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CAS No. : | 23145-19-9 | MDL No. : | MFCD01413839 |
Formula : | C10H8O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OPAYERWEZXLSFC-UHFFFAOYSA-N |
M.W : | 176.17 | Pubchem ID : | 31663 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.1 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 48.09 |
TPSA : | 39.44 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.89 cm/s |
Log Po/w (iLOGP) : | 1.77 |
Log Po/w (XLOGP3) : | 2.09 |
Log Po/w (WLOGP) : | 2.25 |
Log Po/w (MLOGP) : | 0.57 |
Log Po/w (SILICOS-IT) : | 2.51 |
Consensus Log Po/w : | 1.84 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.63 |
Solubility : | 0.414 mg/ml ; 0.00235 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.55 |
Solubility : | 0.499 mg/ml ; 0.00283 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.36 |
Solubility : | 0.0769 mg/ml ; 0.000437 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.06 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
57% | With potassium fluoride; N,N-dimethylammonium chloride In xylene for 24h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With acetic acid Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With manganese(IV) oxide In ethyl acetate at 20℃; for 26h; | 1004.B Step B A mixture of the product from Step A above (0.9 g), EtOAc (50 mL) and MN02 (5.2 g) was stirred at RT for 22 h, then filtered and concentrated in vacuo. The solid was REDISSOLVED in EtOAc (50 mL), MN02 (5.2 g) was added and the mixture was stirred for 4 additional hrs. Filtration, concentration and silica gel purification (EtOAc- Hexane, 1: 3) gave the title compound as a solid (0.60 g, 67%). |
67% | With manganese(IV) oxide In ethyl acetate at 20℃; for 26h; | 1004.B STEP B A mixture of the product from Step A above (0.9 g), EtOAc (50 mL) and [MN02] [(5.] 2 g) was stirred at RT for 22 h, then filtered and concentrated in vacuo. The solid was [REDISSOLVED IN] EtOAc (50 mL), [MN02] [(5.] 2 g) was added and the mixture was stirred for 4 additional hrs. Filtration, concentration and silica gel purification (EtOAc- Hexane, 1: 3) gave the title compound as a solid (0.60 g, 67%). |
67% | With manganese(IV) oxide In ethyl acetate at 20℃; for 26h; | 1004.B A mixture of the product from Step A above (0.9 g), EtOAc (50 mL) and Mn02 (5.2 g) was stirred at RT for 22 h, then filtered and concentrated in vacuo. The solid was redissolved in EtOAc (50 mL), Mn02 (5.2 g) was added and the mixture was stirred for 4 additional hrs. Filtration, concentration and silica gel purification (EtOAc- Hexane, 1: 3) gave the title compound as a solid (0.60 g, 67%). |
60% | With manganese(IV) oxide In ethyl acetate for 3h; Ambient temperature; | |
B 5-methoxybenzofurancarboxaldehyde, E9 Step (B) 5-methoxybenzofurancarboxaldehyde, E9 To a solution of 5-methoxy-2-hydroxymethylbenzofuran (16.0 gm; 90 mmoles) in ethyl acetatel (1 L) was added MnO2 (78 gm, 900 mmoles). The reaction mixture was stirred at room temperature for 3 hours. Then this suspension was filtered through celite and concentrate in vacuo. The filtrate yielded the title Compound E9, (9.5 gm, 60%). 1 H NMR w: 3.85 (s, 3H); 7.15 (m, 2H); 7.45 (m, 2H, olefinic +1 aromatic); 9.8 (s, 1H aldehyde portion). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With pyridine at 100℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | Stage #1: benzyltriphenylphosphonium bromide With lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 0.5h; Stage #2: 5-methoxy-1-benzofuran-2-carbaldehyde In tetrahydrofuran for 0.333333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
24% | Stage #1: 1-(2'-chlorobenzyl)triphenylphosphonium bromide With lithium diisopropyl amide In tetrahydrofuran; cyclohexane at 20 - 50℃; for 1.25h; Stage #2: 5-methoxy-1-benzofuran-2-carbaldehyde In tetrahydrofuran; cyclohexane for 5h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With sodium tetrahydroborate In ethanol; chloroform at 30 - 40℃; for 1h; | |
85% | With sodium tetrahydroborate; ethanol at 0 - 20℃; | (5-methoxybenzofuran-2-yl)methanol (25); Compound 24 (3.5 g, 19.9 mmol) was dissolved in EtOH (20 ml_). NaBH4 (957 mg,25.87 mmol) was added portionwise at 0 0C, with vigorous stirring. The suspension was stirred at 0 0C for 15 min and then at room temperature for 1.5 h. Solvent was evaporated off in-vacuo. The residue was adsorbed on silica gel and purified by flash chromatography, eluting with hexane/EtOAc (2:1 ) to give 25 (3.0 g, 85%) as a white solid. 1H NMR (500MHz, CDCI3): δ: 7.36 (1 H, d, J= 8.90 Hz, H-7), 7.02 (1 H, d, J = 2.6,H-4), 6.90 (1 H, dd, J = 6.30 &; 2.60, H-6), 6.61 (1 H, s, H-3), 4.76 (2H, s, 2-CH2), 3.86(3H, s, OCH3), 2.16 (1 H, bs, OH). 13C NMR CDEPT 135, (500MHz, CDCI3): δ: 113.07 (C-7), 111.69 (C-6), 104.34 (C-4), 103.60 (C-3), 58.24 (CH2), 55.92 (OCH3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 90 percent / NaBH4 / ethanol; CHCl3 / 1 h / 30 - 40 °C 2: 81 percent / dimethylformamide / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / 20 °C 1.2: 89 percent / tetrahydrofuran / 0.33 h 2.1: SnCl2 / toluene / 3 h / 125 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / 20 °C 1.2: 89 percent / tetrahydrofuran / 0.33 h 2.1: SnCl2 / toluene / 3 h / 125 °C 3.1: 53 percent / MnO2 / dioxane / 16 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / 20 °C 1.2: 89 percent / tetrahydrofuran / 0.33 h 2.1: SnCl2 / toluene / 3 h / 125 °C 3.1: 53 percent / MnO2 / dioxane / 16 h / Heating 4.1: 100 percent / BBr3 / CH2Cl2 / 2.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: LDA / tetrahydrofuran; cyclohexane / 1.25 h / 20 - 50 °C 1.2: 24 percent / cyclohexane; tetrahydrofuran / 5 h / Heating 2.1: SnCl2 / toluene / 3 h / 125 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: LDA / tetrahydrofuran; cyclohexane / 1.25 h / 20 - 50 °C 1.2: 24 percent / cyclohexane; tetrahydrofuran / 5 h / Heating 2.1: SnCl2 / toluene / 3 h / 125 °C 3.1: MnO2 / dioxane / 16 h / Heating 4.1: 89 percent / BBr3 / CH2Cl2 / 2.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: LDA / tetrahydrofuran; cyclohexane / 1.25 h / 20 - 50 °C 1.2: 24 percent / cyclohexane; tetrahydrofuran / 5 h / Heating 2.1: SnCl2 / toluene / 3 h / 125 °C 3.1: MnO2 / dioxane / 16 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1.) NaOEt / 1.) 0 deg C, 30 min, 2.) 0 deg C, 3 h 2: 76 percent / BBr3 / CH2Cl2 / 1 h / -78 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 1.) NaOEt / 1.) 0 deg C, 30 min, 2.) 0 deg C, 3 h 2: 76 percent / BBr3 / CH2Cl2 / 1 h / -78 °C 3: 53 percent / triethylsilane / tetrahydrofuran / 1 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 1.) NaOEt / 1.) 0 deg C, 30 min, 2.) 0 deg C, 3 h 2: 76 percent / BBr3 / CH2Cl2 / 1 h / -78 °C 3: 53 percent / triethylsilane / tetrahydrofuran / 1 h / Ambient temperature 4: 1.) phenylboronic acid, propionic acid, 2.) AlCl3, tert-butylamine-borane / 1.) toluene, reflux, 4 h, 2.) CH2Cl2, 0 deg C, 2 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / dimethylformamide 2: acetic acide / Heating | ||
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 4 h / Reflux 2: acetic acid / 24 h / Reflux | ||
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 150 °C 2: acetic acid / 24 h / Reflux |
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide 2: lithium hexamethyldisilazane / tetrahydrofuran 3: lithium aluminium tetrahydride / diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 87 percent 2: trimethylbenzyl ammonium hydroxide 3: hydrogen / Raney nickel / ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 87 percent 2: trimethylbenzyl ammonium hydroxide 3: hydrogen / Raney nickel / ethanol 4: 72 percent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 87 percent 2: trimethylbenzyl ammonium hydroxide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 87 percent 2: trimethylbenzyl ammonium hydroxide 3: hydrogen / Raney nickel / ethanol 4: 72 percent 5: 96 percent / ethanol / 20 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: 87 percent 2: trimethylbenzyl ammonium hydroxide 3: hydrogen / Raney nickel / ethanol 4: 72 percent 5: 96 percent / ethanol / 20 h / Heating 6: 84 percent / boron tribromide / CH2Cl2 / 12 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With acetic acid for 24h; Reflux; | General procedures for the synthesis of substitutedBenzo[b]furan-2-yl carboxaldehydes 4a-g: Method C General procedure: A stirred solution of compounds 3 (0.1 mol) in 35 mL ofconcentrated acetic acid was refluxed for 24 h. After cooling,the solution was evaporated to dryness. The crude productwas distilled or recrystallized from an appropriate solvent. |
70% | With acetic acid for 24h; Reflux; | |
24% | With acetic acid for 16h; Reflux; | 5-methoxybenzofuran-2-carbaldehyde (24); A stirred solution of 23 (1.0 g, 3.74 mmol) in acetic acid (10 ml_) was refluxed for 16 h. After cooling, the solution was evaporated to dryness. The crude product was adsorbed on silica gel and purified by flash chromatography, eluting with hexane/EtOAc (4:1 ) to give 24 (160 mg, 24%) as a white solid. 1H NMR (500MHz, CDCI3): δ: 9.80 (1 H, s, CHO), 7.49-7.45 (2H, m, ArH), 7.12-7.09 (2H, m, ArH), 3.85 (3H, s, OCH3). |
With acetic acid for 24h; Reflux; | General procedure: A solution of compounds 3aeg (0.1 mol) in 35 ml of concentratedacetic acid was refluxed for 24 h. After cooling to roomtemperature, the mixture was evaporated to dryness. The crudeproduct was distilled or recrystallized from an appropriate solvent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: lithium hexamethyldisilazane / tetrahydrofuran 2: lithium aluminium tetrahydride / diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 5-methoxy-1-benzofuran-2-carbaldehyde; anthranilic acid amide With pyridine; dmap Stage #2: With potassium hydroxide In ethanol; water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | In toluene at 100℃; for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: toluene / 48 h / 100 °C 2: C41H34O2P2; copper diacetate / tetrahydrofuran; toluene / 4 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: toluene / 48 h / 100 °C 2.1: C41H34O2P2; copper diacetate / tetrahydrofuran; toluene / 4 h / 0 - 20 °C 3.1: lithium borohydride / tetrahydrofuran / 1 h / 0 - 20 °C 3.2: 4 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 15% 2: 30% | Stage #1: 4-methylbenzyltriphenylphosphonium bromide With potassium hexamethylsilazane In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Schlenk technique; Stage #2: 5-methoxy-1-benzofuran-2-carbaldehyde In tetrahydrofuran at -78 - 20℃; for 24h; Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate; acetonitrile at 20℃; for 0.0833333h; Inert atmosphere; | General procedure General procedure: To a stirred solution of 5-fluoro-3-methyl-1H-indole-2-carbaldehyde (177 mg, 1 mmol) and morpholine (96 mg, 1.1 mmol) in acetonitrile (7 mL) was added trimethylsilyl cyanide (119 mg, 1.2 mmol) followed by T3P (63 mg, 20 mol%) at ambient temperature. The reaction mixture was stirred for an approximate time and monitored by TLC. After completion of the reaction, the reaction mixture was diluted with water (10 mL) and extracted with ethyl acetate (3* 15 mL). The organic layers were combined, washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by using 100-200 mesh silica and eluting with 13%-15% ethyl acetate in n-hexane to afford pure 2-(5-fluoro-3-methyl-1H-indol-2-yl)-2-morpholinoacetonitrile as a solid (4a) in 95% (263 mg) yield. This procedure is applied to the other reactions (4b-t). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With hydrogen trititanate In neat (no solvent) at 20℃; for 0.25h; Green chemistry; | General procedure for the synthesis of α-aminophosphonates (4a-q) General procedure: Dialkyl/diaryl phosphite (1.0 mmol) was added portion wise over a period of 5 min to the stirred mixture of heterocyclic aldehyde (1.0 mmol) and benzothiazole amine (1.0 mmol) at room temperature. Further 5 mol % of TNT was added to the reaction mixture and the stirring was continued for 15 min. After the completion of the reaction as monitored through TLC, the reaction mixture was dissolved in EtOAc (2 mL) and the catalyst was separated by centrifugation followed by subsequent washings with EtOAc. The recovered catalyst was reused for the next cycle. The filtrate was washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated on a rotary evaporator and the resulting residue was purified by silica gel column chromatography (70:30, hexane/EtOAc) to afford the corresponding pure α-aminophosphonate. The novel α-aminophosphonates were structurally assigned by their IR, NMR (1H, 13C & 31P), and mass spectral (HRMS) analyses. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With hydrogen trititanate In neat (no solvent) at 20℃; for 0.25h; Green chemistry; | General procedure for the synthesis of α-aminophosphonates (4a-q) General procedure: Dialkyl/diaryl phosphite (1.0 mmol) was added portion wise over a period of 5 min to the stirred mixture of heterocyclic aldehyde (1.0 mmol) and benzothiazole amine (1.0 mmol) at room temperature. Further 5 mol % of TNT was added to the reaction mixture and the stirring was continued for 15 min. After the completion of the reaction as monitored through TLC, the reaction mixture was dissolved in EtOAc (2 mL) and the catalyst was separated by centrifugation followed by subsequent washings with EtOAc. The recovered catalyst was reused for the next cycle. The filtrate was washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated on a rotary evaporator and the resulting residue was purified by silica gel column chromatography (70:30, hexane/EtOAc) to afford the corresponding pure α-aminophosphonate. The novel α-aminophosphonates were structurally assigned by their IR, NMR (1H, 13C & 31P), and mass spectral (HRMS) analyses. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With hydrogen trititanate In neat (no solvent) at 20℃; for 0.25h; Green chemistry; | General procedure for the synthesis of α-aminophosphonates (4a-q) General procedure: Dialkyl/diaryl phosphite (1.0 mmol) was added portion wise over a period of 5 min to the stirred mixture of heterocyclic aldehyde (1.0 mmol) and benzothiazole amine (1.0 mmol) at room temperature. Further 5 mol % of TNT was added to the reaction mixture and the stirring was continued for 15 min. After the completion of the reaction as monitored through TLC, the reaction mixture was dissolved in EtOAc (2 mL) and the catalyst was separated by centrifugation followed by subsequent washings with EtOAc. The recovered catalyst was reused for the next cycle. The filtrate was washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated on a rotary evaporator and the resulting residue was purified by silica gel column chromatography (70:30, hexane/EtOAc) to afford the corresponding pure α-aminophosphonate. The novel α-aminophosphonates were structurally assigned by their IR, NMR (1H, 13C & 31P), and mass spectral (HRMS) analyses. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With hydrogen trititanate; In neat (no solvent); at 20℃; for 0.25h;Green chemistry;Catalytic behavior; | General procedure: Dialkyl/diaryl phosphite (1.0 mmol) was added portion wise over a period of 5 min to the stirred mixture of heterocyclic aldehyde (1.0 mmol) and benzothiazole amine (1.0 mmol) at room temperature. Further 5 mol percent of TNT was added to the reaction mixture and the stirring was continued for 15 min. After the completion of the reaction as monitored through TLC, the reaction mixture was dissolved in EtOAc (2 mL) and the catalyst was separated by centrifugation followed by subsequent washings with EtOAc. The recovered catalyst was reused for the next cycle. The filtrate was washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated on a rotary evaporator and the resulting residue was purified by silica gel column chromatography (70:30, hexane/EtOAc) to afford the corresponding pure alpha-aminophosphonate. The novel alpha-aminophosphonates were structurally assigned by their IR, NMR (1H, 13C & 31P), and mass spectral (HRMS) analyses. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetic acid / 24 h / Reflux 2: hydrazine hydrate / ethanol / 2 h / Reflux | ||
Multi-step reaction with 2 steps 1: acetic acid; hydrogenchloride / 24 h / 20 °C 2: hydrazine hydrate / ethanol / 2 h / Reflux | ||
Multi-step reaction with 2 steps 1: acetic acid / 24 h / Reflux 2: hydrazine hydrate / ethanol / 2 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With acetic acid for 24h; Reflux; | General procedures for the synthesis of substituted3-benzo[b]furan-2-ylmethylene-levulinic acids 5a-g:Method D A stirred solution of compounds 4 (0.1 mol) in 35 mL ofconcentrated acetic acid was refluxed for 24 h. Aftercooling, the solution was evaporated to dryness. Theobtained residue was used crude for the continuation. | |
With hydrogenchloride; acetic acid at 20℃; for 24h; | General procedure: To a solution of appropriate aromatic aldehyde 4aeg (0.05 mol)and levulinic acid (0.06 mol) were dissolved into 20 ml ofconcentrated acetic acid and saturated with dry hydrogen chloride.Then, the mixture was stirred for 24 h at room temperature. Theprecipitate which was formed was filtered off and washed withethyl ether. The crude acids were recrystallized from an ethylacetate. | |
With acetic acid for 24h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: sodium hydroxide / 2 h / Reflux 2: potassium carbonate / N,N-dimethyl-formamide / 4 h / Reflux 3: acetic acid / 24 h / Reflux | ||
Multi-step reaction with 3 steps 1: sodium hydroxide / 2 h / 65 °C 2: potassium carbonate / N,N-dimethyl-formamide / 4 h / 150 °C 3: acetic acid / 24 h / Reflux | ||
Multi-step reaction with 3 steps 1: sodium hydroxide; water / 2.25 h / Reflux 2: potassium carbonate / N,N-dimethyl-formamide / 4 h / Reflux 3: acetic acid / 24 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With acetic acid; In methanol; at 20℃; for 72h; | 5-Methoxy-l-benzofuran-2-carbaldehyde (300 mg, 1.70 mmol) and 2- aminoisonicotinonitrile (203 mg, 1.70 mmol) were dissolved in methanol (10 mL). Acetic acid (1 mL) and methyl isocyanide (76 mu, 1.70 mmol) were added and the mixture stirred at room temperature. After 3 days the reaction mixture was filtered and the yellow precipitate washed with methanol (3 x 10 mL) and dried under suction to give the title compound 256 mg (46percent yield) as an orange powder. deltaEtaNMR (500 MHz, DMSO) 8.41 (d, J = 7.15 Hz, 1H), 8.22 (br. s, 1H), 7.54 (d, J = 8.89 Hz, 1H), 7.25 (s, 1H), 7.20 (d, J = 2.56 Hz, 1H), 7.18 (dd, J = 1.56, 7.15 Hz, 1H), 6.91 (dd, J = 2.61, 8.89 Hz, 1H), 5.43 (q, J = 5.44 Hz, 1H), 3.81 (s, 3H), 2.89 (d, J = 5.46 Hz, 3H). Tr(METCR1278) = 1.94 min, (ES+) (M+H)+ 319. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | With acetic acid In methanol at 20℃; for 18h; | teri-Butyl N-[2-(5-methoxy-l-benzofuran-2-yl)-3- (methylamino)imidazo [l,2-]pyridin-7-yl] methyl}carbamate 5-Methoxy-l-benzofuran-2-carbaldehyde (200 mg, 1.13 mmol) and tert-butyl N-[(2-aminopyridin-4-yl)methyl]carbamate (253 mg, 1.14 mmol) were suspended in methanol (5 mL). Acetic acid (0.5 mL) and methyl isocyanide (59 μ, 1.13 mmol) were added and the mixture stirred at room temperature for 18 hours. The reaction mixture was quenched with 1 M hydrochloric acid (2 mL) and stirred at room temperature for 10 minutes. The organic solvents were removed in vacuo and the aqueous neutralised with saturated aqueous sodium bicarbonate. The solution was extracted with ethyl acetate (3 x 10 mL). The combined organic extracts were washed with brine (2 x 10 mL), dried, filtered and concentrated. Purification by FCC (silica, 25-100% ethyl acetate in heptane) gave the title compound 153 mg (31% yield) as a yellow powder. Tr(MET-uHPLC-AB-lOl) = 2.38 min, (ES+) (M+H)+ 423, 92%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With piperidine In methanol at 60℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With piperidine In methanol at 60℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89.3% | With lithium aluminium tetrahydride In diethyl ether | 7 Step 7 The compound 10 (5.68 g) was caused to react with lithium aluminum hydride (LAH) under diethyl ether (Et2O) to obtain a compound 11 in the form of yellow solid (yield amount: 3.80 g, yield percentage: 89.3%). |
89.3% | With lithium aluminium tetrahydride In diethyl ether | 7 Step 7 The compound 10 (5.68 g) was caused to react with lithium aluminum hydride (LAH) under diethyl ether (Et2O) to obtain a compound 11 in the form of yellow solid (yield amount: 3.80 g, yield percentage: 89.3%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: piperidine; pyridine 2: Dess-Martin periodane; tetraethylammonium bromide / dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: piperidine; pyridine 2: Dess-Martin periodane; tetraethylammonium bromide / dichloromethane 3: triethylamine; triphenylphosphine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: piperidine; pyridine 2: Dess-Martin periodane; tetraethylammonium bromide / dichloromethane 3: triethylamine; triphenylphosphine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran 4: trifluoroacetic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96.5% | With piperidine; pyridine | 8 Step 8 Under pyridine, the compound 11 (3.69 g) was caused to react with malonic acid and piperidine to obtain a compound 12 in the form of pale yellow solid (yield amount: 4.41 g, yield percentage: 96.5%) |
96.5% | With piperidine; pyridine | 8 Step 8 Under pyridine, the compound 11 (3.69 g) was caused to react with malonic acid and piperidine to obtain a compound 12 in the form of pale yellow solid (yield amount: 4.41 g, yield percentage: 96.5%) |
[ 53860-74-5 ]
6-Methoxybenzofuran-2-carbaldehyde
Similarity: 0.98
[ 64418-91-3 ]
5-Hydroxybenzofuran-2-carbaldehyde
Similarity: 0.93
[ 88234-77-9 ]
7-Methoxybenzofuran-2-carbaldehyde
Similarity: 0.92
[ 913654-89-4 ]
6-Hydroxybenzofuran-2-carbaldehyde
Similarity: 0.91
[ 53860-74-5 ]
6-Methoxybenzofuran-2-carbaldehyde
Similarity: 0.98
[ 88234-77-9 ]
7-Methoxybenzofuran-2-carbaldehyde
Similarity: 0.92
[ 53860-74-5 ]
6-Methoxybenzofuran-2-carbaldehyde
Similarity: 0.98
[ 64418-91-3 ]
5-Hydroxybenzofuran-2-carbaldehyde
Similarity: 0.93
[ 88234-77-9 ]
7-Methoxybenzofuran-2-carbaldehyde
Similarity: 0.92
[ 913654-89-4 ]
6-Hydroxybenzofuran-2-carbaldehyde
Similarity: 0.91