875-79-6 (1,2-二甲基吲哚,1,2-dimethyl-1H-indole)

反应条件：

1.1 Catalysts: Tris(pentafluorophenyl)borane Solvents: Methyl-d3benzene ; rt → 120 °C; 0.75 h, 120 °C

参考文献：

Frustrated Lewis Pair Catalyzed Dehydrogenative Oxidation of Indolines and Other Heterocycles

Maier, Alexander F. G.; et al, Angewandte Chemie, 2016, 55(40), 12219-12223

合成路线：1 步

26216-93-3

_98%

反应条件：

1.1 Catalysts: Di-μ-chlorobis[(1,2,5,6-η)-1,5-cyclooctadiene]diiridium , 1,2-Bis(diphenylphosphino)benzene (crosslinked, polystyrene-bound) Solvents: p-Xylene ; 5 min, rt
1.2 20 h, 130 °C

参考文献：

Ir-Catalyzed Reversible Acceptorless Dehydrogenation/Hydrogenation of N-Substituted and Unsubstituted Heterocycles Enabled by a Polymer-Cross-Linking Bisphosphine

Zhang, Deliang; et al, Organic Letters, 2020, 22(13), 5240-5245

合成路线：1 步

_99%

反应条件：

1.1 Reagents: Sodium hydride Solvents: Dimethylformamide ; 0 °C → rt; 30 min, rt; rt → 0 °C
1.2 0 °C; 0 °C → rt
1.3 Reagents: Water ; rt

参考文献：

Cu-Catalyzed Oxidation of C2 and C3 Alkyl-Substituted Indole via Acyl Nitroso Reagents

Zhang, Jun ; et al, Organic Letters, 2019, 21(1), 14-17

合成路线：1 步

_99%

反应条件：

1.1 Catalysts: Sodium hydride Solvents: Tetrahydrofuran ; 30 min, 0 °C
1.2 Solvents: Tetrahydrofuran ; 0 °C; 12 h, rt

参考文献：

Design, synthesis and biological evaluation of novel 2-sulfonylindoles as potential anti-inflammatory therapeutic agents for treatment of acute lung injury

Xia, Qinqin ; et al, European Journal of Medicinal Chemistry, 2018, 160, 120-132

合成路线：1 步

_97%

反应条件：

1.1 Reagents: Sodium hydride Solvents: Dimethylformamide ; 30 min, rt
1.2 16 h, rt

参考文献：

Indole Naphthyridinones as Inhibitors of Bacterial Enoyl-ACP Reductases FabI and FabK

Seefeld, Mark A.; et al, Journal of Medicinal Chemistry, 2003, 46(9), 1627-1635

合成路线：1 步

158585-43-4

_94%

反应条件：

1.1 Reagents: 2-Mercaptobenzoic acid Catalysts: Trifluoroacetic acid Solvents: Trifluoroacetic acid

参考文献：

Nonreductive Desulfenylation of 3-Indolyl Sulfides. Improved Syntheses of 2-Substituted Indoles and 2-Indolyl Sulfides

Hamel, Pierre; et al, Journal of Organic Chemistry, 1994, 59(21), 6372-7

合成路线：1 步

57056-93-6

591-87-7

_88%

反应条件：

1.1 Reagents: Potassium carbonate , Tetrabutylammonium chloride , Oxygen Catalysts: Palladium chloride Solvents: Dimethylacetamide ; 12 h, 100 °C

参考文献：

Palladium-Catalyzed Selective Heck-Type Diarylation of Allylic Esters with Aryl Halides Involving a β-OAc Elimination Process

Liu, Yan; et al, Organic Letters, 2011, 13(5), 1126-1129

合成路线：1 步

74-83-9

_81%

反应条件：

1.1 Reagents: Potassium hydroxide Solvents: Dimethylformamide ; 30 min, rt
1.2 cooled; 96 h, rt

参考文献：

Exploration and Development of a C-H-Activated Route to Access the [1,2]Dithiolo[4,3-b]indole-3(4H)-thione Core and Related Derivatives

Asquith, Christopher R. M. ; et al, Synlett, 2019, 30(2), 156-160

合成路线：1 步

74-83-9

反应条件：

1.1 Reagents: Sodium hydride Solvents: Dimethylformamide ; 0 °C; 30 min, 0 °C
1.2 overnight, 0 °C

参考文献：

Tryptamine Synthesis by Iron Porphyrin Catalyzed C-H Functionalization of Indoles with Diazoacetonitrile

Hock, Katharina J. ; et al, Angewandte Chemie, 2019, 58(11), 3630-3634

合成路线：1 步

74-83-9

反应条件：

1.1 Reagents: Sodium hydride Solvents: Dimethylformamide ; 0 °C; 30 min, 0 °C
1.2 overnight, 0 °C

参考文献：

Iron-catalyzed C-H insertions: organometallic and enzymatic carbene transfer reactions

Hock, Katharina J.; et al, ChemRxiv, 2018, 1, 1-17

合成路线：1 步

29456-04-0

6832-87-7

_79%

参考文献：

Indole synthesis via SRN1 reactions

Bard, Raymond R.; et al, Journal of Organic Chemistry, 1980, 45(8), 1546-7

合成路线：1 步

1997317-94-8

1184-58-3

_68%

反应条件：

1.1 Reagents: Lithium chloride Catalysts: Bis(acetylacetonato)nickel , 1,3-Bis(diphenylphosphino)propane Solvents: Hexane , 1,4-Dioxane ; 16 h, 170 °C; 170 °C → rt

参考文献：

Decarbonylative Methylation of Aromatic Esters by a Nickel Catalyst

Okita, Toshimasa; et al, Organic Letters, 2018, 20(10), 3132-3135

合成路线：1 步

611-21-2

_65%

反应条件：

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran
1.2 Reagents: Carbon dioxide
1.3 Reagents: Butyllithium
1.4 Reagents: Hydrochloric acid Solvents: Water

参考文献：

Carbon dioxide: a reagent for the simultaneous protection of nucleophilic centers and the activation of alternative locations to electrophilic attack. 16. A novel synthetic method for the side-chain functionalization of N-methyl-o-toluidine and for the preparation of 2-substituted N-methylindoles

Katritzky, Alan R.; et al, Heterocycles, 1990, 30(1), 407-14

合成路线：1 步

_65%

反应条件：

1.1 Reagents: Sodium hydride Solvents: Dimethylformamide ; 0 °C; 1 h, 0 °C; overnight, 0 °C
1.2 Reagents: Ammonium chloride Solvents: Water

参考文献：

A domino reaction for generating β-aryl aldehydes from alkynes by substrate recognition catalysis

Fang, Weiwei ; et al, Nature Communications, 2019, 10(1),

合成路线：1 步

65962-98-3

19164-60-4

_64%

反应条件：

1.1 Solvents: 1,1,1,3,3,3-Hexafluoro-2-propanol ; 0 °C → 25 °C; 3 h, 25 °C

参考文献：

From Cycloalkanols to Heterocycles via Nitrogen Insertion

Sandvoss, Alexander; et al, Organic Letters, 2023, 25(31), 5795-5799

合成路线：1 步

16136-58-6

_61%

反应条件：

1.1 Reagents: Trimethylboroxin , Pivalic anhydride Catalysts: Palladium diacetate , 1,1′-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis[1,1-diphenylphosphine] Solvents: Tetrahydrofuran , 1,4-Dioxane ; 24 h, 160 °C

参考文献：

Palladium-catalyzed decarbonylative methylation of aryl carboxylic acids

Feng, Boya; et al, Organic Chemistry Frontiers, 2022, 9(4), 1085-1089

合成路线：1 步

2417963-00-7

_61%

反应条件：

1.1 Reagents: 1-Octanethiol Catalysts: Trifluoromethanesulfonic acid Solvents: Dichloromethane ; 12 h, 23 °C
1.2 Reagents: Sodium bicarbonate Solvents: Water ; 10 min, 23 °C

参考文献：

Facile C-S Bond Cleavage of Aryl Sulfoxides Promoted by Bronsted Acid

Brutiu, Bogdan R.; et al, Synlett, 2021, 32(5), 488-490

合成路线：1 步

603-76-9

_58%

反应条件：

1.1 Reagents: Sodium hydride Solvents: Dimethylformamide ; rt; 30 min, rt
1.2 30 min, 0 °C; 0 °C → rt; overnight, rt
1.3 Solvents: Water

参考文献：

Friedel-Crafts Acylation of Pyrroles and Indoles using 1,5-Diazabicyclo[4.3.0]non-5-ene (DBN) as a Nucleophilic Catalyst

Taylor, James E.; et al, Organic Letters, 2010, 12(24), 5740-5743

合成路线：1 步

917-54-4

42108-38-3

_53%

反应条件：

1.1 Reagents: Titanocene dichloride Solvents: Diethyl ether , Toluene ; -5 °C; 1 h, -5 °C; 1 h, rt; rt → 0 °C
1.2 Reagents: Ammonium chloride Solvents: Water ; cooled
1.3 Solvents: Toluene ; 72 h, reflux

参考文献：

Synthesis of indoles via alkylidenation of acyl hydrazides

Hisler, Kevin; et al, Tetrahedron Letters, 2009, 50(26), 3290-3293

合成路线：1 步

173436-68-5

865-33-8

_51%

反应条件：

1.1 Solvents: Acetonitrile ; rt
1.2 Reagents: Water ; rt

参考文献：

Detosylative (Deutero)alkylation of Indoles and Phenols with (Deutero)alkoxides

Zhu, Ming-Hui; et al, Organic Letters, 2019, 21(17), 7073-7077

合成路线：1 步

37493-34-8

1184-58-3

_48%

反应条件：

1.1 Catalysts: Benzenesulfonic acid, 4-methyl-, nickel(2+) salt (2:1) , 1,1′-(3,4-Thiophenediyl)bis[1,1-dicyclohexylphosphine] Solvents: Hexane , 1,4-Dioxane ; 16 h, 170 °C; 170 °C → rt

参考文献：

Decarbonylative Methylation of Aromatic Esters by a Nickel Catalyst

Okita, Toshimasa; et al, Organic Letters, 2018, 20(10), 3132-3135

合成路线：1 步

603-76-9

80-48-8

_45%

反应条件：

1.1 Reagents: Butyllithium Solvents: Diethyl ether

参考文献：

Heteroatom-facilitated lithiations

Gschwend, Heinz W.; et al, Organic Reactions (Hoboken, 1979, 26,

合成路线：1 步

37493-34-8

_41%

反应条件：

1.1 Reagents: Potassium tert-butoxide , 1,1,3,3-Tetramethyldisiloxane Catalysts: Bis(1,5-cyclooctadiene)nickel , 1H-Imidazolium, 1,3-dicyclohexyl-, tetrafluoroborate(1-) (1:1) Solvents: Toluene ; 10 h, 110 °C; 110 °C → rt
1.2 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ; rt; rt → 65 °C; 2 h, 65 °C

参考文献：

Exhaustive Reduction of Esters Enabled by Nickel Catalysis

Cook, Adam; et al, Journal of the American Chemical Society, 2020, 142(18), 8109-8115

合成路线：1 步

77129-87-4

_30%

参考文献：

Photochemical investigations of 4-(N-methylanilino)-pent-3-en-2-one

Watson, Darrell; et al, Texas Journal of Science, 1980, 32(4), 357-61

合成路线：2 步

77129-87-4