3558-24-5

Basic information

• Product Name: 1-Methyl-2-phenylindole
• Synonyms: 1-methyl-2-phenyl-1h-indol;1-METHYL-2-PHENYLINDOLE;1-METHYL-2-PHENYL-1H-INDOLE;N-METHYL-2-PHENYLINDOLE;1-Methyl-2-Phenylindol;1-METHYL-2-PHENYLINDOLE 99+%;1H-Indole, 1-methyl-2-phenyl-;2-Phenyl-N-methylindole
• CAS NO: 3558-24-5
• Molecular Formula: C15H13N
• Molecular Weight: 207.27
• EINECS: 222-618-1
• Product Categories: Intermediates of Dyes and Pigments;Indole;Indoles;Simple Indoles;Building Blocks;Heterocyclic Building Blocks;Heterocycle-Indole series;intermediates
• Mol File: 3558-24-5.mol
• Article Data: 155

Chemical Properties

• Melting Point: 98-100 °C(lit.)
• Boiling Point: 336.3°C (rough estimate)
• Flash Point: 184.1 °C
• Appearance: white to light green-tan crystals or crystal powder
• Density: 1.0880 (rough estimate)
• Vapor Pressure: 1.17E-05mmHg at 25°C
• Refractive Index: 1.5720 (estimate)
• Storage Temp.: 2-8°C
• BRN: 148770
• CAS DataBase Reference: 1-Methyl-2-phenylindole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Methyl-2-phenylindole(3558-24-5)
• EPA Substance Registry System: 1-Methyl-2-phenylindole(3558-24-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-26
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 3558-24-5(Hazardous Substances Data)

Usage

Chemical Properties

WHITE TO LIGHT GREEN-TAN CRYSTALS OR CRYST. POWDER

Uses

Reactant for preparation of: Cyano indolesDifluorohydroxy indolesReactant for:Carboxylation of indolesAllylation of indolesFormylation of indolesNitrosylation of indoles

Synthesis Reference(s)

Tetrahedron Letters, 34, p. 2059, 1993 DOI: 10.1016/S0040-4039(00)60345-3

General Description

Reaction of 1-methyl-2-phenylindole with nitrogen dioxide or with nitrous acid (NaNO2-CH3COOH) in benzene has been studied. 1-Methyl-2-phenylindole is reported to react with malondialdehyde (MDA) and 4-hydroxyalkenals to afford a stable chromophore with intense maximal absorbance at 586nm.

InChI:InChI=1/C15H13N/c1-16-14-10-6-5-9-13(14)11-15(16)12-7-3-2-4-8-12/h2-11H,1H3

Synthetic route

N-methyl-2-(2-phenylethynyl)aniline (170956-92-0) → 1-methyl-2-phenyl-1H-indole (3558-24-5)

Conditions	Yield
With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); silver trifluoromethanesulfonate In 1,2-dichloro-ethane at 20℃; for 0.0166667h; Catalytic behavior; Sealed tube;	100%
With silver nitrate In acetonitrile at 80℃; for 8h; Reagent/catalyst; Temperature; Solvent; Time;	99%
With [(THD-Dipp)AuCl]; silver trifluoromethanesulfonate In ethanol at 20℃; for 0.5h; Reagent/catalyst; Inert atmosphere; Schlenk technique;	97%

1-methyl-2-phenylindoline (20878-31-3, 65053-50-1, 65053-51-2) → 1-methyl-2-phenyl-1H-indole (3558-24-5)

Conditions	Yield
With ferrocene; tris(pentafluorophenyl)borate In toluene at 120℃; under 75.0075 Torr; for 16.5h; Inert atmosphere; Schlenk technique; Glovebox;	99%
With N-hydroxyphthalimide In acetonitrile at 80℃; for 6h; Sealed tube;	74%
With N-hydroxyphthalimide In acetonitrile at 80℃; for 6h;	74%

2-phenyl-indole (948-65-2) + carbonic acid dimethyl ester (616-38-6) → 1-methyl-2-phenyl-1H-indole (3558-24-5)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 90℃; for 28h; Product distribution; Further Variations:; Temperatures; Solvents; Pressures; Reagents; reaction times; microwave irradiation;	98%
With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide at 94 - 95℃; for 24h;	97%

1-methylindole (603-76-9) + diphenyliodonium tetrafluoroborate → 1-methyl-2-phenyl-1H-indole (3558-24-5)

Conditions	Yield
With Pd2[(C6H4)PPh2]2[CF3C(O)CHC(O)CF3]2 In acetic acid at 24.84℃; for 30h; Reagent/catalyst; Time; Solvent; Inert atmosphere; Schlenk technique;	98%
With palladium containing [Zr6O4(OH)4(terephthalate)4.75(1,2,4,5-benzenetetracarboxylate)1.25] at 80℃; for 5h; Reagent/catalyst; Concentration;	94%
With (1,3-di(2,4,6-(CH3)3-C6H2)-imidazol-2-ylidene)Pd(OAc)2; acetic acid at 25℃; for 18h;	86%
With palladium diacetate In ethanol at 50℃; for 24h; Kinetics; Reagent/catalyst;	51%

1-methylindole (603-76-9) + diphenyliodonium hexafluorophosphate (58109-40-3) → 1-methyl-2-phenyl-1H-indole (3558-24-5)

Conditions	Yield
With Pd2[(C6H4)PPh2]2[CF3C(O)CHC(O)CF3]2 In acetic acid at 24.84℃; for 30h; Catalytic behavior; Reagent/catalyst; Time; Solvent; Inert atmosphere; Schlenk technique;	98%
Stage #1: 1-methylindole With Pd2[(C6H4)PPh2]2[O2CC6H5]2; acetic acid at 24.84℃; for 0.0833333h; Inert atmosphere; Schlenk technique; Stage #2: diphenyliodonium hexafluorophosphate at 24.84℃; for 10h; Reagent/catalyst; Inert atmosphere; Schlenk technique;	97%

2-phenyl-indole (948-65-2) + tetramethylammonium fluoride (373-68-2) → 1-methyl-2-phenyl-1H-indole (3558-24-5)

Conditions	Yield
In toluene at 100℃; for 6h;	98%

2,3-dibromo-1-methyl-1H-indole (128746-62-3) + phenylboronic acid (98-80-6) → 1-methyl-2-phenyl-1H-indole (3558-24-5)

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 90℃; for 6h; Suzuki-Miyaura Coupling;	97%

1-methylindole (603-76-9) + iodobenzene (591-50-4) → 1-methyl-2-phenyl-1H-indole (3558-24-5)

Conditions	Yield
With potassium phosphate; palladium bis(2,2,6,6-tetramethyl-3,5-heptanedionate) In 1-methyl-pyrrolidin-2-one at 125℃; for 36h;	96%
With water; palladium diacetate; silver cyclohexanecarboxylate at 30℃; for 16h; Time; Reagent/catalyst;	93%
With ortho-nitrobenzoic acid; silver(l) oxide; palladium diacetate In N,N-dimethyl-formamide at 25℃; for 7h; Product distribution; Further Variations:; Reagents;	92%

2-phenylethynylaniline (13141-38-3) + methyl iodide (74-88-4) → 1-methyl-2-phenyl-1H-indole (3558-24-5)

Conditions	Yield
Stage #1: 2-phenylethynylaniline With potassium hydride In 1-methyl-pyrrolidin-2-one at 20℃; for 2h; Stage #2: methyl iodide In 1-methyl-pyrrolidin-2-one for 0.5h;	96%

1-bromo-2-(phenylethenyl)benzene (21375-88-2) + methylamine (74-89-5) → 1-methyl-2-phenyl-1H-indole (3558-24-5)

Conditions	Yield
With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; OTips-DalPhos; potassium tert-butylate In toluene at 90℃; for 12h; Reagent/catalyst; Buchwald-Hartwig Coupling; Inert atmosphere; Sealed tube;	95%
With (R)-1-[(SP)-2-(dicyclohexylphosphino)ferrocenyl]ethyldi-tert-butylphosphine; bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; potassium tert-butylate In tetrahydrofuran; toluene at 90℃; Inert atmosphere;	88%
With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; OTips-DalPhos; potassium tert-butylate In tetrahydrofuran; toluene at 90℃; for 12h; Sealed vial;	83%

N,N-dimethyl-2-(2-phenylethynyl)aniline (54655-08-2) → 1-methyl-2-phenyl-1H-indole (3558-24-5)

Conditions	Yield
With toluene-4-sulfonic acid; silver(l) oxide at 40℃; for 3h;	95%
With ethanol at 120℃; for 10h; Microwave irradiation; Inert atmosphere; Green chemistry;	93%
With toluene-4-sulfonic acid; silver(l) oxide In N,N-dimethyl-formamide at 60℃; for 12h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Schlenk technique;	88%
Multi-step reaction with 2 steps 1.1: iron(III) chloride / dichloromethane / 0.33 h / 25 °C 1.2: air / 24 h / 25 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 0 °C / Inert atmosphere 2.2: 0 - 25 °C / Inert atmosphere View Scheme

2-phenyl-indole (948-65-2) + methyl iodide (74-88-4) → 1-methyl-2-phenyl-1H-indole (3558-24-5)

Conditions	Yield
Stage #1: 2-phenyl-indole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1h; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃;	94%
Stage #1: 2-phenyl-indole With potassium hydroxide In N,N-dimethyl-formamide at 0℃; for 0.25h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 0 - 20℃; for 6h;	93%
Stage #1: 2-phenyl-indole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 24h;	90%

2-(tributylstannyl)furan (118486-94-5) + N-methyl-2-(2-phenylethynyl)aniline (170956-92-0) → 1-methyl-2-phenyl-1H-indole (3558-24-5)

Conditions	Yield
With silver hexafluoroantimonate In 1,2-dichloro-ethane at 80℃; Inert atmosphere; Glovebox; Schlenk technique;	91%

1-methylindole (603-76-9) + 3,3-diethyl-1-phenyltriazene (13056-98-9) → 1-methyl-2-phenyl-1H-indole (3558-24-5)

Conditions	Yield
With C9H18N2O3S*H2O4S; palladium diacetate In water; N,N-dimethyl-formamide at 20℃; for 5h; Reagent/catalyst; regioselective reaction;	91%

2-phenyl-indole (948-65-2) + dimethyl sulfate (77-78-1) → 1-methyl-2-phenyl-1H-indole (3558-24-5)

Conditions	Yield
With sodium hydroxide 60 degC 30 min then 80-90 degC 1 h;	90%

1-methylindole (603-76-9) + chlorobenzene (108-90-7) → 1-methyl-2-phenyl-1H-indole (3558-24-5)

Conditions	Yield
Stage #1: 1-methylindole With 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran; hexane; pentane at 20℃; for 0.5h; Inert atmosphere; Stage #2: chlorobenzene In tetrahydrofuran; hexane; pentane at 20℃; for 1.5h; Inert atmosphere;	90%
With cesium acetate In N,N-dimethyl-formamide at 150℃; for 48h; under air;	21%

1-methylindole (603-76-9) + benzenediazonium tetrafluoroborate (369-57-3) → 1-methyl-2-phenyl-1H-indole (3558-24-5)

Conditions	Yield
Stage #1: 1-methylindole With palladium diacetate In 2-methyltetrahydrofuran; ethyl acetate for 2h; Stage #2: benzenediazonium tetrafluoroborate In 2-methyltetrahydrofuran; ethyl acetate at 20℃; for 0.5h; Catalytic behavior; Solvent; Reagent/catalyst;	90%

styrene oxide (96-09-3) + N-methylaniline (100-61-8) → 1-methyl-2-phenyl-1H-indole (3558-24-5)

Conditions	Yield
Stage #1: styrene oxide; N-methylaniline With zinc trifluoromethanesulfonate at 20℃; for 1h; Inert atmosphere; Stage #2: With 1,1'-bis-(diphenylphosphino)ferrocene; dodecacarbonyl-triangulo-triruthenium; toluene-4-sulfonic acid In 1,4-dioxane at 150℃; for 22h; Inert atmosphere; regioselective reaction;	89%

1-methylindole (603-76-9) + iodobenzene (591-50-4) → N-methyl-3-phenylindole (30020-98-5) + 1-methyl-2-phenyl-1H-indole (3558-24-5)

Conditions	Yield
With palladium dichloride In dimethyl sulfoxide; acetonitrile at 100℃; for 8h; Catalytic behavior; Time; Reagent/catalyst; Temperature; Solvent; regioselective reaction;	A n/a B 88%
With 2,6-bis[(N-phenyl)imino]phenylpalladium bromide; potassium acetate at 80℃; for 24h; Reagent/catalyst; Solvent; Time; Overall yield = 98 %Chromat.; regioselective reaction;	A n/a B 85%
With PdBr2(bipy)*DMSO; silver carbonate In 1,4-dioxane at 150℃; for 13h; Inert atmosphere;	A n/a B 60%
With potassium acetate In water at 100℃; for 24h; Overall yield = 73.4 %;
With sodium acetate; palladium dichloride In water; N,N-dimethyl-formamide at 140℃; Reagent/catalyst; regioselective reaction;

1-methylindole (603-76-9) + benzenesufonyl hydrazide (80-17-1) → 1-methyl-2-phenyl-1H-indole (3558-24-5)

Conditions	Yield
With trifluorormethanesulfonic acid; oxygen; C39H47N3O4Pd In dimethyl sulfoxide at 60℃; under 760.051 Torr; for 24h; Reagent/catalyst; Sealed tube;	88%
With trifluorormethanesulfonic acid; oxygen; palladium diacetate In dimethyl sulfoxide at 70℃; under 760.051 Torr; for 20h;	84%

1-methylindole (603-76-9) + phenylboronic acid (98-80-6) → 1-methyl-2-phenyl-1H-indole (3558-24-5)

Conditions	Yield
With palladium 10% on activated carbon; silver trifluoroacetate In methanol at 50℃; for 7h; Reagent/catalyst; Solvent; regioselective reaction;	86%
With [bis(acetoxy)iodo]benzene; palladium diacetate In acetic acid at 20℃; for 16h;	84%
With oxygen; palladium diacetate; acetic acid at 20℃; Schlenk technique;	80%

methyl-phenyl-thioether (100-68-5) + C9H8ClNZn*LiCl → 1-methyl-2-phenyl-1H-indole (3558-24-5)

Conditions	Yield
Stage #1: C9H8ClNZn*LiCl With trans-[1,3-bis(2,6-diisopropylphenyl)imidazolin-2-ylidene]PdCl2(NC5H5) In tetrahydrofuran at 20℃; for 0.05h; Inert atmosphere; Stage #2: methyl-phenyl-thioether In tetrahydrofuran; acetonitrile at 20℃; for 3h; Inert atmosphere;	86%

1-methylindole (603-76-9) + 3,3-dimethyl-1-phenyltriazene (7227-91-0) → 1-methyl-2-phenyl-1H-indole (3558-24-5)

Conditions	Yield
With C9H18N2O3S*H2O4S; palladium diacetate In water; N,N-dimethyl-formamide at 20℃; for 5h; Reagent/catalyst; regioselective reaction;	86%

1-methylindole (603-76-9) + tetraphenyltin(IV) (595-90-4) → 1-methyl-2-phenyl-1H-indole (3558-24-5)

Conditions	Yield
With [Pd(OTs)2(MeCN)2]; oxygen; acetic acid at 25℃; for 12h; Reagent/catalyst; Temperature; Schlenk technique;	86%

1-methylindole (603-76-9) + 3,3-diethyl-1-phenyltriaz-1-ene (13056-98-9) → 1-methyl-2-phenyl-1H-indole (3558-24-5)

Conditions	Yield
With boron trifluoride diethyl etherate; palladium diacetate In N,N-dimethyl acetamide at 80℃; for 12h; Sealed tube;	85%

C23H26BN → 1-methyl-2-phenyl-1H-indole (3558-24-5)

Conditions	Yield
With water In benzene-d6 for 0.0833333h; Inert atmosphere;	85%

3-(tert-butylthio)-1-methyl-2-phenylindole → 1-methyl-2-phenyl-1H-indole (3558-24-5)

Conditions	Yield
With thiosalicilyc acid; trifluoroacetic acid at 72℃; for 1.5h;	84%
With thiosalicilyc acid In trifluoroacetic acid at 72℃; for 1.5h;	84%
With thiosalicilyc acid; trifluoroacetic acid at 72℃; for 1.5h; Mechanism; further 3-indolyl sulfides;	84%

2C6H16N2(2+)Na(1-)*C36H32N4Mg(2-) + iodobenzene (591-50-4) → 1-methyl-2-phenyl-1H-indole (3558-24-5)

Conditions	Yield
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride	84%

1-methylindole (603-76-9) + (E)-1-phenyl-2-(pyrrolidin-1-yl)diazene (36719-71-8) → 1-methyl-2-phenyl-1H-indole (3558-24-5)

Conditions	Yield
With hexafluorophosphoric acid; palladium diacetate In water; N,N-dimethyl-formamide at 0 - 20℃; for 4h; Catalytic behavior; Concentration; Reagent/catalyst; Solvent; Temperature; regioselective reaction;	84%

1-methyl-2-phenyl-1H-indole (3558-24-5) + diphenyl diselenide (1666-13-3) → 1-Methyl-2-phenyl-3-(phenylselenyl)-1H-indole (1094425-08-7)

Conditions	Yield
With potassium iodate; glycerol In neat (no solvent) at 100℃; for 6h; Inert atmosphere; Schlenk technique;	100%
With Rose Bengal lactone In acetonitrile at 20℃; for 6h; Schlenk technique; Irradiation;	99%
With iodine; dimethyl sulfoxide In neat (no solvent) at 80℃; for 0.0833333h; Microwave irradiation; Sealed tube; Green chemistry;	95%

1-methyl-2-phenyl-1H-indole (3558-24-5) + diphenyldisulfane (882-33-7) → 1-methyl-2-phenyl-3-(phenylsulfenyl)indole (82946-84-7)

Conditions	Yield
With potassium iodate; glycerol In neat (no solvent) at 100℃; for 6h; Inert atmosphere; Schlenk technique;	100%
With sodium tetrafluoroborate; potassium iodide In acetonitrile at 60℃; for 12h; Electrolysis;	89%
With sodium tetrafluoroborate; potassium iodide In acetonitrile at 60℃; for 12h; Electrochemical reaction;	89%
With ammonium iodide; water; acetic acid; dimethyl sulfoxide at 110℃; for 6h; Green chemistry; regioselective reaction;	77%
With sodium iodide In acetonitrile at 20℃; for 18h; Irradiation;	52%

1-methyl-2-phenyl-1H-indole (3558-24-5) → 3-bromo-1-methyl-2-phenyl-1H-indole

Conditions	Yield
With hydrogen bromide; dimethyl sulfoxide In water; ethyl acetate at 60℃; for 0.166667h;	99%
With N-Bromosuccinimide In chloroform at 20℃; for 0.5h;	97%
With tetrabutylammomium bromide; sodium hydrogencarbonate; Selectfluor In toluene at 20℃; for 2h; Reagent/catalyst; Solvent; Schlenk technique; regioselective reaction;	96%

1-methyl-2-phenyl-1H-indole (3558-24-5) + di(isopropyl) 2-(3-phenylprop-2-enyl)-2-(prop-2-ynyl)malonate → (R)-diisopropyl 3-((R)-(1-methyl-2-phenyl-1H-indol-3-yl)(phenyl)methyl)-4-methylenecyclopentane-1,1-dicarboxylate (1135130-14-1)

Conditions	Yield
With (R)-4-MeO-3,5-(t-Bu)2MeOBIPHEP(AuCl)2; silver trifluoromethanesulfonate In diethyl ether at 20℃; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	99%

1-methyl-2-phenyl-1H-indole (3558-24-5) + di(isopropyl) 2-(3-phenylprop-2-enyl)-2-(prop-2-ynyl)malonate → C36H39NO4

Conditions	Yield
With (R)-4-MeO-3,5-(t-Bu)2-MeOBIPHEP(AuCl)2; silver trifluoromethanesulfonate In diethyl ether at 20℃; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	99%

1-methyl-2-phenyl-1H-indole (3558-24-5) → 3-iodo-1-methyl-2-phenyl 1H-indole (452962-71-9)

Conditions	Yield
With 1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione; 4,4'-dimethoxyphenyl disulfide In acetonitrile at 20℃; for 0.75h;	99%
With 1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione; diphenyldisulfane In acetonitrile at 20℃; for 1.5h;	99%
With sodium hydrogencarbonate; Selectfluor; potassium iodide In toluene at 20℃; for 2h; Reagent/catalyst; Schlenk technique; regioselective reaction;	96%
With ammonium iodide; sulfuric acid; dimethyl sulfoxide In ethyl acetate at 60℃; for 5h;	94%
With [bis(acetoxy)iodo]benzene; sodium iodide In water; acetonitrile at 20℃; regioselective reaction;	94%

1-methyl-2-phenyl-1H-indole (3558-24-5) + 6,6-Diphenylfulvene (2175-90-8) → 3-(4-(diphenylmethylene)cyclopent-2-enyl)-1-methyl-2-phenyl-1H-indole

Conditions	Yield
With copper(II) bis(trifluoromethanesulfonate) In acetonitrile at 25℃; for 2h; regioselective reaction;	99%

1-methyl-2-phenyl-1H-indole (3558-24-5) + ammonium thiocyanate (1147550-11-5) → 1-methyl-2-phenyl-3-thiocyanato-1H-indole

Conditions	Yield
In acetonitrile at 20℃; for 3h; Electrochemical reaction; Inert atmosphere;	99%
With oxygen In tetrahydrofuran at 25℃; under 750.075 Torr; for 10h; Irradiation;	95%
With Oxone In methanol at 20℃; for 0.5h;	87%
With TiO2/MoS2 In acetonitrile at 20℃; for 16h; Irradiation;	84%

1-methyl-2-phenyl-1H-indole (3558-24-5) + 2,2-dihydroxy-1-phenyl-ethanone (1075-06-5) + dimedone (126-81-8) → C31H27NO3

Conditions	Yield
With 7.78 wtpercent Cu supported on porous hypercrosslinked polymer (from N,N'-dibenzylbenzimidazolium chloride and benzene) In ethanol at 80℃; for 3h;	99%

1-methyl-2-phenyl-1H-indole (3558-24-5) + p-Chlorothiophenol (106-54-7) → 3-((4-chlorophenyl)thio)-1-methyl-2-phenyl-1H-indole (1346164-88-2)

Conditions	Yield
With lithium perchlorate In acetonitrile at 20℃; for 3h; Inert atmosphere; Electrochemical reaction;	99%

1-methyl-2-phenyl-1H-indole (3558-24-5) + 3,3-diethyl-1-phenyltriazene (13056-98-9) → (E)-1-methyl-2-phenyl-3-(phenyldiazenyl)-1H-indole

Conditions	Yield
With C8H16N2*BrH*FeCl3 In 2,2,2-trifluoroethanol at 0 - 20℃; for 2h; Reagent/catalyst; regioselective reaction;	99%

1-methyl-2-phenyl-1H-indole (3558-24-5) + 2-((trifluoromethyl)sulfonyl)benzo[d]thiazole → 1-methyl-2-phenyl-3-((trifluoromethyl)sulfinyl)-1H-indole

Conditions	Yield
With Diphenylphosphinic chloride In acetonitrile at 60℃; for 1h; Schlenk technique; Inert atmosphere;	99%

1-methyl-2-phenyl-1H-indole (3558-24-5) + carbon dioxide (124-38-9) → 2-phenyl-1-methylindole-3-carboxylic acid (59050-41-8)

Conditions	Yield
With dimethylaluminum chloride In hexane; toluene at 80℃; under 22502.3 Torr; for 3h; Autoclave;	98%
With dimethylaluminum chloride In hexane; toluene at 20℃; under 22502.3 Torr; for 3h; Friedel-Crafts reaction; regioselective reaction;	61%
With N,N-dimethyl-aniline In acetonitrile Irradiation;	2.5%

4-hydroxy[1]benzopyran-2-one (1076-38-6) + 1-methyl-2-phenyl-1H-indole (3558-24-5) + 2-chloro-benzaldehyde (89-98-5) → 3-[(2-chlorophenyl)(1-methyl-2-phenyl-1H-indol-3-yl)-methyl]-4-hydroxy-2H-chromen-2-one (1609076-44-9)

Conditions	Yield
With L-proline In ethanol at 80℃; for 4h;	98%

1-methyl-2-phenyl-1H-indole (3558-24-5) + 2-((difluoromethyl)thio)isoindoline-1,3-dione → 3-((difluoromethyl)thio)-1-methyl-2-phenyl-1H-indole

Conditions	Yield
With chloro-trimethyl-silane In 1,2-dichloro-ethane at 80 - 120℃; for 16h; Schlenk technique;	98%
With chloro-trimethyl-silane at 80 - 120℃; Inert atmosphere; Sealed tube;	98%

1-methyl-2-phenyl-1H-indole (3558-24-5) + C17H19NO2 → 1,3-dimethyl-2-phenyl-1H-indole (3558-28-9)

Conditions	Yield
With tris(pentafluorophenyl)borate In 1,2-dichloro-ethane at 95℃; for 16h;	98%

1-methyl-2-phenyl-1H-indole (3558-24-5) + N-benzyl-N-(p-toluenesulfonyl)-2-phenylethynylamine (609769-63-3) → (Z)-N-benzyl-4-methyl-N-(1-(1-methyl-2-phenyl-1H-indol-3-yl)-2-phenylvinyl)benzenesulfonamide

Conditions	Yield
With erbium(III) triflate In 1,2-dichloro-ethane at 70℃; for 2h; regioselective reaction;	98%
With erbium(III) triflate In 1,2-dichloro-ethane at 70℃; for 2h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature;	98%

1-methyl-2-phenyl-1H-indole (3558-24-5) + cyanoacetic acid (372-09-8) → 3-(1-methyl-2-phenyl-1H-indol-3-yl)-3-oxopropanenitrile

Conditions	Yield
With acetic anhydride at 90℃; for 1h;	97%
With propionic acid anhydride at 65 - 75℃; for 0.116667h;	93%

(E)‐1‐(1‐methyl‐1H‐imidazole‐2‐yl)‐but‐2‐en‐1‐one (860772-38-9) + 1-methyl-2-phenyl-1H-indole (3558-24-5) → (S)-1-(1-methyl-1H-imidazole-2-yl)-3-(1-methyl-2-phenyl-1H-indol-3-yl)butan-1-one

Conditions	Yield
With C38H38IrN4O2(1+)*F6P(1-) In tetrahydrofuran at 20℃; for 40h; Friedel-Crafts Alkylation; Inert atmosphere; enantioselective reaction;	97%

(1H-indol-3-yl)(phenyl)methanol (51626-58-5) + 1-methyl-2-phenyl-1H-indole (3558-24-5) → 3-((1H-indol-3-yl)(phenyl)methyl)-1-methyl-2-phenyl-1H-indole (78602-03-6)

Conditions	Yield
With silica gel In toluene at 20℃; for 2h; Friedel-Crafts Alkylation;	97%
With 2,2,2-trifluoroethanol at 20℃; Sealed tube; Green chemistry;	72%

1-methyl-2-phenyl-1H-indole (3558-24-5) + 1,1,3,3,3-pentafluoro-2-trimethylsiloxypropene (53841-59-1) → 1,1,1,3,3-pentafluoro-2-(1-methyl-2-phenyl-1H-indol-3-yl)propan-2-ol

Conditions	Yield
With copper(l) chloride In 1,2-dichloro-ethane at 80℃; for 16h; Inert atmosphere;	97%
With copper(l) chloride In 1,2-dichloro-ethane at 80℃; for 24h; Inert atmosphere;	97%

Upstream product

• 79461-73-7 methylammonium sulfite 
• 71858-76-9 1-methyl-2-(2-benzoylethyl)pyridinium iodide 
• 496043-95-9 methyl-[2-(2-oxo-2-phenyl-ethyl)-phenyl]-carbamic acid tert-butyl ester 
• 396094-74-9 2-[2'-(N-Boc-N-methylamino)phenyl]-1,3-dithiane 
• 591-50-4 iodobenzene 
• 56741-25-4 1-phenyl-3-(pyridin-2-yl)propan-1-one 
• 1170697-26-3 benzoic acid N,N'-dimethyl-N'-phenylhydrazide 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 618-40-6 1-Methyl-1-phenylhydrazine 
• 98-86-2 acetophenone 
• 603-76-9 1-methylindole 
• 58109-40-3 diphenyliodonium hexafluorophosphate 
• 618-41-7 Benzenesulfinic acid 
• 873-55-2 sodium benzenesulfonate 

Downstream Products

• 67335-29-9 bis(1-methyl-2-phenyl-1H-indol-3-yl)methane 
• 102174-06-1 (1-methyl-2-phenyl-indol-3-yl)-glyoxylic acid dimethylamide 
• 102313-73-5 1-[(1-methyl-2-phenyl-indol-3-yl)-oxoacetyl]-piperidine 
• 856812-88-9 2,2-bis-(1-methyl-2-phenyl-indol-3-yl)-propionitrile 
• 1757-72-8 1-methyl-2-phenyl-1H-indole-3-carbaldehyde 
• 53603-63-7 1-methyl-2-phenyl-3-nitroso-1H-indole 
• 69742-18-3 6-methoxy-3-methyl-2-(1-methyl-2-phenyl-indol-3-ylazo)-benzothiazolium; methyl sulfate 
• 88848-27-5 1-Methyl-3-[(Z)-2-methyl-3-(1-methyl-2-phenyl-1H-indol-3-yl)-prop-2-en-(E)-ylidene]-2-phenyl-3H-indolium; chloride 
• 50670-26-3 1-Methyl-3-[(E)-3-(1-methyl-2-phenyl-1H-indol-3-yl)-prop-2-en-(E)-ylidene]-2-phenyl-3H-indolium; chloride 
• 82946-84-7 1-methyl-2-phenyl-3-(phenylthio)-1H-indole 
• 79573-76-5 3-[(Z)-2-Chloro-3-(1-methyl-2-phenyl-1H-indol-3-yl)-prop-2-en-(E)-ylidene]-1-methyl-2-phenyl-3H-indolium; chloride 
• 79573-77-6 3-[(Z)-2-Bromo-3-(1-methyl-2-phenyl-1H-indol-3-yl)-prop-2-en-(E)-ylidene]-1-methyl-2-phenyl-3H-indolium; chloride 
• 114155-19-0 (+/-)-3,3,3-trifluoro-2-hydroxy-2-(1-methyl-2-phenylindol-3-yl)propionic acid methyl ester 
• 122631-44-1 (E)-1-methyl-3-(2-nitrovinyl)-2-phenyl-1H-indole 

Relevant articles and documents

Trans-Aminoboration across Internal Alkynes Catalyzed by B(C6F5)3 for the Synthesis of Borylated Indoles

We report here a facile B(C6F5)3 catalyzed trans-aminoboration of internal alkynes, furnishing 3-position borylated indoles at ambient temperature. This reaction proceeds with the breaking of a B-N bond and the formation of N-C and B-C bonds to produce indole and derivatives in one step. It works well for various boron reagents and alkynyl-anilines. The borylated indoles can be further derivatized to give column stable organoboron compounds that can be used for future functionalization.

Structurally-defined direct C-magnesiation and C-zincation of N-heterocyclic aromatic compounds using alkali-metal-mediated metallation

Demonstrating direct synergic "low polarity metallation", 1-methylindole is C-magnesiated by (TMEDA)2·Na 2MgBu4 and C-zincated by (TMEDA)·Na( tBu)(TMP)Zn(tBu), and 1-methylpyrrole is C-zincated by the same reagent, with all three metal products successfully crystallographically characterised. The Royal Society of Chemistry.

PALLADIUM-PHOSPHINE COMPLEX CATALYZED CROSS-COUPLING REACTION OF 1-METHYL-2-PYRROLYL-MAGNESIUM BROMIDE AND -ZINC CHLORIDE WITH ORGANIC HALIDES

1-Methyl-2-pyrrolyl-magnesium bromide and -zinc chloride, which were prepared from 1-methyl-2-pyrrolyllithium with MgBr2 and ZnCl2 respectively, reacted with aryl- and heteroaromatic halides to give the corresponding 2-substituted pyrroles in good to excellent yields in the presence of palladium-phosphine complexes as catalysts.

B(C6F5)3-Catalyzed Electron Donor-Acceptor Complex-Mediated Aerobic Sulfenylation of Indoles under Visible-Light Conditions

An efficient B(C6F5)3-catalyzed aerobic oxidative C-S cross-coupling reaction of thiophenol with indoles was developed, affording a wide range of diaryl sulfides in good yields. An electron donor-acceptor complex between B(C6F5)3 and indoles was formed, facilitating the photoinduced single-electron transfer (SET) from indole substrates to the B(C6F5)3 catalyst. This protocol demonstrates a new reaction model using B(C6F5)3 as a single-electron oxidant.

Tris-NHC-propagated self-supported polymer-based Pd catalysts for heterogeneous C-H functionalization

Three-dimensionally propagated imidazolium-containing mesoporous coordination polymer and organic polymer-based platforms were successfully exploited to develop single-site heterogenized Pd-NHC catalysts for oxidative arene/heteroarene C-H functionalization reactions. The catalysts were efficient in directed arene halogenation, and nondirected arene and heteroarene arylation reactions. High catalytic activity, excellent heterogeneity and recyclability were offered by these systems making them promising candidates in the area of heterogeneous C-H functionalization, where efficient catalysts are still scarce.