Compounds;Indoles;Simple Indoles
• Mol File: 526-55-6.mol
• Article Data: 79

Chemical Properties

• Melting Point: 56-59 °C(lit.)
• Boiling Point: 174 °C (2.02527 mmHg)
• Flash Point: 255 °C
• Appearance: Off-white to brown/Crystalline Mass, Crystals, Flakes or Powder
• Density: 1.0840 (rough estimate)
• Vapor Pressure: 9.66E-06mmHg at 25°C
• Refractive Index: 1.5200 (estimate)
• Storage Temp.: 2-8°C
• Solubility: methanol: 0.1 g/mL, clear
• PKA: 15.16±0.10(Predicted)
• Water Solubility: 10 g/L (20 ºC)
• Merck: 14,9798
• BRN: 125553
• CAS DataBase Reference: Tryptophol(CAS DataBase Reference)
• NIST Chemistry Reference: Tryptophol(526-55-6)
• EPA Substance Registry System: Tryptophol(526-55-6)

Safety Data

• Hazard Codes: Xi
• Statements: 24/25:
• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: KL3685000
• F: 8
• TSCA: Yes
• Hazardous Substances Data: 526-55-6(Hazardous Substances Data)

Usage

Chemical Properties

off-white to brown crystalline mass, crystals,

Uses

Different sources of media describe the Uses of 526-55-6 differently. You can refer to the following data:
1. Tryptophol is a metabolite formed in the liver after disulfiram treatment that induces sleep in humans. It is also a secondary product of alcoholic fermentation.
2. Reactant for preparation of:Inhibitors of the C-terminal domain of RNA polymerase II and their antitumor activitiesAnti-HIV-1 agentsInhibitors of Protein-Protein InteractionsPartial agonists of the serotonin 5-HT1A receptorGrowth hormone secretagoguesVascular endothelial growth factor (VEGF) inhibitorsA2B adenosine receptor ligandsPotential detoxification inhibitors of the crucifer phytoalexin brassininInhibitors of interleukine 6Dual binding site acetylcholinesterase inhibitors

Definition

ChEBI: An indolyl alcohol that is ethanol substituted by a 1H-indol-3-yl group at position 2.

Synthesis Reference(s)

Canadian Journal of Chemistry, 42, p. 485, 1964 DOI: 10.1139/v64-070

Purification Methods

Crystallise it from diethyl ether/pet ether, *C6H6, *C6H6/pet ether. The picrate has m 100-101o (from *C6H6). [Beilstein 21 I 218, 21 II 49, 21 III/IV 788, 21/3 V 61.]

InChI:InChI=1/C10H11NO/c12-6-5-8-7-11-10-4-2-1-3-9(8)10/h1-4,7,11-12H,5-6H2

Synthetic route

indole-3-acetic acid (87-51-4) → 2-(3-indole)-ethanol (526-55-6)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 3h; Reflux;	100%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 10h; Inert atmosphere;	96%
Stage #1: indole-3-acetic acid With 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane at 20℃; for 12h; Inert atmosphere; Stage #2: With silica gel In methanol at 50℃; for 3h;	92%

2-(3-indolyl)oxoacetic acid methyl ester (18372-22-0) → 2-(3-indole)-ethanol (526-55-6)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 12h;	100%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 70℃; for 5h; Inert atmosphere;	80%
With sodium borohydrid In isopropyl alcohol

3-(2-((tert-butyldimethylsilyl)oxy)ethyl)-1H-indole (101079-48-5) → 2-(3-indole)-ethanol (526-55-6)

Conditions	Yield
With aluminium(III) chloride hexahydrate In methanol at 100℃; for 0.25h; Solvent; Temperature; Microwave irradiation; Sealed tube; chemoselective reaction;	98%
With cerium (IV) sulfate tetrahydrate In methanol at 130℃; for 0.333333h; Microwave irradiation;	90%

Indole-3-acetic acid methyl ester (1912-33-0) → 2-(3-indole)-ethanol (526-55-6)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran	96%
With isopropyl alcohol In hexane at 0 - 20℃; for 0.583333h; Bouveault-Blanc Reduction; Inert atmosphere;	81%
With tetrabutylammonium borohydride In dichloromethane for 10h; Heating;	69%

ethyl 3-indoleacetate (778-82-5) → 2-(3-indole)-ethanol (526-55-6)

Conditions	Yield
With methanol; Na/SiO2 In tetrahydrofuran at 0 - 25℃; Bouveault-Blanc reduction; Inert atmosphere;	95%
With samarium diiodide; water; triethylamine In tetrahydrofuran at 20℃; for 20h; Inert atmosphere;	81%
Stage #1: ethyl 3-indoleacetate With polyethylsiloxane; LiTi(OPr-i)4 at 100℃; for 24h; Stage #2: With sodium hydroxide In tetrahydrofuran for 3h; Heating;	49%
With lithium aluminium tetrahydride; diethyl ether
With samarium diiodide; water; triethylamine In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;	99 %Spectr.

2,3-dihydro-2H-furan (1191-99-7) + phenylhydrazine hydrochloride (59-88-1) → 2-(3-indole)-ethanol (526-55-6)

Conditions	Yield
With sulfuric acid In N,N-dimethyl acetamide; water at 100℃;	92%
With L-(+)-tartaric acid-urea melt at 70℃; for 1h; Fischer Indole Synthesis;	90%
With montmorillonite K-10 In N,N-dimethyl acetamide; water at 80℃; for 2h;	75%

1-triethylsilanyl-4-(triethylsilanyloxy)but-1-yne (160194-28-5) + 2-bromoaniline (615-36-1) → 2-(3-indole)-ethanol (526-55-6)

Conditions	Yield
Stage #1: 1-triethylsilanyl-4-(triethylsilanyloxy)but-1-yne; 2-bromoaniline With 2 mol% Pd/C; sodium carbonate In N,N-dimethyl-formamide at 120℃; for 18h; Larock heteroannulation; Inert atmosphere; Stage #2: With hydrogenchloride In water regioselective reaction;	87%

2,3-dihydro-1H-indole-3-ethanol (40118-09-0) → 2-(3-indole)-ethanol (526-55-6)

Conditions	Yield
With dichloro[1,3-bis(2-methylphenyl)-2-imidazolidinylidene](benzylidene) (tricyclohexylphosphine) ruthenium(II); oxygen In ethyl acetate at 70℃; under 760.051 Torr; for 46h; Sealed tube;	85%

3-indolylacetamide (879-37-8) → 2-(3-indole)-ethanol (526-55-6)

Conditions	Yield
With samarium diiodide; water; triethylamine In tetrahydrofuran at 23℃; for 18h; Inert atmosphere; chemoselective reaction;	82%
Multi-step reaction with 2 steps 1: aqueous NaOH 2: lithium alanate; diethyl ether View Scheme

carbon monoxide (201230-82-2) + 2-[3-(tetrahydro-2H-pyran-2-yloxy)prop-1-yn-1-yl]aniline (287477-27-4) → acetic acid 2-(1H-indol-3-yl)ethyl ester (13137-14-9) + 2-(3-indole)-ethanol (526-55-6) + 3-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-1H-indole (156049-44-4)

Conditions	Yield
With carbonylhydridetris(triphenylphosphine)rhodium(I); hydrogen; 1,2-bis-(diphenylphosphino)ethane In toluene at 100℃; under 18751.9 Torr; for 8h; regioselective reaction;	A n/a B n/a C 78%

carbon monoxide (201230-82-2) + (E)-3-(2-aminophenyl)prop-2-en-1-ol (195191-58-3) → 2-(3-indole)-ethanol (526-55-6)

Conditions	Yield
With carbonylhydridetris(triphenylphosphine)rhodium(I); hydrogen; triphenylphosphine In toluene at 70℃; under 15514.4 Torr; for 70h;	73%

tryptamine (61-54-1) → 2-(3-indole)-ethanol (526-55-6)

Conditions	Yield
With carbonylchloro[4,5-bis(diisopropylphosphinomethyl)acridine]hydridoruthenium(II); water In 1,4-dioxane at 135℃; for 48h; Pressure; Schlenk technique; Inert atmosphere;	62%

2,2-dimethyl-propionic acid 2-(1H-indol-3-yl)-ethyl ester → 2-(3-indole)-ethanol (526-55-6)

Conditions	Yield
With polymer-supported potassium thiophenolate In tetrahydrofuran; ethylene glycol at 140℃;	50%

3-(2-(allyloxy)ethyl)-1-methyl-1H-indole → 2-(3-indole)-ethanol (526-55-6) + 3-(2-(allyloxy)ethyl)-1H-indole

Conditions	Yield
With ammonia; sodium In tetrahydrofuran at -78 - -50℃; for 4h;	A 22% B 50%

methanol (67-56-1) + 2-(Indol-3'-yl)ethyl Trichloroacetate (141972-15-8) → 2-(3-indole)-ethanol (526-55-6) + 1,3,4,7-tetrahydro-7,7-dimethoxyoxocino<4,5,6-cd>indol-6-one (141972-21-6)

Conditions	Yield
With acetonitrile for 0.416667h; Irradiation;	A 48% B 42%

3-phenylpropanoic acid methyl ester (103-25-3) + indole-2,3-dione (91-56-5) + lithium diisopropyl amide (4111-54-0) → 2-(3-indole)-ethanol (526-55-6) + β-(phenylmethyl)-1H-indole-ethanol (178665-43-5)

Conditions	Yield
In tetrahydrofuran; cyclohexane; water; 3-Phenylpropionic acid	A 46.9% B n/a

2,3-dihydro-2H-furan (1191-99-7) + phenylhydrazine (100-63-0) → 2-(3-indole)-ethanol (526-55-6)

Conditions	Yield
With acetic acid In water Reflux;	46%

S-methyl tryptophol dithiocarbonate → 2-(3-indole)-ethanol (526-55-6)

Conditions	Yield
With Leptosphaeria maculans In acetonitrile for 24h; Enzymatic reaction;	32%

2-(1H-indol-3-yl)-N,N-dimethylacetamide (91566-04-0) → 2-(3-indole)-ethanol (526-55-6)

Conditions	Yield
With ethanol; sodium In hexane; paraffin oil at 0℃; for 0.0833333h;	32%

2-ethoxytetrahydrofuran (13436-46-9) + phenylhydrazine hydrochloride (59-88-1) → 2-(3-indole)-ethanol (526-55-6)

Conditions	Yield
In ethanol Heating;	21.5%

indole (120-72-9) + 2-acetylaminoethanol (142-26-7) → 2-(3-indole)-ethanol (526-55-6) + N-Acetyltryptamine (1016-47-3) + N-(2,2-bis(1H-indol-3-yl)ethyl)acetamide

Conditions	Yield
With dichloro(pentamethylcyclopentadienyl) iridium; potassium acetate at 150℃; for 48h; Reagent/catalyst; Inert atmosphere; Sealed tube;	A 10% B 12% C 21%

carbon monoxide (201230-82-2) + allyl alcohol (107-18-6) + phenylhydrazine (100-63-0) → 2-(3-indole)-ethanol (526-55-6)

Conditions	Yield
With hydrogen; toluene-4-sulfonic acid; 6,6′-[(3,3′-di-tert-butyl-5,5′-dimethoxy-1,1′-biphenyl-2,2′-diyl)bis(oxy)]bis(di-benzo[d,f][1,3,2]dioxaphosphepin); acetylacetonatodicarbonylrhodium(l) In 1,4-dioxane at 60 - 100℃; under 15001.2 Torr; for 43h;	17%

2-(1-Triisopropylsilanyl-1H-indol-3-yl)-ethanol (181780-88-1) → 2-(3-indole)-ethanol (526-55-6)

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 25℃; for 0.166667h; Yield given;

4-(trimethylsilyl)but-3-yn-1-ol (2117-12-6) + 2-iodophenylamine (615-43-0) → 2-(3-indole)-ethanol (526-55-6) + trifluoro-acetic acid 2-(1H-indol-3-yl)-ethyl ester

Conditions	Yield
Yield given; Multistep reaction;

trifluoro-acetic acid 2-(1H-indol-3-yl)-ethyl ester → 2-(3-indole)-ethanol (526-55-6)

Conditions	Yield
With sodium methylate In methanol

oxirane (75-21-8) + indolyl magnesium bromide → 2-(3-indole)-ethanol (526-55-6)

Conditions	Yield
With diethyl ether; benzene und folgenden Erhitzen des Reaktionsgemisches auf ca. 100grad nach Abdestillieren des Aethers.;

indole (120-72-9) + fluorobenzene*Cr(CO)3 complex → 2-(3-indole)-ethanol (526-55-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: diethyl ether 2: diethyl ether / 12 h / 20 °C 3: 100 percent / LiAlH4 / tetrahydrofuran / 12 h / 20 °C View Scheme

indolyl-3-glyoxylyl chloride (22980-09-2) → 2-(3-indole)-ethanol (526-55-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: diethyl ether / 12 h / 20 °C 2: 100 percent / LiAlH4 / tetrahydrofuran / 12 h / 20 °C View Scheme
With sodium borohydrid In diethylene glycol dimethyl ether
Multi-step reaction with 2 steps 1: diethyl ether / 0 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: triethylamine / 0.5 h / Reflux; Inert atmosphere 2: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere; Reflux View Scheme
Multi-step reaction with 2 steps 1: diethyl ether / 0 °C / Inert atmosphere 2: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 80 °C / Inert atmosphere View Scheme

2-iodophenylamine (615-43-0) → 2-(3-indole)-ethanol (526-55-6)

Conditions	Yield
Multi-step reaction with 2 steps 2: NaOMe / methanol View Scheme
Multi-step reaction with 2 steps 2: NaOMe / methanol View Scheme

dichloroacethyl chloride (79-36-7) + 2-(3-indole)-ethanol (526-55-6) → 2-(Indol-3'-yl)ethyl Dichloroacetate (141972-14-7)

Conditions	Yield
With pyridine In dichloromethane for 18h; kept in the dark;	100%

2-(3-indole)-ethanol (526-55-6) + acetic anhydride (108-24-7) → acetic acid 2-(1H-indol-3-yl)ethyl ester (13137-14-9)

Conditions	Yield
With pyridine; dmap In dichloromethane for 24h; Ambient temperature;	100%
With pyridine at 20℃; for 15h; Inert atmosphere;	99%
With pyridine for 1h; Ambient temperature;	55.3 g
With pyridine at 20℃; for 15h; Inert atmosphere;

2-(3-indole)-ethanol (526-55-6) + tert-butyldimethylsilyl chloride (18162-48-6) → 3-(2-((tert-butyldimethylsilyl)oxy)ethyl)-1H-indole (101079-48-5)

Conditions	Yield
With 1H-imidazole In tetrahydrofuran at 0 - 20℃; for 0.5h; Inert atmosphere;	100%
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h;	100%
With 1H-imidazole In N,N-dimethyl-formamide for 16h; Ambient temperature;	99%

2-(3-indole)-ethanol (526-55-6) + triisopropylsilyl chloride (13154-24-0) → 3-(2-((triisopropylsilyl)oxy)ethyl)-1H-indole (242806-12-8)

Conditions	Yield
With 1H-imidazole In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;	100%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; Substitution;	99%

2-(3-indole)-ethanol (526-55-6) → 2,3-dihydro-1H-indole-3-ethanol (40118-09-0)

Conditions	Yield
With sodium cyanoborohydride; acetic acid at 0 - 20℃; for 3.5h;	100%
With sodium cyanoborohydride; acetic acid at 0 - 20℃; for 5h;	38%
With sodium cyanoborohydride; acetic acid at 0 - 20℃; for 3.5h; Inert atmosphere;	37.4%

2-(3-indole)-ethanol (526-55-6) + 3-dimethylaminomethyl-4-(3-fluorophenyl)-4-hydroxy-cyclohexanone (876932-36-4) → 1,1-(2-(dimethylaminomethyl)-3-hydroxy-3-(3-fluorophenyl)-pentamethylene)-1,3,4,9-tetrahydro-pyrano[3,4-b]indol

Conditions	Yield
Stage #1: 2-(3-indole)-ethanol; 3-dimethylaminomethyl-4-(3-fluorophenyl)-4-hydroxy-cyclohexanone With methanesulfonic acid In dichloromethane at 20℃; for 24h; Stage #2: With sodium hydroxide In water Stage #3: With sodium hydroxide In water	100%

2-(3-indole)-ethanol (526-55-6) → indole-3-acetaldehyde (2591-98-2)

Conditions	Yield
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In acetonitrile at 80℃; for 2h;	99%
With 2-iodoxybenzoic acid In acetonitrile at 80℃; for 3h;	91%
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide	87%

1H-imidazole (288-32-4) + 2-(3-indole)-ethanol (526-55-6) + tert-butyldimethylsilyl chloride (18162-48-6) → 1-O-tert-Butyldimethylsilyl-2-(3-indolyl)ethanol

Conditions	Yield
In N,N-dimethyl-formamide	99%
In N,N-dimethyl-formamide	99%

2-(3-indole)-ethanol (526-55-6) + 4-(Dimethylamino-phenyl-methyl)-cyclohexanone (943002-80-0) → 1,1-[3-(dimethylamino-(phenyl)-methyl)-pentamethylene]-1,3,4,9-tetrahydropyrano[3,4-b]indole (954420-64-5)

Conditions	Yield
Stage #1: 2-(3-indole)-ethanol; 4-(Dimethylamino-phenyl-methyl)-cyclohexanone With trifluorormethanesulfonic acid In dichloromethane at 20℃; for 6h; Stage #2: With sodium hydroxide; water In dichloromethane	99%

2-(3-indole)-ethanol (526-55-6) + 4-[(4-Chloro-phenyl)-dimethylamino-methyl]-cyclohexanone (943002-86-6) → 1,1-[3-(dimethylamino-(4-chlorophenyl)-methyl)-pentamethylene]-1,3,4,9-tetrahydro-pyrano[3,4-b]indole (954420-68-9)

Conditions	Yield
Stage #1: 2-(3-indole)-ethanol; 4-[(4-Chloro-phenyl)-dimethylamino-methyl]-cyclohexanone With trifluorormethanesulfonic acid In dichloromethane at 20℃; Stage #2: With sodium hydroxide; water In dichloromethane	99%

2-(3-indole)-ethanol (526-55-6) + methanesulfonic acid (75-75-2) + C17H24N2O → 4',9'-dihydro-4-(4-methylpiperazin-1-yl)-4-phenyl-3'H-spiro[cyclohexane-1,1'-pyrano[3,4-b]indole] methanesulfonate

Conditions	Yield
In dichloromethane at 20℃; for 4h;	99%

2-(3-indole)-ethanol (526-55-6) + tert-butyl (4,4-dimethoxycyclohexa-2,5-dien-1-ylidene)carbamate (106501-78-4) → di-tert-butyl (((3aS,8aS)-2,3-dihydro-8H-furo[2,3-b]indole-3a,8(8aH)-diyl)bis(4-methoxy-3,1-phenylene))dicarbamate

Conditions	Yield
With (R)-6,6'-bis(9-phenanthryl)-1,1'-spirobiindanyl-7,7'-diyl hydrogen phosphate In toluene at 30℃; for 12h; Molecular sieve; stereoselective reaction;	99%

2-(3-indole)-ethanol (526-55-6) + tert-butyl (4,4-diethoxycyclohexa-2,5-dien-1-ylidene)carbamate → di-tert-butyl (((3aR,8aR)-2,3-dihydro-8H-furo[2,3-b]indole-3a,8(8aH)-diyl)bis(4-ethoxy-3,1-phenylene))dicarbamate

Conditions	Yield
With (R)-6,6'-bis(9-phenanthryl)-1,1'-spirobiindanyl-7,7'-diyl hydrogen phosphate In toluene at 30℃; for 12h; Molecular sieve; stereoselective reaction;	99%

2-(3-indole)-ethanol (526-55-6) + (E)-(1-methyl-3-styryl-1H-indol-2-yl)diphenylmethanol → 2-(2-(4-methyl-2,3,3-triphenyl-1,2,3,4-tetrahydrocyclopenta[b]indol-1-yl)-1H-indol-3-yl)ethanol

Conditions	Yield
With toluene-4-sulfonic acid In chloroform at 40℃; for 8h; chemoselective reaction;	99%

2-(3-indole)-ethanol (526-55-6) + (E)-(5-methyl-3-styryl-1H-indol-2-yl)diphenylmethanol → 2-(1-(7-methyl-2,3,3-triphenyl-1,2,3,4-tetrahydrocyclopenta[b]-indol-1-yl)-1H-indol-3-yl)ethanol

Conditions	Yield
With toluene-4-sulfonic acid In chloroform at 30℃; for 3h; Molecular sieve; diastereoselective reaction;	99%

2-(3-indole)-ethanol (526-55-6) + (E)-(5-methyl-3-styryl-1H-indol-2-yl)diphenylmethanol → 2-(2-(7-methyl-2,3,3-triphenyl-1,2,3,4-tetrahydrocyclopenta[b]indol-1-yl)-1H-indol-3-yl)ethanol

Conditions	Yield
With toluene-4-sulfonic acid In chloroform at 40℃; for 8h; chemoselective reaction;	99%

2-(3-indole)-ethanol (526-55-6) + (E)-(3-(4-fluorostyryl)-1H-indol-2-yl)diphenylmethanol → 2-(2-(2-(4-fluorophenyl)-3,3-diphenyl-1,2,3,4-tetrahydrocyclopenta[b]indol-1-yl)-1H-indol-3-yl)ethanol

Conditions	Yield
With toluene-4-sulfonic acid In chloroform at 40℃; for 8h; chemoselective reaction;	99%

2-(3-indole)-ethanol (526-55-6) + (E)-(3-(3-chlorostyryl)-1H-indol-2-yl)diphenylmethanol → 2-(2-(2-(3-chlorophenyl)-3,3-diphenyl-1,2,3,4 -tetrahydrocyclopenta[b]indol-1-yl)-1H-indol-3-yl)ethanol

Conditions	Yield
With toluene-4-sulfonic acid In chloroform at 40℃; for 8h; chemoselective reaction;	99%

2-(3-indole)-ethanol (526-55-6) → C10H10N4O

Conditions	Yield
With 5,11,17,23,29,35-hexakis(tert-butyl)-37,38,39,40,41-hexakis(hydroxy)calix[6]arene; copper diacetate; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 1-butyl-2,3-methylimidazolium tetrafluoroborate In dimethyl sulfoxide at 45℃; for 1.5h; Solvent; Reagent/catalyst; Inert atmosphere;	98.5%

2-(3-indole)-ethanol (526-55-6) + 2,2-dimethoxy-propane (77-76-9) → 1,1-dimethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole (42821-17-0)

Conditions	Yield
With bismuth(lll) trifluoromethanesulfonate; water In toluene at 80℃; oxa Pictet-Spengler reaction;	98%
With iron(II) triflate In toluene at 70℃; for 24h; Pictet-Spengler Synthesis; Green chemistry;	98%

2-(3-indole)-ethanol (526-55-6) + buta-1,3-diene (106-99-0) → 3,3a,8,8a-tetrahydro-3a-(2,7-octadienyl)-2H-furo[2,3-b]indole

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; triethyl borane; palladium diacetate In tetrahydrofuran at 20℃; for 48h; Inert atmosphere; diastereoselective reaction;	98%

2-(3-indole)-ethanol (526-55-6) + methanesulfonic acid (75-75-2) + 4-morpholino-4-phenylcyclohexanone (1004548-07-5) → 4',9'-dihydro-4-morpholino-4-phenyl-3'H-spiro[cyclohexane-1,1'-pyrano[3,4-b]indole] methanesulfonate

Conditions	Yield
In dichloromethane at 20℃; for 16h;	98%

2-(3-indole)-ethanol (526-55-6) + 4-methylacetophenone dimethyl acetal (53578-01-1) → (R)-1-methyl-1-(p-tolyl)-1,3,4,9-tetrahydropyrano[3,4-b]indole

Conditions	Yield
With 2,3,4,5-tetrabromo-6-(((1R,2R)-2-(3-(4-nitro-3-(trifluoromethyl)phenyl)thioureido)-cyclohexyl)carbamoyl)benzoic acid In toluene at -30℃; for 18h; Pictet-Spengler Synthesis; Molecular sieve; Inert atmosphere; enantioselective reaction;	98%

2-(3-indole)-ethanol (526-55-6) + 3-Phenylpropenol (104-54-1) → C28H27NO

Conditions	Yield
With iron(II) triflate; (S)-(+)-N-(3,5-dioxa-4-phosphacyclohepta-[2,1-a;3,4-a′]dinaphthalen-4-yl)dibenz[b,f]azepine; bis(1,5-cyclooctadiene)diiridium(I) dichloride In diethyl ether at 20℃; for 8h; Reagent/catalyst; Time; Temperature; Solvent; enantioselective reaction;	97%

2-(3-indole)-ethanol (526-55-6) + (2-(3-bromophenyl)-3-oxocycloprop-1-enyl)methyl acetate → C20H16BrNO2

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In tetrahydrofuran at 25℃; for 5h; Molecular sieve; Inert atmosphere;	97%

2-(3-indole)-ethanol (526-55-6) + [bromo(difluoro)methyl](trimethyl)silane (115262-01-6) → 3-(2-(difluoromethoxy)ethyl)-1H-indole

Conditions	Yield
With potassium hydrogenfluoride In dichloromethane at 20℃; for 2h;	97%
With potassium hydrogen difluoride In dichloromethane; water at 20℃; for 10h; Reagent/catalyst;	93%

2-(3-indole)-ethanol (526-55-6) + (E)-diphenyl(3-styryl-1H-indol-2-yl)methanol → 2-(1-(2,3,3-triphenyl-1,2,3,4-tetrahydrocyclopenta[b]indol-1-yl)-1H-indol-3-yl)ethanol

Conditions	Yield
With toluene-4-sulfonic acid In chloroform at 30℃; for 3h; Catalytic behavior; Reagent/catalyst; Temperature; Solvent; Molecular sieve; diastereoselective reaction;	97%

Upstream product

• 87-51-4 indole-3-acetic acid 
• 1912-33-0 Indole-3-acetic acid methyl ester 
• 778-82-5 ethyl 3-indoleacetate 
• 2117-12-6 4-(trimethylsilyl)but-3-yn-1-ol 
• 615-43-0 2-iodophenylamine 
• 13436-46-9 2-ethoxytetrahydrofuran 
• 59-88-1 phenylhydrazine hydrochloride 
• 201230-82-2 carbon monoxide 
• 107-18-6 allyl alcohol 
• 100-63-0 phenylhydrazine 
• 18372-22-0 2-(3-indolyl)oxoacetic acid methyl ester 
• 1191-99-7 2,3-dihydro-2H-furan 
• 118313-87-4 2-Bromo-3-fluoroaniline hydrochloride 
• 62995-56-6 isobutyl 3-indolylglyoxylate 

Downstream Products

• 54518-02-4 3-Methyl-2,3,4',5'-tetrahydrofurano<2',3':2,3>indol 
• 3389-21-7 3-(2-bromoethyl)-1H-indole 
• 87-51-4 indole-3-acetic acid 
• 32933-86-1 3-(2-chloroethyl)indole 
• 41339-75-7 (1-butyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acid 
• 41339-73-5 (1-phenyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acid 
• 36505-82-5 1,3,4,9-tetrahydro-1-propyl-pyrano[3,4-b]indole-1-acetic acid 
• 41339-67-7 (1-ethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acid 
• 91360-99-5 <4-Dimethylaminophenyl>-bis-<3-(2-hydroxyethyl)-indol-2-yl>-methan 
• 129265-17-4 N,O-bis(phenylsulfonyl)tryptophol 
• 2591-98-2 indole-3-acetaldehyde 
• 284482-57-1 (3R,5R)-3-Benzoyloxymethyl-5-(1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-ylmethyl)-piperidine-1-carboxylic acid benzyl ester 
• 15741-82-9 (2-indol-3-yl-ethyl)-phenethyl-amine 
• 15741-79-4 N-benzyl tryptamine 

Relevant articles and documents

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SUBSTITUTED TETRAHYDROPYRANOINDOLES, DERIVATIVES THEREOF, AND THEIR METHODS OF SYNTHESIS AND USE

Disclosed herein are tetrahydropyranoindole compounds and derivatives thereof, as well as their methods of synthesis and use. The disclosed compounds may be synthesized by methods that utilize a cooperative hydrogen bond donor/Br?nsted acid system. The disclosed compounds may be useful for treating a disease, disorder, or a symptom thereof in a subject in need thereof, such as pain, swelling, and joint stiffness. The disclosed compounds also may be useful for treating cell proliferative diseases and disorders such as cancer.

AZEPINO-INDOLES AND OTHER HETEROCYCLES FOR TREATING BRAIN DISORDERS

The present invention provides azepino-indoles and other heterocycles and methods of using the compounds for treating brain disorders.

Synthesis of chiral [2,3]-fused indolines through enantioselective dearomatization inverse-electron-demand Diels-Alder reaction/oxidation of indoles with 2-(2-nitrovinyl)-1,4-benzoquinone

Enantioselective dearomatization inverse-electron-demand Diels-Alder reaction/oxidation of indoles with 2-(2-nitrovinyl)-1,4-benzoquinone was realised using a chiral bisoxazoline/zinc complex as a catalyst. This transformation allowed for the synthesis of enantioenriched six-membered [2,3]-fused indolines (up to 99% yield and 88% ee).