No renderable structure data available
BrC1C=CC2=C(C=1)C(C=O)=C(C(=O)OCC)N2[H]Chemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | ETHYL 5-BROMO-3-FORMYL-1H-INDOLE-2-CARBOXYLATE |
|---|---|
| IUPAC Name | — |
| CAS Number | 100123-25-9 |
| Database ID | 3275613 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
ETHYL 5-BROMO-3-FORMYL-1H-INDOLE-2-CARBOXYLATE (CAS 100123-25-9) 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 3275613
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
11 reactions · 11 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-993f91b7e4e348c39e7923c99ca86668Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The sub-title compound was prepared in accordance with step (c) Example 1 from 5-bromo-3-formylindole-2-carboxylic acid ethyl ester (4 g, 13.51 mmol; see step (a) above) and 4-isopropoxyphenylboronic acid (4.86 g, 27.02 mmol). Yield 4.1 g (710%).
Source ID: ord-64be0c8f489643f49869c1b0661d63fdConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Oxalyl chloride (3.43 mL, 39.9 mmol) was added with stirring to DMF (30 mL) and CH2Cl2 (80 mL) at 0° C. After 20 min at 0° C., 5-bromoindole-2-carboxylic acid ethyl ester (10 g, 37.3 mmol) in DMF (80 mL), was added. The mixture was stirred at rt for 24 h and poured into NaHCO3 (aq, sat) and extracted with CH2Cl2. The combined extracts were washed with H2O and brine, dried (Na2SO4) and concentrated. Crystallisation from EtOH gave the sub-title compound. Yield 8.9 g (81%). extracted with CH2Cl2 The combined extracts were washed with H2O and brine dried (Na2SO4) concentrated Crystallisation from EtOH
Source ID: ord-fc01060092af47e990830d0e312becc8Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The sub-title compound was prepared in accordance with step (c) Example 1 from 5-bromo-3-formylindole-2-carboxylic acid ethyl ester (4 g, 13.51 mmol; see step (a) above) and 4-isopropoxyphenylboronic acid (4.86 g, 27.02 mmol). Yield 4.1 g (710%).
Source ID: ord-64be0c8f489643f49869c1b0661d63fdConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Oxalyl chloride (3.43 mL, 39.9 mmol) was added with stirring to DMF (30 mL) and CH2Cl2 (80 mL) at 0° C. After 20 min at 0° C., 5-bromoindole-2-carboxylic acid ethyl ester (10 g, 37.3 mmol) in DMF (80 mL), was added. The mixture was stirred at rt for 24 h and poured into NaHCO3 (aq, sat) and extracted with CH2Cl2. The combined extracts were washed with H2O and brine, dried (Na2SO4) and concentrated. Crystallisation from EtOH gave the sub-title compound. Yield 8.9 g (81%). extracted with CH2Cl2 The combined extracts were washed with H2O and brine dried (Na2SO4) concentrated Crystallisation from EtOH
Source ID: ord-fc01060092af47e990830d0e312becc8Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-993f91b7e4e348c39e7923c99ca86668Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: In a 1 L round bottom flask 10.5 mL of phosphorus oxychloride was added to 15.5 g of N-methylformanilide at room temperature that resulted in a yellow solid after 15 min. At this time, 170 mL of 1,2-dichloroethane and 20.1 g of ethyl 5-bromoindole-2-carboxylate were added. The resulting suspension was heated under reflux for 4 hours and then concentrated to remove the organic solvent. 75 g of sodium acetate in 750 mL of water were added and the solid suspension was stirred for 30 min at room temperature, filtered and washed 3 times with water. The crude material was dried under vacuum for 1 hour and swished with 500 mL of EtOH to yield 21.2 g of the title compound as off-white solid. resulted in a yellow solid after 15 min The resulting suspension was heated under reflux for 4 hours concentrated to remove the organic solvent 75 g of sodium acetate in 750 mL of water were added filtered washed 3 times with water The crude material was dried under vacuum for 1 hour
Source ID: ord-93a02132d4ef49cf93f783faf08cdec1Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: In a 1 L round bottom flask 10.5 mL of phosphorus oxychloride was added to 15.5 g of N-methylformanilide at room temperature that resulted in a yellow solid after 15 min. At this time, 170 mL of 1,2-dichloroethane and 20.1 g of ethyl 5-bromoindole-2-carboxylate were added. The resulting suspension was heated under reflux for 4 hours and then concentrated to remove the organic solvent. 75 g of sodium acetate in 750 mL of water were added and the solid suspension was stirred for 30 min at room temperature, filtered and washed 3 times with water. The crude material was dried under vacuum for 1 hour and swished with 500 mL of EtOH to yield 21.2 g of the title compound as off-white solid. resulted in a yellow solid after 15 min The resulting suspension was heated under reflux for 4 hours concentrated to remove the organic solvent 75 g of sodium acetate in 750 mL of water were added filtered washed 3 times with water The crude material was dried under vacuum for 1 hour
Source ID: ord-93a02132d4ef49cf93f783faf08cdec1Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The sub-title compound was prepared in accordance with step (c) Example 1 from 5-bromo-3-formylindole-2-carboxylic acid ethyl ester (4 g, 13.51 mmol; see step (a) above) and 4-isopropoxyphenylboronic acid (4.86 g, 27.02 mmol). Yield 4.1 g (710%).
Source ID: ord-64be0c8f489643f49869c1b0661d63fdConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Oxalyl chloride (3.43 mL, 39.9 mmol) was added with stirring to DMF (30 mL) and CH2Cl2 (80 mL) at 0° C. After 20 min at 0° C., 5-bromoindole-2-carboxylic acid ethyl ester (10 g, 37.3 mmol) in DMF (80 mL), was added. The mixture was stirred at rt for 24 h and poured into NaHCO3 (aq, sat) and extracted with CH2Cl2. The combined extracts were washed with H2O and brine, dried (Na2SO4) and concentrated. Crystallisation from EtOH gave the sub-title compound. Yield 8.9 g (81%). extracted with CH2Cl2 The combined extracts were washed with H2O and brine dried (Na2SO4) concentrated Crystallisation from EtOH
Source ID: ord-fc01060092af47e990830d0e312becc8Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-993f91b7e4e348c39e7923c99ca86668PubChem References
These sources are listed in the compound's public database record.
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