No renderable structure data available
C1=CC=C2C(=C1)C(=O)N(C2=O)CCC3=CNC4=CC=CC=C43Chemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 2-[2-(1H-indol-3-yl)ethyl]isoindole-1,3-dione |
|---|---|
| IUPAC Name | — |
| CAS Number | 15741-71-6 |
| Database ID | 288577 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
2-[2-(1H-indol-3-yl)ethyl]isoindole-1,3-dione (CAS 15741-71-6) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 288577
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-b1d8773a48654795bdd24f3db2ca5034Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-8d6fa4562bb545f2b23414e32ce641f6Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of tryptamine (3.04 g, 19.0 mmol) and phthalic anhydride (3.0 g, 20.0 mmol) in toluene (300 ml) was boiled under reflux for 12 h using a water separator. The solvent was removed i. vac. and the residue was recrystallized from methylene chloride/cyclohexane. Yield: 4.46 g (81%) under reflux for 12 h The solvent was removed i and the residue was recrystallized from methylene chloride/cyclohexane
Source ID: ord-10e4f6e9b27f4f91a28a43a56083ab90Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Tryptamine (3.04 g, 19.0 mmol) and phthalic anhydride (3.00 g, 20.0 mmol) were boiled for 12 h in a water separator. The solvent was distilled off i. vac. and the residue was dissolved in methylene chloride. Product was precipitated out by addition of cyclohexane and the precipitate was filtered off with suction and dried. Yield: 4.46 g (Ind-1; 87%) The solvent was distilled off i and the residue was dissolved in methylene chloride Product was precipitated out by addition of cyclohexane the precipitate was filtered off with suction dried
Source ID: ord-0a5628519f784d81817ffed9b15b6109Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2-[2-(1H-indol-3-yl)-ethyl]-1H-isoindole-1,3(2H)dione (3.77 g, 13.0 mmol) in dry THF (0.13 L) under argon was added NEt3 (1.84 mL, 13.0 mmol). This mixture was cooled to −78° C., and neat t-BuOCl (1.54 mL, 13.0 mmol) was added. The reaction mixture was stirred for 30 min at −78° C. A solution of 9-(3-methyl-2-butenyl)9-bora-bicyclo[3.3.1]nonane (40 mmol) in hexanes was added. The reaction mixture was stirred for 6 h at −78° C. It was quenched with 1 M aq HCl, and permitted to warm to rt overnight. The reaction mixture was extracted with CH2Cl2. The CH2Cl2 extracts were dried, filtered, and concentrated to give an oil. The oil was purified by silica chromatography to give the title compound: TLC Rf=0.36 (CH2Cl2); MS (ESI+) m/z 381.2, 359.2; 1H NMR (300 MHz, CDCl3) δ 7.91 (1H), 7.88-7.69 (5H), 7.29 (1H), 7.10 (2H), 6.18 (1H), 5.25 (2H), 3.95 (2H), 3.16 (2H), 1.61 (6H). The reaction mixture was stirred for 6 h at −78° C It was quenched with 1 M aq HCl to warm to rt overnight The reaction mixture was extracted with CH2Cl2 The CH2Cl2 extracts were dried filtered concentrated to give an oil The oil was purified by silica chromatography
Source ID: ord-2588537b4fc741dabd62aaa99a37a4fdConditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2-[2-(1H-indol-3-yl)-ethyl]-1H-isoindole-1,3(2H)dione (3.77 g, 13.0 mmol) in dry THF (0.13 L) under argon was added NEt3 (1.84 mL, 13.0 mmol). This mixture was cooled to −78° C., and neat t-BuOCl (1.54 mL, 13.0 mmol) was added. The reaction mixture was stirred for 30 min at −78° C. A solution of 9-(3-methyl-2-butenyl)9-bora-bicyclo[3.3.1]nonane (40 mmol) in hexanes was added. The reaction mixture was stirred for 6 h at −78° C. It was quenched with 1 M aq HCl, and permitted to warm to rt overnight. The reaction mixture was extracted with CH2Cl2. The CH2Cl2 extracts were dried, filtered, and concentrated to give an oil. The oil was purified by silica chromatography to give the title compound: TLC Rf=0.36 (CH2Cl2); MS (ESI+) m/z 381.2, 359.2; 1H NMR (300 MHz, CDCl3) δ 7.91 (1H), 7.88-7.69 (5H), 7.29 (1H), 7.10 (2H), 6.18 (1H), 5.25 (2H), 3.95 (2H), 3.16 (2H), 1.61 (6H). The reaction mixture was stirred for 6 h at −78° C It was quenched with 1 M aq HCl to warm to rt overnight The reaction mixture was extracted with CH2Cl2 The CH2Cl2 extracts were dried filtered concentrated to give an oil The oil was purified by silica chromatography
Source ID: ord-2588537b4fc741dabd62aaa99a37a4fdConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-b1d8773a48654795bdd24f3db2ca5034Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-8d6fa4562bb545f2b23414e32ce641f6Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2-[2-(1H-indol-3-yl)ethyl]-1H-isoindole-1,3(2H)-dione (3.77 g, 13.0 mmol) in dry THF (0.13 L) under argon was added NEt3 (1.84 mL, 13.0 mmol). This mixture was cooled to -78° C., and neat t-BuOCl (1.54 mL, 13.0 mmol) was added. The reaction mixture was stirred for 30 min at −78° C. A solution of 9-(3-methyl-2-butenyl)-9-bora-bicyclo[3.3.1]nonane (40 mmol) in hexanes was added. The reaction mixture was stirred for 6 h at −78° C. It was quenched with 1 M aq HCl, and permitted to warm to rt overnight. The reaction mixture was extracted with CH2Cl2. The CH2Cl2 extracts were dried, filtered, and concentrated to give an oil. The oil was purified by silica chromatography to give the title compound: TLC Rf=0.36 (CH2Cl2); MS (ESI+) m/z 381.2, 359.2; 1H NMR (300 MHz, CDCl3) δ 7.91 (1H), 7.88-7.69 (5H), 7.29 (1H), 7.10 (2H), 6.18 (1H), 5.25 (2H), 3.95 (2H), 3.16 (2H), 1.61 (6H). The reaction mixture was stirred for 6 h at −78° C It was quenched with 1 M aq HCl to warm to rt overnight The reaction mixture was extracted with CH2Cl2 The CH2Cl2 extracts were dried filtered concentrated to give an oil The oil was purified by silica chromatography
Source ID: ord-69afa475b03e48118c28a91252df78a4Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: This compound was prepared by the reaction of tryptamine and N-carboethoxyphthalimide: TLC Rf=0.36 (CH2Cl2); MS (ESI+) m/z 291.0.
Source ID: ord-85cb0eaa65574e36b0f4ba9a12a78602Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2-[2-(1H-indol-3-yl)ethyl]-1H-isoindole-1,3(2H)-dione (3.77 g, 13.0 mmol) in dry THF (0.13 L) under argon was added NEt3 (1.84 mL, 13.0 mmol). This mixture was cooled to -78° C., and neat t-BuOCl (1.54 mL, 13.0 mmol) was added. The reaction mixture was stirred for 30 min at −78° C. A solution of 9-(3-methyl-2-butenyl)-9-bora-bicyclo[3.3.1]nonane (40 mmol) in hexanes was added. The reaction mixture was stirred for 6 h at −78° C. It was quenched with 1 M aq HCl, and permitted to warm to rt overnight. The reaction mixture was extracted with CH2Cl2. The CH2Cl2 extracts were dried, filtered, and concentrated to give an oil. The oil was purified by silica chromatography to give the title compound: TLC Rf=0.36 (CH2Cl2); MS (ESI+) m/z 381.2, 359.2; 1H NMR (300 MHz, CDCl3) δ 7.91 (1H), 7.88-7.69 (5H), 7.29 (1H), 7.10 (2H), 6.18 (1H), 5.25 (2H), 3.95 (2H), 3.16 (2H), 1.61 (6H). The reaction mixture was stirred for 6 h at −78° C It was quenched with 1 M aq HCl to warm to rt overnight The reaction mixture was extracted with CH2Cl2 The CH2Cl2 extracts were dried filtered concentrated to give an oil The oil was purified by silica chromatography
Source ID: ord-69afa475b03e48118c28a91252df78a4Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: This compound was prepared by the reaction of tryptamine and N-carboethoxyphthalimide: TLC Rf=0.36 (CH2Cl2); MS (ESI+) m/z 291.0.
Source ID: ord-85cb0eaa65574e36b0f4ba9a12a78602PubChem References
These sources are listed in the compound's public database record.
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