Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 885273-73-4 | MDL No. : | MFCD04114770 |
Formula : | C13H16N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DVDFTRSGEMTSAL-UHFFFAOYSA-N |
M.W : | 232.28 | Pubchem ID : | 40425153 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
97% | With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 18h; | 31 Synthesis of tert-Butyl 1H-indol-6-ylcarbamate (compound 64-2) Synthesis of tert-Butyl 1H-indol-6-ylcarbamate (compound 64-2)[0000222] To a stirred solution of 1H-indol-6-amine (1.12 g, 8.5 mmol, 1 equiv) was added di-tert-butyl dicarbonate (1.95 g, 8.9 mmol, 1.05 equiv) in tetrahydrofuran (6 mL) . Saturated aqueous sodium bicarbonate (6 mL) was added and the reaction was stirred at room temperature for 18 hours. The layers were separated and the aqueous layer was extracted with ethyl acetate (3 x 5 mL) . The organic layers were combined, dried over sodium sulfate and concentrated under reduced pressure to give compound 64-2 as a white solid (2.2 g, 97% yield) |
92% | With sodium hydrogencarbonate In tetrahydrofuran at 20℃; for 16h; Inert atmosphere; | |
82% | With sodium hydroxide In diethyl ether at 20℃; |
77% | With sodium hydrogencarbonate In tetrahydrofuran; water at 30℃; for 18h; | 126.a (S)-N-(1H-lndol-6-yl)-N-methyl-3-(6-methyl-4-(trifluoromethyl)pyridin-2-yl)-2- oxooxazolidine-4-carboxamide Step a. To a stirred solution of 1H-indol-6-amine (1.12 g, 8.47 mmol) in THF (6 ml_) was added (Boc)20 (1.94 g, 8.90 mmol) followed by sat. aq. NaHCC>3 (6 ml_) and the reaction was stirred at 30°C for 18 h. Upon completion, the mixture was quenched with water (30 ml_) and extracted with EtOAc (30 ml_ x 2). The combined organic layers were washed with brine (30 ml_), dried over Na2SC>4 and evaporated. The residue was purified by column chromatography (20% EtOAc in PE) to give tert-butyl 1 H-indol-6-yl-carbamate (1.6 g, 77% yield) as a white solid. m/z ES+ [M+Na]+255.0;1H NMR (400 MHz, DMSO-d6) d ppm 10.93 (s, 1H), 9.20 (s, 1H), 7.74 (s, 1 H), 7.41 (d, J = 8.4 Hz, 1 H), 7.29 - 7.22 (m, 1 H), 7.04 (dd, = 1.6, 8.4 Hz, 1 H), 6.36(t, J = 2.0 Hz, 1 H), 1.54 (s, 9H). |
With sodium hydroxide In 1,4-dioxane at 0℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzoyl chloride; silver nitrate In acetonitrile at -10 - 25℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: benzoyl chloride; silver nitrate / acetonitrile / -10 - 25 °C 2: nitric acid / dichloromethane / 0 - 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: pyridine / 1,4-dioxane / 0.08 h / 50 °C / Microwave irradiation 2: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 50 °C / Microwave irradiation 3: trifluoroacetic acid / dichloromethane / 2 h / 0 - 20 °C 4: pyridine / dichloromethane / 0 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: diethyl ether / 2 h / 0 - 20 °C 2.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 0.5 h / 20 °C 2.2: 2 h / 20 °C 3.1: trifluoroacetic acid / dichloromethane / 2 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: diethyl ether / 2 h / 0 - 20 °C 2.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 0.5 h / 20 °C 2.2: 2 h / 20 °C 3.1: trifluoroacetic acid / dichloromethane / 2 h / 0 - 20 °C 4.1: pyridine / dichloromethane / 0 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: pyridine / 1,4-dioxane / 0.08 h / 50 °C / Microwave irradiation 2: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 50 °C / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: diethyl ether / 2 h / 0 - 20 °C 2.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 0.5 h / 20 °C 2.2: 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: pyridine / 1,4-dioxane / 0.08 h / 50 °C / Microwave irradiation 2: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 50 °C / Microwave irradiation 3: trifluoroacetic acid / dichloromethane / 2 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
16% | With pyridine In 1,4-dioxane at 50℃; for 0.0833333h; Microwave irradiation; | |
With pyridine In 1,4-dioxane at 50℃; for 0.0833333h; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With iodine; potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3h; | 31 Synthesis of tert-Butyl 3-iodo-1H-indol-6-ylcarbamate (compound 64-3) Synthesis of tert-Butyl 3-iodo-1H-indol-6-ylcarbamate (compound 64-3)[0000223] To a solution of compound 64-2 (2.3 g, 10 mmol, 1 equiv) in dimethyl formamide (10 mL) was added potassium carbonate powder (3.5g, 25 mmol, 2.5 equiv) followed by a solution of iodine (2.7g, 10.5 mmol, 1.05 equiv) in dimethyl formamide (10 mL) . The reaction was stirred at room temperature for 3 h and then poured into saturated brine (200 mL) and methyl tert-butyl ether (100 mL) . The layers were separated and the aqueous phase was extracted with methyl tert-butyl ether (3 x 50 mL) . The organic layers were combined, back extracted with brine (3 x 100 mL), and dried over sodium sulfate. The extracts were filtered and concentrated under reduced pressure to give compound 64-3 as a yellow solid (3.5g, 99% yield) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: iodine; potassium carbonate / N,N-dimethyl-formamide / 3 h / 20 °C 2: dmap; triethylamine / dichloromethane / 18 h / 20 °C / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: iodine; potassium carbonate / N,N-dimethyl-formamide / 3 h / 20 °C 2.1: dmap; triethylamine / dichloromethane / 18 h / 20 °C / Reflux 3.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 3 h / Inert atmosphere; Reflux 3.2: 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: iodine; potassium carbonate / N,N-dimethyl-formamide / 3 h / 20 °C 2.1: dmap; triethylamine / dichloromethane / 18 h / 20 °C / Reflux 3.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 3 h / Inert atmosphere; Reflux 3.2: 20 °C 4.1: sodium tetrahydroborate; acetic acid / methanol / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: pyridine / 1,4-dioxane / 0.08 h / 50 °C / Microwave irradiation 2: potassium carbonate / N,N-dimethyl-formamide / 0.08 h / 50 °C / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: diethyl ether / 2 h / 0 - 20 °C / Inert atmosphere 2.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 0.5 h / 20 °C 2.2: 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: pyridine / 1,4-dioxane / 0.08 h / 50 °C / Microwave irradiation 2: potassium carbonate / N,N-dimethyl-formamide / 0.08 h / 50 °C / Microwave irradiation 3: trifluoroacetic acid / dichloromethane / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: diethyl ether / 2 h / 0 - 20 °C / Inert atmosphere 2.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 0.5 h / 20 °C 2.2: 2 h / 20 °C 3.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: pyridine / 1,4-dioxane / 0.08 h / 50 °C / Microwave irradiation 2: potassium carbonate / N,N-dimethyl-formamide / 0.08 h / 50 °C / Microwave irradiation 3: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 4: pyridine / dichloromethane / 20 h / 0 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: diethyl ether / 2 h / 0 - 20 °C / Inert atmosphere 2.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 0.5 h / 20 °C 2.2: 2 h / 20 °C 3.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 4.1: pyridine / dichloromethane / 20 h / 0 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In diethyl ether at 0 - 20℃; for 2h; Inert atmosphere; | 3.1.3. General procedure for the synthesis of compounds 29 and 32-34 General procedure: To a solution of appropriate intermediates 10-12 (1 mmol) in diethyl ether (5 mL) the oxalyl chloride (0.173 mL, 2 mmol) was added slowly at 0 °C under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 2 h. A saturated aqueous NaHCO3 solution (5 mL) was added to quench the reaction and the mixture was extracted with EtOAc (3 x 10 mL). The combined extracts were dried with dry Na2SO4 and concentrated in vacuo. A mixture of crude compounds (20-22) (1 mmol) and N,N,N,N-tetramethyl- O-(1H-benzotriazol-1-yl)uronium hexafluorophosphate (HBTU) (379 mg, 1 mmol) in dimethylformamide (2 mL) was stirred for 30 min at room temperature. Successively, 4-benzylpiperidine (0.175 mL, 1 mmol) or 4-fluorobenzylpiperidine (193.3 mg, 1 mmol) and TEA (0.139 mL, 1 mmol) were added, the reaction mixture was stirred for 2 h at room temperature. Then the reaction mixture was quenched with H2O (10 mL) and extracted with EtOAc (3 x x10 mL). The combined extracts were dried with dry Na2SO4 and concentrated in vacuo. The crude compounds were purified by flash chromatography (FC) (DCM/MeOH 96:4) and recrystallized by treatment with Et2O to give the desired final products 29, 32-34. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With dmap; triethylamine In dichloromethane at 20℃; for 95h; | tert-Butyl 6-[bis(tert-butoxycarbonyl)amino]indoleA -carboxylate (Intermediate 63) To a solution of te/f-butyl A/-(1 /-/-indol-6-yl)carbamate (760 mg, 3.17 mmol) in DCM (15 ml_) was added Boc20 (1.70 g, 7.79 mmol), Et3N (1.20 ml_, 8.61 mmol) and DMAP (35.0 mg, 0.290 mmol) and the resulting mixture stirred at room temperature for 71 h. Further B0C2O (850 mg, 3.90 mmol) and EtzN (600 μΙ_, 4.31 mmol) was added and the mixture stirred for a further 24 h. The solvent was concentrated in vacuo and the crude product purified by fee (0-20% EtOAc in isohexane) to return the title compound (1.35 g, 98%) as a colourless gum. LCMS [M+Na]+ 455; 1 H NMR (400MHz, DMSO-cfe) δ 7.81 (s, 1 H), 7.72 (d, J = 3.7 Hz, 1 H), 7.61 (d, J = 8.3 Hz, 1 H), 7.05 (dd, J = 8.3, 2.0 Hz, 1 H), 6.74 (d, J = 4.5 Hz, 1 H), 1.62 (s, 9H), 1.41 (s, 18H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: carbon dioxide; tert-butyl N-(1H-indol-6-yl)carbamate With lithium tert-butoxide In N,N-dimethyl-formamide at 100℃; for 24h; Stage #2: methanol With thionyl chloride at 0℃; for 2h; Reflux; Stage #3: With palladium 10% on activated carbon; hydrogen In methanol for 2h; Inert atmosphere; | 15 Methyl 6-((tert-butoxycarbonyl)amino)indoline-3-carboxylate tert-Butyl (1H-indol-6-yl)carbamate (1 equiv.) is dissolved in dry N,N- dimethylformamide. Lithium tert-butoxide (5 equiv.) is added. Carbon dioxide is bubbled through the solution which is then heated to 100 °C. After 24 h, the reaction is cooled to room temperature and quenched with saturated ammonium chloride aqueous solution. The mixture is diluted with ethyl acetate and the organic layer is separated. The aqueous layer is extracted with ethyl acetate (3 x) and the combined organic layers are washed with brine and dried over sodium sulfate before concentrating. The resulting carboxylic acid is then dissolved in methanol and cooled to 0 °C. Thionyl chloride (1 equiv.) is added slowly. The reaction mixture is heated to reflux for 2 hours. It is then cooled to room temperature and diluted with ice water. The mixture is extracted with ethyl acetate (3 x) and the combined organic layers are washed with saturated sodium bicarbonate solution and then brine before drying with sodium sulfate. The mixture is concentrated and purified on silica to provide the desired methyl ester. The methyl ester is then dissolved in methanol. Palladium on carbon (10% by wt) is then added and the solution is degassed 3 times by replacing the air with nitrogen and finally the nitrogen with hydrogen. The reaction mixture was further stirred under hydrogen atmosphere for 2 h. The hydrogen gas was then purged and the mixture was filtered through a pad of celite and washed with methanol. The solvent was removed under vacuum and the resulting material was purified on silica to provide methyl 6-((tert-butoxycarbonyl)amino)indoline-3-carboxylate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: lithium tert-butoxide / N,N-dimethyl-formamide / 24 h / 100 °C / 760.05 Torr 1.2: 2 h / 0 °C / Reflux 1.3: 2 h / Inert atmosphere 2.2: -78 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: lithium tert-butoxide / N,N-dimethyl-formamide / 24 h / 100 °C / 760.05 Torr 1.2: 2 h / 0 °C / Reflux 1.3: 2 h / Inert atmosphere 2.2: -78 - 20 °C 3.1: acetic acid; sulfuric acid / 2 h / Reflux 3.2: 2 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: manganese(IV) oxide / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 20 °C 3: sodium hydrogencarbonate / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 20 °C 2: sodium hydrogencarbonate / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: nitric acid; sulfuric acid / 0 - 20 °C 2: manganese(IV) oxide / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere 3: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 20 °C 4: sodium hydrogencarbonate / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | In N,N-dimethyl-formamide at 150℃; for 1h; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 1 h / 150 °C / Microwave irradiation 2: trifluoroacetic acid / dichloromethane / 20 °C / Inert atmosphere 3: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 12.17 h / 20 °C / Inert atmosphere 4: 0.5 h / 150 °C / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 1 h / 150 °C / Microwave irradiation 2: trifluoroacetic acid / dichloromethane / 20 °C / Inert atmosphere 3: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 12.17 h / 20 °C / Inert atmosphere 4: 0.33 h / 150 °C / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 1 h / 150 °C / Microwave irradiation 2: trifluoroacetic acid / dichloromethane / 20 °C / Inert atmosphere 3: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 12.17 h / 20 °C / Inert atmosphere 4: 1.17 h / 150 °C / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 1 h / 150 °C / Microwave irradiation 2: trifluoroacetic acid / dichloromethane / 20 °C / Inert atmosphere 3: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 12.17 h / 20 °C / Inert atmosphere 4: 0.42 h / 150 °C / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 1 h / 150 °C / Microwave irradiation 2: trifluoroacetic acid / dichloromethane / 20 °C / Inert atmosphere 3: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 12.17 h / 20 °C / Inert atmosphere 4: 0.67 h / 150 °C / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 1 h / 150 °C / Microwave irradiation 2: trifluoroacetic acid / dichloromethane / 20 °C / Inert atmosphere 3: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 12.17 h / 20 °C / Inert atmosphere 4: 1 h / 150 °C / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 1 h / 150 °C / Microwave irradiation 2: trifluoroacetic acid / dichloromethane / 20 °C / Inert atmosphere 3: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 12.17 h / 20 °C / Inert atmosphere 4: 0.33 h / 150 °C / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 1 h / 150 °C / Microwave irradiation 2: trifluoroacetic acid / dichloromethane / 20 °C / Inert atmosphere 3: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 12.17 h / 20 °C / Inert atmosphere 4: 0.33 h / 150 °C / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 1 h / 150 °C / Microwave irradiation 2: trifluoroacetic acid / dichloromethane / 20 °C / Inert atmosphere 3: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 12.17 h / 20 °C / Inert atmosphere 4: 0.67 h / 150 °C / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: N,N-dimethyl-formamide / 1 h / 150 °C / Microwave irradiation 2: trifluoroacetic acid / dichloromethane / 20 °C / Inert atmosphere 3: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 12.17 h / 20 °C / Inert atmosphere 4: palladium diacetate; copper diacetate / acetic acid / 8 h / 100 °C / Inert atmosphere 5: 3 h / 140 °C / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: N,N-dimethyl-formamide / 1 h / 150 °C / Microwave irradiation 2: trifluoroacetic acid / dichloromethane / 20 °C / Inert atmosphere 3: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 12.17 h / 20 °C / Inert atmosphere 4: palladium diacetate; copper diacetate / acetic acid / 8 h / 100 °C / Inert atmosphere 5: 3 h / 140 °C / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: N,N-dimethyl-formamide / 1 h / 150 °C / Microwave irradiation 2: trifluoroacetic acid / dichloromethane / 20 °C / Inert atmosphere 3: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 12.17 h / 20 °C / Inert atmosphere 4: palladium diacetate; copper diacetate / acetic acid / 8 h / 100 °C / Inert atmosphere 5: 4 h / 140 °C / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 1 h / 150 °C / Microwave irradiation 2: trifluoroacetic acid / dichloromethane / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide / 1 h / 150 °C / Microwave irradiation 2: trifluoroacetic acid / dichloromethane / 20 °C / Inert atmosphere 3: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 12.17 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 1 h / 150 °C / Microwave irradiation 2: trifluoroacetic acid / dichloromethane / 20 °C / Inert atmosphere 3: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 12.17 h / 20 °C / Inert atmosphere 4: palladium diacetate; copper diacetate / acetic acid / 8 h / 100 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane / 3 h / -20 °C / Inert atmosphere 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C 2.2: 12 h / 30 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane / 3 h / -20 °C / Inert atmosphere 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C 2.2: 12 h / 30 °C 3.1: hydrogenchloride / 1,4-dioxane / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane / 3 h / -20 °C / Inert atmosphere 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C 2.2: 12 h / 30 °C 3.1: hydrogenchloride / 1,4-dioxane / 1 h / 20 °C 4.1: triethylamine / dichloromethane / 1 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane / 3 h / -20 °C / Inert atmosphere 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C 2.2: 12 h / 30 °C 3.1: hydrogenchloride / 1,4-dioxane / 1 h / 20 °C 4.1: triethylamine / dichloromethane / 1 h / 0 °C 5.1: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1 h / 100 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane / 3 h / -20 °C / Inert atmosphere 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C 2.2: 12 h / 30 °C 3.1: hydrogenchloride / 1,4-dioxane / 1 h / 20 °C 4.1: triethylamine / dichloromethane / 1 h / 0 °C 5.1: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1 h / 100 °C / Inert atmosphere 6.1: cesium fluoride / N,N-dimethyl-formamide / 12 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With tetrabutylammomium bromide; sodium hydroxide In dichloromethane at -20℃; for 3h; Inert atmosphere; | 126.b Step b. To a suspension of NaOH (1.21 g, 30 mmol) in dry DCM (7 ml_) at -20°C under N2 atmosphere was added tert-butyl 1 H-indol-6-ylcarbamate (700 mg, 3.01 mmol), TBAB (48 mg, 0.15 mmol) and p-toluenesulfonyl chloride (5.75 g, 30 mmol) sequentially. The resulting mixture was stirred under N2 atmosphere at -20°C for 3 h. Then the mixture was slowly warmed to rt and stirred for 9 h. Upon completion, the mixture was diluted with water (100 ml_), extracted with EtOAc (100 ml_ x 2). The combined organic layers were washed with brine (80 ml_), dried and evaporated. The residue was purified by column chromatography (10% EtOAc in PE) to give tert-butyl (1-tosyl-1H-indol-6-yl)carbamate (0.9 g, 77% yield) as a white solid. m/z ES+ [M+Na]+ 409.1 |