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[ CAS No. 23145-19-9 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 23145-19-9
Chemical Structure| 23145-19-9
Chemical Structure| 23145-19-9
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Product Details of [ 23145-19-9 ]

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 :

Calculated chemistry of [ 23145-19-9 ]

Physicochemical Properties

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

Pharmacokinetics

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

Lipophilicity

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

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

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

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.06

Safety of [ 23145-19-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 23145-19-9 ]

* 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.

  • Downstream synthetic route of [ 23145-19-9 ]

[ 23145-19-9 ] Synthesis Path-Downstream   1~51

  • 1
  • [ 23145-19-9 ]
  • [ 1530-39-8 ]
  • [ 139201-62-0 ]
  • 2
  • [ 23145-19-9 ]
  • [ 63909-39-7 ]
  • [ 107092-74-0 ]
YieldReaction ConditionsOperation in experiment
57% With potassium fluoride; N,N-dimethylammonium chloride In xylene for 24h; Heating;
  • 3
  • [ 23145-29-1 ]
  • [ 23145-19-9 ]
YieldReaction ConditionsOperation in experiment
With acetic acid Heating;
  • 4
  • [ 37603-26-2 ]
  • [ 23145-19-9 ]
YieldReaction ConditionsOperation 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).

  • 5
  • [ 23145-19-9 ]
  • [ 1099-45-2 ]
  • [ 88221-05-0 ]
YieldReaction ConditionsOperation in experiment
87%
  • 6
  • [ 23145-19-9 ]
  • [ 141-82-2 ]
  • (E)-3-(5-methoxy-2-benzofuranyl)-2-propenoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With pyridine at 100℃; for 1h;
  • 7
  • [ 23145-19-9 ]
  • [ 1449-46-3 ]
  • [ 622863-29-0 ]
YieldReaction ConditionsOperation 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;
  • 8
  • [ 23145-19-9 ]
  • [ 62640-67-9 ]
  • [ 622863-31-4 ]
YieldReaction ConditionsOperation 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;
  • 9
  • [ 23145-19-9 ]
  • [ 37603-26-2 ]
YieldReaction ConditionsOperation 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).
  • 10
  • [ 23145-19-9 ]
  • N,N-dimethyl-(5-methoxy-2-methylbenzofuran-3-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 90 percent / NaBH4 / ethanol; CHCl3 / 1 h / 30 - 40 °C 2: 81 percent / dimethylformamide / Heating
  • 11
  • [ 23145-19-9 ]
  • 9-methoxy-4-phenyl-3a,4,5,10c-tetrahydro-6-oxa-2-aza-cyclopenta[<i>c</i>]fluorene-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation 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
  • 12
  • [ 23145-19-9 ]
  • [ 622863-30-3 ]
YieldReaction ConditionsOperation 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
  • 13
  • [ 23145-19-9 ]
  • 9-hydroxy-4-phenyl-6-oxa-2-aza-cyclopenta[<i>c</i>]fluorene-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation 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
  • 14
  • [ 23145-19-9 ]
  • 4-(2-chloro-phenyl)-9-methoxy-3a,4,5,10c-tetrahydro-6-oxa-2-aza-cyclopenta[<i>c</i>]fluorene-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation 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
  • 15
  • [ 23145-19-9 ]
  • 4-(2-chloro-phenyl)-9-hydroxy-6-oxa-2-aza-cyclopenta[<i>c</i>]fluorene-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation 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
  • 16
  • [ 23145-19-9 ]
  • [ 622863-32-5 ]
YieldReaction ConditionsOperation 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
  • 17
  • [ 23145-19-9 ]
  • 2-<2-(4-chlorophenyl)ethenyl>-5-benzofuranol [ No CAS ]
YieldReaction ConditionsOperation 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
  • 18
  • [ 23145-19-9 ]
  • [ 138853-86-8 ]
YieldReaction ConditionsOperation 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
  • 19
  • [ 23145-19-9 ]
  • [ 138853-90-4 ]
YieldReaction ConditionsOperation 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
  • 20
  • [ 10242-08-7 ]
  • [ 23145-19-9 ]
  • 21
  • [ 672-13-9 ]
  • [ 23145-19-9 ]
YieldReaction ConditionsOperation 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

  • 22
  • [ 23145-19-9 ]
  • [ 88221-15-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 87 percent 2: trimethylbenzyl ammonium hydroxide 3: hydrogen / Raney nickel / ethanol
  • 23
  • [ 23145-19-9 ]
  • [ 88221-25-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 87 percent 2: trimethylbenzyl ammonium hydroxide 3: hydrogen / Raney nickel / ethanol 4: 72 percent
  • 24
  • [ 23145-19-9 ]
  • 3-(5-Methoxy-benzofuran-2-yl)-4-nitro-butyric acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 87 percent 2: trimethylbenzyl ammonium hydroxide
  • 25
  • [ 23145-19-9 ]
  • [ 88234-67-7 ]
YieldReaction ConditionsOperation 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
  • 26
  • [ 23145-19-9 ]
  • [ 88234-71-3 ]
YieldReaction ConditionsOperation 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
  • 27
  • [ 1254062-17-3 ]
  • [ 23145-19-9 ]
YieldReaction ConditionsOperation 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.

  • 28
  • [ 50551-56-9 ]
  • [ 23145-19-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: lithium hexamethyldisilazane / tetrahydrofuran 2: lithium aluminium tetrahydride / diethyl ether
  • 29
  • [ 23145-19-9 ]
  • [ 28144-70-9 ]
  • [ 374762-25-1 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 5-methoxy-1-benzofuran-2-carbaldehyde; anthranilic acid amide With pyridine; dmap Stage #2: With potassium hydroxide In ethanol; water
  • 30
  • [ 23145-19-9 ]
  • [ 627546-31-0 ]
  • [ 1448857-56-4 ]
YieldReaction ConditionsOperation in experiment
95% In toluene at 100℃; for 48h;
  • 31
  • [ 23145-19-9 ]
  • [ 1448857-57-5 ]
YieldReaction ConditionsOperation 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
  • 32
  • [ 23145-19-9 ]
  • [ 449727-88-2 ]
YieldReaction ConditionsOperation 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
  • 33
  • [ 23145-19-9 ]
  • [ 2378-86-1 ]
  • [ 1429509-57-8 ]
  • [ 1429509-14-7 ]
YieldReaction ConditionsOperation 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;
  • 34
  • [ 110-91-8 ]
  • [ 23145-19-9 ]
  • [ 7677-24-9 ]
  • 2-(5-methoxybenzofuran-2-yl)-2-morpholinoacetonitrile [ No CAS ]
YieldReaction ConditionsOperation 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).
  • 35
  • [ 533-30-2 ]
  • [ 23145-19-9 ]
  • [ 762-04-9 ]
  • diethyl (benzo[d]thiazol-6-ylamino)(5-methoxybenzofuran-2-yl)methylphosphonate [ No CAS ]
YieldReaction ConditionsOperation 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.
  • 36
  • [ 1809-19-4 ]
  • [ 533-30-2 ]
  • [ 23145-19-9 ]
  • dibutyl (benzo[d]thiazol-6-ylamino)(5-methoxybenzofuran-2-yl)methylphosphonate [ No CAS ]
YieldReaction ConditionsOperation 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.
  • 37
  • [ 533-30-2 ]
  • [ 23145-19-9 ]
  • [ 4712-55-4 ]
  • diphenyl(benzo[d]thiazol-6-ylamino)(5-methoxybenzofuran-2-yl)methylphosphonate [ No CAS ]
YieldReaction ConditionsOperation 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.
  • 38
  • [ 1123-93-9 ]
  • [ 23145-19-9 ]
  • [ 4712-55-4 ]
  • diphenyl (benzo[d]thiazol-5-ylamino)(5-methoxybenzofuran-2-yl)methylphosphonate [ No CAS ]
YieldReaction ConditionsOperation 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.
  • 39
  • [ 23145-19-9 ]
  • 5-(5-methoxybenzo[b]furan-2-ylmethyl)-6-methylpyridazin-3(2H)-one [ No CAS ]
YieldReaction ConditionsOperation 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
  • 40
  • [ 23145-19-9 ]
  • [ 123-76-2 ]
  • 2-formyl-5-methoxybenzo[b]furan [ No CAS ]
YieldReaction ConditionsOperation 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;
  • 41
  • [ 150-76-5 ]
  • [ 23145-19-9 ]
YieldReaction ConditionsOperation 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
  • 42
  • [ 23145-19-9 ]
  • [ 42182-27-4 ]
  • 3-(dimethylamino)-2-(5-methoxy-1-benzofuran-2-yl)imidazo[1,2-a]pyridine-7-carbonitrile [ No CAS ]
  • 43
  • [ 23145-19-9 ]
  • [ 593-75-9 ]
  • [ 42182-27-4 ]
  • 2-(5-methoxy-1-benzofuran-2-yl)-3-(methylamino)imidazo[1,2-a]pyridine-7-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation 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.
  • 44
  • [ 23145-19-9 ]
  • [ 685498-28-6 ]
  • [ 474809-21-7 ]
  • tert-butyl N-[2-(5-methoxy-1-benzofuran-2-yl)-3-(methylamino)imidazo[1,2-a]pyridin-7-yl] methyl}carbamate [ No CAS ]
YieldReaction ConditionsOperation 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%.
  • 45
  • [ 23145-19-9 ]
  • [ 1346151-06-1 ]
  • C28H30N2O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With piperidine In methanol at 60℃; for 2h;
  • 46
  • [ 23145-19-9 ]
  • 6-hydroxy-7-((3-methylpiperidin-1-yl)methyl)benzofuran-3(2H)-one [ No CAS ]
  • (Z)-6-hydroxy-2-((5-methoxybenzofuran-2-yl)methylene)-7-((3-methylpiperidin-1-yl)methyl)benzofuran-3(2H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With piperidine In methanol at 60℃; for 2h;
  • 47
  • N,5-dimethoxy-N-methyl-1-benzofuran-2-carboxamide [ No CAS ]
  • [ 23145-19-9 ]
YieldReaction ConditionsOperation 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%).
  • 48
  • [ 23145-19-9 ]
  • C11H9BrO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: piperidine; pyridine 2: Dess-Martin periodane; tetraethylammonium bromide / dichloromethane
  • 49
  • [ 23145-19-9 ]
  • C24H23FN2O4 [ No CAS ]
YieldReaction ConditionsOperation 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
  • 50
  • [ 23145-19-9 ]
  • C19H15FN2O2 [ No CAS ]
YieldReaction ConditionsOperation 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
  • 51
  • [ 23145-19-9 ]
  • [ 141-82-2 ]
  • [ 57329-45-0 ]
YieldReaction ConditionsOperation 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%)
Same Skeleton Products
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