86626-38-2 (4-溴二氢吲哚,4-bromo-2,3-dihydro-1H-indole)

反应条件：

1.1 Reagents: Potassium carbonate Solvents: Butyronitrile ; 1 h, 200 °C

参考文献：

Regioselective Formation of Substituted Indoles: Formal Synthesis of Lysergic Acid

Points, Gary L. III ; et al, Chemistry - A European Journal, 2020, 26(70), 16655-16658

合成路线：1 步

52488-36-5

_86%

反应条件：

1.1 Reagents: Potassium tert-butoxide , Hydrogen Catalysts: (OC-6-42)-Bromodicarbonyl[2-(diphenylphosphino-κP)-N-[2-(diphenylphosphino-κP)et… Solvents: Toluene ; 36 h, 50 bar, rt → 100 °C

参考文献：

Hydrogenation or Dehydrogenation of N-Containing Heterocycles Catalyzed by a Single Manganese Complex

Zubar, Viktoriia; et al, Organic Letters, 2020, 22(10), 3974-3978

合成路线：2 步

2566738-36-9

2566738-30-3

反应条件：

1.1 Reagents: 2,6-Di-tert-butylpyridine Solvents: Dichloromethane ; 18 h, 40 °C
2.1 Reagents: Potassium carbonate Solvents: Butyronitrile ; 1 h, 200 °C

参考文献：

Regioselective Formation of Substituted Indoles: Formal Synthesis of Lysergic Acid

Points, Gary L. III ; et al, Chemistry - A European Journal, 2020, 26(70), 16655-16658

合成路线：3 步

2566738-28-9

反应条件：

1.1 Reagents: p-Toluenesulfonic acid Solvents: Water ; 0 °C; 0 °C → rt; 4 h, rt
2.1 Reagents: 2,6-Di-tert-butylpyridine Solvents: Dichloromethane ; 18 h, 40 °C
3.1 Reagents: Potassium carbonate Solvents: Butyronitrile ; 1 h, 200 °C

参考文献：

Regioselective Formation of Substituted Indoles: Formal Synthesis of Lysergic Acid

Points, Gary L. III ; et al, Chemistry - A European Journal, 2020, 26(70), 16655-16658

合成路线：3 步

4544-38-1

358-23-6

反应条件：

1.1 Reagents: 2,4,6-Trimethylpyridine Solvents: Dichloromethane ; 0 °C; 10 min, 0 °C
2.1 Reagents: 2,6-Di-tert-butylpyridine Solvents: Dichloromethane ; 18 h, 40 °C
3.1 Reagents: Potassium carbonate Solvents: Butyronitrile ; 1 h, 200 °C

参考文献：

Regioselective Formation of Substituted Indoles: Formal Synthesis of Lysergic Acid

Points, Gary L. III ; et al, Chemistry - A European Journal, 2020, 26(70), 16655-16658

合成路线：4 步

1256469-25-6

4248-19-5

反应条件：

1.1 Reagents: Cesium carbonate Catalysts: Tris(dibenzylideneacetone)dipalladium , 2-(Di-tert-butylphosphino)biphenyl Solvents: Benzene ; rt → 70 °C
1.2 Solvents: Water ; 1.5 h, 70 °C
2.1 Reagents: p-Toluenesulfonic acid Solvents: Water ; 0 °C; 0 °C → rt; 4 h, rt
3.1 Reagents: 2,6-Di-tert-butylpyridine Solvents: Dichloromethane ; 18 h, 40 °C
4.1 Reagents: Potassium carbonate Solvents: Butyronitrile ; 1 h, 200 °C

参考文献：

Regioselective Formation of Substituted Indoles: Formal Synthesis of Lysergic Acid

Points, Gary L. III ; et al, Chemistry - A European Journal, 2020, 26(70), 16655-16658

合成路线：4 步

927-74-2

反应条件：

1.1 Reagents: N-Bromosuccinimide Catalysts: Silver nitrate Solvents: Acetone ; 6 h, rt
2.1 Reagents: 2,4,6-Trimethylpyridine Solvents: Dichloromethane ; 0 °C; 10 min, 0 °C
3.1 Reagents: 2,6-Di-tert-butylpyridine Solvents: Dichloromethane ; 18 h, 40 °C
4.1 Reagents: Potassium carbonate Solvents: Butyronitrile ; 1 h, 200 °C

参考文献：

Regioselective Formation of Substituted Indoles: Formal Synthesis of Lysergic Acid

Points, Gary L. III ; et al, Chemistry - A European Journal, 2020, 26(70), 16655-16658

合成路线：5 步

496-64-0

358-23-6

反应条件：

1.1 Reagents: 2,4,6-Trimethylpyridine Solvents: Dichloromethane ; 15 min, -78 °C
1.2 Reagents: Hydrochloric acid Solvents: Water
2.1 Reagents: Cesium carbonate Catalysts: Tris(dibenzylideneacetone)dipalladium , 2-(Di-tert-butylphosphino)biphenyl Solvents: Benzene ; rt → 70 °C
2.2 Solvents: Water ; 1.5 h, 70 °C
3.1 Reagents: p-Toluenesulfonic acid Solvents: Water ; 0 °C; 0 °C → rt; 4 h, rt
4.1 Reagents: 2,6-Di-tert-butylpyridine Solvents: Dichloromethane ; 18 h, 40 °C
5.1 Reagents: Potassium carbonate Solvents: Butyronitrile ; 1 h, 200 °C

参考文献：

Regioselective Formation of Substituted Indoles: Formal Synthesis of Lysergic Acid

Points, Gary L. III ; et al, Chemistry - A European Journal, 2020, 26(70), 16655-16658

合成路线：6 步

526-99-8

反应条件：

1.1 Reagents: Phosphorus pentoxide , Tripotassium phosphate Solvents: 1,2-Dichlorobenzene ; 20 h, 160 °C
2.1 Reagents: 2,4,6-Trimethylpyridine Solvents: Dichloromethane ; 15 min, -78 °C
2.2 Reagents: Hydrochloric acid Solvents: Water
3.1 Reagents: Cesium carbonate Catalysts: Tris(dibenzylideneacetone)dipalladium , 2-(Di-tert-butylphosphino)biphenyl Solvents: Benzene ; rt → 70 °C
3.2 Solvents: Water ; 1.5 h, 70 °C
4.1 Reagents: p-Toluenesulfonic acid Solvents: Water ; 0 °C; 0 °C → rt; 4 h, rt
5.1 Reagents: 2,6-Di-tert-butylpyridine Solvents: Dichloromethane ; 18 h, 40 °C
6.1 Reagents: Potassium carbonate Solvents: Butyronitrile ; 1 h, 200 °C

参考文献：

Regioselective Formation of Substituted Indoles: Formal Synthesis of Lysergic Acid

Points, Gary L. III ; et al, Chemistry - A European Journal, 2020, 26(70), 16655-16658

合成路线：1 步

496-15-1

_62%

反应条件：

1.1 Reagents: Hydrochloric acid Catalysts: Aluminum chloride Solvents: Dichloromethane
1.2 Reagents: Bromine Catalysts: Aluminum chloride

参考文献：

Hydroxylation and bromination of indolines and tetrahydroquinoline in superacids

Berrier, C.; et al, New Journal of Chemistry, 1987, 11(8-9), 605-9

合成路线：1 步

496-15-1

反应条件：

1.1 Reagents: Sulfuric acid , Silver sulfate ; 30 min, rt
1.2 Reagents: Bromine ; 30 min, rt
1.3 Reagents: Sodium hydroxide Solvents: Water ; basified, cooled

参考文献：

Concerning the preparation of 6-bromotryptamine

Scott Wiens, P.; et al, Tetrahedron, 2021, 85,

合成路线：1 步

反应条件：

1.1 Reagents: Hydrofluoric acid , Antimony pentafluoride

参考文献：

Hydroxylation and bromination of indolines and tetrahydroquinoline in superacids

Berrier, C.; et al, New Journal of Chemistry, 1987, 11(8-9), 605-9

合成路线：1 步

反应条件：

1.1 Reagents: Hydrofluoric acid , Antimony pentafluoride

参考文献：

Hydroxylation and bromination of indolines and tetrahydroquinoline in superacids

Berrier, C.; et al, New Journal of Chemistry, 1987, 11(8-9), 605-9

合成路线：2 步

120-72-9

反应条件：

1.1 Reagents: Sodium cyanoborohydride Solvents: Acetic acid ; 2 h, 15 °C
1.2 Reagents: Sodium hydroxide Solvents: Water ; basified, cooled
2.1 Reagents: Sulfuric acid , Silver sulfate ; 30 min, rt
2.2 Reagents: Bromine ; 30 min, rt
2.3 Reagents: Sodium hydroxide Solvents: Water ; basified, cooled

参考文献：

Concerning the preparation of 6-bromotryptamine

Scott Wiens, P.; et al, Tetrahedron, 2021, 85,

合成路线：2 步

反应条件：

1.1 Reagents: Hydrofluoric acid , Antimony pentafluoride
2.1 Reagents: Hydrofluoric acid , Antimony pentafluoride

参考文献：

Hydroxylation and bromination of indolines and tetrahydroquinoline in superacids

Berrier, C.; et al, New Journal of Chemistry, 1987, 11(8-9), 605-9

合成路线：2 步

496-15-1

反应条件：

1.1 Reagents: Hydrochloric acid Catalysts: Aluminum chloride Solvents: Dichloromethane
1.2 Reagents: Bromine Catalysts: Aluminum chloride
2.1 Reagents: Hydrofluoric acid , Antimony pentafluoride

参考文献：

Hydroxylation and bromination of indolines and tetrahydroquinoline in superacids

Berrier, C.; et al, New Journal of Chemistry, 1987, 11(8-9), 605-9

合成路线：2 步

反应条件：

1.1 Reagents: Hydrofluoric acid , Antimony pentafluoride
2.1 Reagents: Hydrofluoric acid , Antimony pentafluoride

参考文献：

Hydroxylation and bromination of indolines and tetrahydroquinoline in superacids

Berrier, C.; et al, New Journal of Chemistry, 1987, 11(8-9), 605-9

合成路线：2 步