Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | ||||||
{[ item.p_purity ]} | {[ item.pr_size ]} | Inquiry |
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price) ]} |
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price) ]} | {[ item.pr_usastock ]} | in stock Inquiry - | {[ item.pr_chinastock ]} | {[ item.pr_remark ]} in stock Inquiry - | Login | Inquiry |
Please Login or Create an Account to: See VIP prices and availability
CAS No. : | 93247-78-0 | MDL No. : | MFCD00211064 |
Formula : | C10H9NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FTLOEULOTNVCGF-UHFFFAOYSA-N |
M.W : | 175.18 | Pubchem ID : | 676694 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | Example 1 Preparation of P001 Indole-7 carboxyldehyde (I-1). Ethyl Indole-7 m carboxylate was prepared according to literature procedure {Batcho B. and Leimgruber, K., Org. Syn. Vol IIV, page 34-40). To a solution of methyl 7-indolecarboxylate (13 g, 74.2 mmol) in 250 ml of anhydrous THF was added LiAlH4 (10.9 g, 0.288 mol) in portions, and reaction mixture was heated to reflux for 2 h. After cooling to room temperature, the excess hydride was quenched by addition of water (12 mL), 15percent NaOH (12 mL) and water (26 mL). The solids were removed by filtration through a pad of Celite and filtrate was evaporated in vacuo to yield (1H-indol-7-yl)-methanol (10.7 g, 98percent). 1H-NMR (CDCl3). | |
98% | Example 17; Preparation of Al3; Indole-7 carboxyldehyde (K-44); Methyl 7-indolecarboxylate was prepared according to literature procedure {Batcho B. and Leimgruber, K., Org. Syn. VoI HV, page 34-40). To a solution of methyl 7-indolecarboxylate (13 g, 74.2 mmol) in anhydrous THF (250 niL) was added LiAlH4 (10.9 g, 0.288 mol) in portions, and reaction mixture was heated to reflux for 2h. After cooling to room temperature, the excess hydride was quenched by addition of water (12mL), 15percent NaOH (12mL) and water (26mL). The solids were removed by filtration through a pad of Celite and filtrate was evaporated in vacuo to yield (lH-indol-7-yl)- methanol (10.7 g, 98percent). 1HNMR (CDCl3). To a solution of the alcohol, (IH- indol-7-yl)-methanol (8.0 g, 54.3 mmol) in 400 mL of methylene chloride was added activated manganese (IV) oxide (85percent, 41.0 g, 0.40 mol), and stirred at ambient temperature for 72h. After additional of 200 mL of methylene chloride and 400 mL of methanol to the reaction mixture, the whole mixture was filtered through a pad of silica gel to remove solid materials. The filtrate was concentrated to afford a crude product, which was purified by a column chromatography on silica gel to yield lH-indole-7-carbaldehyde, K-44 (6.55 g, 83percent). | |
With acetic acid; In tetrahydrofuran; ethyl acetate n-hexane; | iii) 7-Indole methanol Solid lithium aluminum hydride (1.0 g) was added in portions over 1 hour to a stirred solution of methyl 7-indolecarboxylate (6.7 g) in tetrahydrofuran (100 ml). The mixture was stirred for a further 2 hours then excess lithium aluminium hydride was destroyed by addition of acetic acid, the mixture was diluted with aqueous sodium hydroxide and extracted with ethyl acetate. The extract was dried and evaporated and the residue was chromatographed on silica in ethyl acetate-hexane (1:9 to 1:2) to give the product. |
With acetic acid; In tetrahydrofuran; ethyl acetate n-hexane; | Part C Preparation of 7-Indole Methanol Solid lithium aluminum hydride (1.0 g) is added in portions over 1 hour to a stirred solution of methyl 7-indolecarboxylate (6.7 g) in tetrahydrofuran (100 ml). The mixture was stirred for a further 2 hours then excess lithium aluminum hydride was destroyed by addition of acetic acid, the mixture is diluted with aqueous sodium hydroxide and extracted with ethyl acetate. The extract is dried and evaporated and the residue is chromatographed on silica in ethyl acetate-hexane (1:9 to 1:2) to give the product. | |
With acetic acid; In tetrahydrofuran; ethyl acetate n-hexane; | iii) 7-Indole methanol Solid lithium aluminium hydride (10 g) was added in portions over 1 hour to a stirred solution of methyl 7-indole-carboxylate (6.7 g) in tetrahydrofuran (100 ml). The mixture was stirred for a further 2 hours then excess lithium aluminium hydride was destroyed by addition of acetic acid, the mixture was diluted with aqueous sodium hydroxide and extracted with ethyl acetate. The extract was dried and evaporated and the residue was chromatographed on silica in ethyl acetate-hexane (1:9 to 1:2) to give the product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
palladium on charcoal; In toluene; | ii) Methyl 7-indolecarboxylate A solution of methyl 3-[2-(E)-(dimethylamino)ethenyl]-2-nitrobenzoate (12.0 g, 48 mmol) in toluene (200 ml) was hydrogenated at 60 psi over 10percent palladium on charcoal (1.5 g) until hydrogen uptake ceased. The catalyst was filtered off, the filtrate was evaporated and the residue was chromatographed on silica to give the product. | |
palladium on charcoal; In toluene; | Part B Preparation of Methyl 7-indolecarboxylate A solution of methyl 3-[2-(E)-(dimethylamino)ethenyl]-2-nitrobenzoate (12.0 g, 48 mmol) in toluene (200 ml) is hydrogenated at 60 psi (4.22 Kg/cm2) over 10percent palladium on charcoal (1.5 g) until hydrogen uptake ceased. The catalyst is filtered off, the filtrate is evaporated and the residue is chromatographed on silica to give the product. | |
palladium on charcoal; In toluene; | ii) Methyl 7-indolecarboxylate A solution of methyl 3-[2-(E)-(dimethylamino)ethenyl]- 2-nitrobenzoate (12.0 g, 48 mmol) in toluene (200 ml) was hydrogenated at 60 psi over 10percent palladium on charcoal (1.5 g) until hydrogen uptake ceased. The catalyst was filtered off, the filtrate was evaporated and the residue was chromatographed on silica to give the product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(Intermediate Example 33) 1-Methyl-1H-indole-7-carboxylic acid Methyl 1H-indole-7-carboxylate (546 mg) was dissolved in N,N-dimethylformamide (8 ml) and cooler to 0C. Sodium hydride (370 mg) was added thereto and stirred as such for 30 minutes. Methyl iodide (0.38 ml) was added slowly dropwise thereto, and the mixture was warmed to room temperature and stirred for 2 hours. The mixture was diluted with ethyl acetate, and the organic phase was washed with 2 N hydrochloric acid, a saturated sodium bicarbonate solution and a saturated saline solution. The resulting product was dried over sodium sulfate anhydrous and then concentrated under reduced pressure. 1,4-Dioxane (14 ml) and 1 N sodium hydroxide solution (14 ml) were added to the above compound and stirred for 17 hours at 40C. The mixture was acidified by 2 N hydrochloric acid and extracted with chloroform. The extract was dried over sodium sulfate anhydrous and then concentrated under reduced pressure. Precipitates were collected by filtration, washed with n-hexane and dried under reduced pressure to give the title compound (296 mg, Y.: 55%). 1H NMR; (DMSO-d6) delta (ppm): 3.8 (1H, s), 6.5 (1H, d), 7.1 (1H, t), 7.4 (1H, d), 7.5 (1H, dd), 7. 7 (1H, dd). ESI/MS (m/z): 176 (M+H)+, 174 (M-H)-. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20℃; for 0.5h; | Step 1 : methyl l-[3-(trifluoromethyl)benzyl]-lH-indole-7-carboxylate; Methyl lH-indole-7-carboxylate (Ig, 5.71mmol) and l-(bromomethyl)-3-(trifluoromethyl)benzene (956ul, 6.28mmol) were dissolved in DMF (16ml), in an ice bath. 60percent w/w NaH (251mg, 6.28mmol) was added portionwise. The ice bath was removed and the mixture stirred at RT for 30min. The reaction mixture was quenched with NH4Cl(SaL) and <n="24"/>extracted 3 times with ether. The organic layers were combined, washed with water and brine. The compound was purified by flash chromatography on silica gel. IH NMR (500 MHz, DMSO- d6): delta 7.40 (d, IH), 7.25 (s, IH), 7.10 (m, IH), 7.00 (m, 2H), 6.75 (s, IH), 6.65 (t, IH), 6.50 (d, IH), 6.25 (s, IH), 5.25 (s, 2H), 2.05 (d, 3H). |
[ 945655-38-9 ]
Ethyl 6-amino-2-phenyl-1H-indole-3-carboxylate
Similarity: 0.89
[ 312973-24-3 ]
Methyl 3-formyl-1H-indole-7-carboxylate
Similarity: 0.88
[ 26000-33-9 ]
Methyl 9H-carbazole-2-carboxylate
Similarity: 0.88
[ 945655-38-9 ]
Ethyl 6-amino-2-phenyl-1H-indole-3-carboxylate
Similarity: 0.89
[ 312973-24-3 ]
Methyl 3-formyl-1H-indole-7-carboxylate
Similarity: 0.88
[ 1011-65-0 ]
Methyl 1H-indole-5-carboxylate
Similarity: 0.87
[ 50820-65-0 ]
Methyl 1H-indole-6-carboxylate
Similarity: 0.87