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CAS No. : | 56317-21-6 | MDL No. : | MFCD17166969 |
Formula : | C14H10O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LHPRYOJTASOZGJ-UHFFFAOYSA-N |
M.W : | 242.23 g/mol | Pubchem ID : | 185848 |
Synonyms : |
1. Moracin M |
Num. heavy atoms : | 18 |
Num. arom. heavy atoms : | 15 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 67.72 |
TPSA : | 73.83 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -5.7 cm/s |
Log Po/w (iLOGP) : | 1.69 |
Log Po/w (XLOGP3) : | 2.92 |
Log Po/w (WLOGP) : | 3.22 |
Log Po/w (MLOGP) : | 1.2 |
Log Po/w (SILICOS-IT) : | 2.47 |
Consensus Log Po/w : | 2.3 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.73 |
Solubility : | 0.0449 mg/ml ; 0.000185 mol/l |
Class : | Soluble |
Log S (Ali) : | -4.13 |
Solubility : | 0.0179 mg/ml ; 0.0000738 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -4.08 |
Solubility : | 0.0199 mg/ml ; 0.0000822 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.81 |
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: |
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* 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 |
---|---|---|
Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With tetrabutyl ammonium fluoride In tetrahydrofuran for 48h; Ambient temperature; | |
86% | With tetrabutyl ammonium fluoride In tetrahydrofuran for 16h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 22% 2: 18% | With boron tribromide In dichloromethane for 480h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
12.3% | With formic acid for 1h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With potassium carbonate In acetone Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Oxyresveratrol-tetraacetat, 1) Br2, 2) KOH in CH3OH, 3) HOAc; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen In ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: K2CO3 / acetone 2: LAH; AlCl3 / diethyl ether; tetrahydrofuran / 1.5 h 3: 11 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 7.5 h / Heating 4: hydrogen / Pd-C / ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: LAH; AlCl3 / diethyl ether; tetrahydrofuran / 1.5 h 2: 11 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 7.5 h / Heating 3: hydrogen / Pd-C / ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 11 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 7.5 h / Heating 2: hydrogen / Pd-C / ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: KOAc / acetic anhydride / 10 h / 150 °C 2: K2CO3 / acetone 3: LAH; AlCl3 / diethyl ether; tetrahydrofuran / 1.5 h 4: 11 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 7.5 h / Heating 5: hydrogen / Pd-C / ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: KOAc / acetic anhydride / 10 h / 150 °C 2: K2CO3 / acetone 3: LAH; AlCl3 / diethyl ether; tetrahydrofuran / 1.5 h 4: 11 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 7.5 h / Heating 5: hydrogen / Pd-C / ethanol | ||
Multi-step reaction with 4 steps 1.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C 2.1: triphenylphosphine / dichloromethane / 0.75 h / 0 °C 2.2: 0.08 h / 0 °C 2.3: 14.5 h / 0 - 20 °C 3.1: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 4.1: boron tribromide / dichloromethane | ||
Multi-step reaction with 4 steps 1: dmap; triethylamine / dichloromethane 2: triphenylphosphine / dichloromethane / 14.5 h / 0 - 20 °C 3: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 4: boron tribromide / dichloromethane |
Multi-step reaction with 5 steps 1.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C 2.1: triphenylphosphine / dichloromethane / 0.75 h / 0 °C 2.2: 0.08 h / 0 °C 2.3: 14.5 h / 0 - 20 °C 3.1: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 4.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C 5.1: boron tribromide / dichloromethane / 24 h / -78 - 20 °C | ||
Multi-step reaction with 5 steps 1: dmap; triethylamine / dichloromethane 2: triphenylphosphine / dichloromethane / 14.5 h / 0 - 20 °C 3: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 4: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C 5: boron tribromide / dichloromethane / 24 h / -78 - 20 °C | ||
Multi-step reaction with 3 steps 1.1: triphenylphosphine; zinc / acetonitrile / 1 h / 20 °C / Inert atmosphere 1.2: 0.5 h / 20 °C / Inert atmosphere 2.1: caesium carbonate; copper(l) iodide / acetonitrile / 3 h / 80 °C / Inert atmosphere 3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium phosphate / water; N,N-dimethyl-formamide / 1 h / Inert atmosphere; Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1) BuLi, Me3SnCl, 2) Pd(PPh3)4 / 1) THF, rt, 1 h, 2) THF, reflux 2: 86 percent / Bu4NF / tetrahydrofuran / 16 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: trichlorophosphate / acetonitrile 2.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C 3.1: triphenylphosphine / dichloromethane / 0.75 h / 0 °C 3.2: 0.08 h / 0 °C 3.3: 14.5 h / 0 - 20 °C 4.1: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 5.1: boron tribromide / dichloromethane | ||
Multi-step reaction with 5 steps 1: trichlorophosphate / acetonitrile 2: dmap; triethylamine / dichloromethane 3: triphenylphosphine / dichloromethane / 14.5 h / 0 - 20 °C 4: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 5: boron tribromide / dichloromethane | ||
Multi-step reaction with 6 steps 1.1: trichlorophosphate / acetonitrile 2.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C 3.1: triphenylphosphine / dichloromethane / 0.75 h / 0 °C 3.2: 0.08 h / 0 °C 3.3: 14.5 h / 0 - 20 °C 4.1: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 5.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C 6.1: boron tribromide / dichloromethane / 24 h / -78 - 20 °C |
Multi-step reaction with 6 steps 1: trichlorophosphate / acetonitrile 2: dmap; triethylamine / dichloromethane 3: triphenylphosphine / dichloromethane / 14.5 h / 0 - 20 °C 4: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 5: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C 6: boron tribromide / dichloromethane / 24 h / -78 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 82 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1) sec-BuLi, N,N,N',N'-tetramethylethylenediamine / 1) cyclohexane, THF, -105 deg C, 20 min 2) THF, -105 deg C, 1h 3: 12.3 percent / 90percent HCO2H / 1 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 1) sec-BuLi, N,N,N',N'-tetramethylethylenediamine / 1) cyclohexane, THF, -105 deg C, 20 min 2) THF, -105 deg C, 1h 2: 52 percent / 90percent HCO2H / 1 h / Heating 3: 18 percent / BBr3 / CH2Cl2 / 480 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 1) sec-BuLi, N,N,N',N'-tetramethylethylenediamine / 1) cyclohexane, THF, -105 deg C, 20 min 2) THF, -105 deg C, 1h 2: 52 percent / 90percent HCO2H / 1 h / Heating 3: 18 percent / BBr3 / CH2Cl2 / 480 h / Ambient temperature | ||
Multi-step reaction with 2 steps 1: 1) sec-BuLi, N,N,N',N'-tetramethylethylenediamine / 1) cyclohexane, THF, -105 deg C, 20 min 2) THF, -105 deg C, 1h 2: 12.3 percent / 90percent HCO2H / 1 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1) sec-BuLi, N,N,N',N'-tetramethylethylenediamine / 1) cyclohexane, THF, -105 deg C, 20 min 2) THF, -105 deg C, 1h 2: 12.3 percent / 90percent HCO2H / 1 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 52 percent / 90percent HCO2H / 1 h / Heating 2: 18 percent / BBr3 / CH2Cl2 / 480 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 2: 86 percent / TBAF / tetrahydrofuran / 48 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.1 mg | In [D3]acetonitrile at 80℃; for 8h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: aluminum oxide / 5,5-dimethyl-1,3-cyclohexadiene / 16 h / Reflux 2: boron tribromide / dichloromethane / 0 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | Stage #1: 2-(3,5-dimethoxyphenyl)-6-methoxybenzofuran With boron tribromide In dichloromethane at -78 - 25℃; for 24h; Schlenk technique; Inert atmosphere; Stage #2: With water In dichloromethane Schlenk technique; Inert atmosphere; Cooling with ice; | |
70% | With boron tribromide In dichloromethane at -78 - 20℃; for 3h; Inert atmosphere; | 7-(6-Hydroxybenzofuran-2-yl)-2,2-dimethylchroman-5-ol,Wittifuran D (11): General procedure: To a stirred solutionof 8 (100 mg, 0.28 mmol) in dry DCM (4 mL) at 78 C under nitrogen conditions wasadded dropwise 1-M BBr3 solution in CH2Cl2 (1.4 mL, 1.42 mmol) and stirred at the sametemperature for 2 h, then room temperature for 1 h. After completion of the reaction, theexcess BBr3 was quenched by adding ice water at 0 C. The reaction mixture was warmedto room temperature and extracted with ethyl acetate 2 times. The combined organic layerwas dried over MgSO4, filtered, and evaporated. The residue was purified by silica gelcolumn chromatography (Hex:EtOAc = 7:3, v/v) to afford compound 11 (50 mg, 60% yield)as a white solid: |
Stage #1: 2-(3,5-dimethoxyphenyl)-6-methoxybenzofuran With boron tribromide In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere; Stage #2: With methanol In dichloromethane at 0℃; | 13 Example 13: Preparation of 5-(6-hydroxy-1-benzofuran-2-yl)benzene-1,3-diol, with the following structural formula: [Show Image]; This compound was prepared using Method A from resorcinol and 2-bromo-1-(3,5-dimethoxyphenyl)ethanone: Yield 25% following procedures A.2 and A.5; m.p. 168°C (dec.); IR 3355, 2931, 1613, 1432, 1293, 1145 cm-1; 1H-NMR (500 MHz, δ ppm, DMSO-d6) 9.52 (s, 1H), 9.37 (s, 2H), 7.38 (d, J = 8.4 Hz, 1H), 7.06 (s, 1H), 6.92 (s, 1H), 6.74 (d, J = 8.3 Hz, 1H), 6.68 (s, 2H), 6.21 (s, 1H); 13C-NMR (126 MHz, δ ppm, CD3O) 160.1, 157.4, 156.9, 156.3, 133.9, 123.2, 122.1, 113.4, 104.1, 103.7, 102.3, 98.6. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With aluminum (III) chloride In chloroform at 65℃; for 9h; | 1.4 Example 1 2- (3,5-Dimethoxyphenyl) -6-hydroxybenzofuran (10 mmol, 2.70 g), aluminum trichloride(40 mmol, 5.33 g) was added to 50 ml of chloroform, stirred, heated to 65 ° C, 9 h reaction;After completion, the solution was cooled to room temperature, filtered, washed with water (10 ml x 3), dried over anhydrous magnesium sulfate and concentrated.The alcohol was recrystallized to give 2.23 g of white Moracin M as a solid in 92% yield. |
88% | With boron tribromide In dichloromethane at -78 - 20℃; for 8h; Inert atmosphere; Schlenk technique; | |
88% | With boron tribromide In dichloromethane at -78 - 20℃; for 8h; Inert atmosphere; | 27.2 (2) Take 2- (3,5-dimethoxyphenyl) benzofuran-6-phenol (M18, 40.5mg, 0.15mmol, 1.0eq.)5 ml of dry methylene chloride was added, and boron tribromide (3.0 eq., 1 mmol / mL methylene chloride solution) was added dropwise under a nitrogen atmosphere at -78 ° C, and the reaction was raised to room temperature and stirred for 8 hours. Slowly add 2 mL of water to quench the reaction. Extracted with ethyl acetate (10mL x 3), the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, concentrated and purified by column chromatography (eluent PE / EA = 10/1) to obtain the product Moracin M (P4-3) (32mg, 88%). Characteristic data is consistent with literature data. |
86% | With aluminum (III) chloride In 1,2-dichloro-ethane at 80℃; | |
26% | With aluminum oxide In 5,5-dimethyl-1,3-cyclohexadiene for 16h; Reflux; | |
25% | With boron tribromide In dichloromethane at 0 - 20℃; Inert atmosphere; | |
25% | With boron tribromide In dichloromethane at 0℃; | |
25% | With boron tribromide In dichloromethane | |
Multi-step reaction with 2 steps 1: 1H-imidazole / tetrahydrofuran / 2 h / 20 °C 2: n-butyllithium; diphenylphosphane / tetrahydrofuran; hexane / 36 h / Inert atmosphere; Reflux | ||
Multi-step reaction with 2 steps 1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C 2: boron tribromide / dichloromethane / 24 h / -78 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: triethylamine / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: palladium diacetate; copper(l) iodide; tri tert-butylphosphoniumtetrafluoroborate / 72 h / 40 °C / Inert atmosphere 3.1: potassium hydroxide; water / methanol / 5 h / Inert atmosphere; Reflux 4.1: boron tribromide / dichloromethane / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: palladium diacetate; copper(l) iodide; tri tert-butylphosphoniumtetrafluoroborate / 72 h / 40 °C / Inert atmosphere 2: potassium hydroxide; water / methanol / 5 h / Inert atmosphere; Reflux 3: boron tribromide / dichloromethane / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium hydroxide; water / methanol / 5 h / Inert atmosphere; Reflux 2: boron tribromide / dichloromethane / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: copper diacetate; potassium hydroxide; 1,10-Phenanthroline; oxygen / water; dimethyl sulfoxide / 1 h / 110 °C / Microwave irradiation 2: 1,10-Phenanthroline; copper(l) iodide / 0.17 h / 180 °C / Microwave irradiation 3: aluminum (III) chloride / 1,2-dichloro-ethane / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1,10-Phenanthroline; copper(l) iodide / 0.17 h / 180 °C / Microwave irradiation 2: aluminum (III) chloride / 1,2-dichloro-ethane / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: triethylamine; acetic anhydride / 6 h / 110 °C 2: copper diacetate; potassium hydroxide; 1,10-Phenanthroline; oxygen / water; dimethyl sulfoxide / 1 h / 110 °C / Microwave irradiation 3: 1,10-Phenanthroline; copper(l) iodide / 0.17 h / 180 °C / Microwave irradiation 4: aluminum (III) chloride / 1,2-dichloro-ethane / 80 °C | ||
Multi-step reaction with 4 steps 1: acetic anhydride; triethylamine / 7 h / 110 °C 2: copper diacetate; 1,10-Phenanthroline; potassium hydroxide / dimethyl sulfoxide; water / 1 h / 120 °C / Microwave irradiation 3: copper(II) oxide; 8-quinolinol; 1,10-Phenanthroline / 0.13 h / 200 °C / Microwave irradiation 4: aluminum (III) chloride / chloroform / 9 h / 65 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: triethylamine; acetic anhydride / 6 h / 110 °C 2: copper diacetate; potassium hydroxide; 1,10-Phenanthroline; oxygen / water; dimethyl sulfoxide / 1 h / 110 °C / Microwave irradiation 3: 1,10-Phenanthroline; copper(l) iodide / 0.17 h / 180 °C / Microwave irradiation 4: aluminum (III) chloride / 1,2-dichloro-ethane / 80 °C | ||
Multi-step reaction with 4 steps 1: acetic anhydride; triethylamine / 7 h / 110 °C 2: copper diacetate; 1,10-Phenanthroline; potassium hydroxide / dimethyl sulfoxide; water / 1 h / 120 °C / Microwave irradiation 3: copper(II) oxide; 8-quinolinol; 1,10-Phenanthroline / 0.13 h / 200 °C / Microwave irradiation 4: aluminum (III) chloride / chloroform / 9 h / 65 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: -78 - 20 °C 1.3: 20 °C / pH 5 2.1: potassium carbonate; palladium diacetate; tricyclohexylphosphine / water; 1,2-dimethoxyethane / 2 h / 80 °C / Inert atmosphere 3.1: 1H-imidazole / tetrahydrofuran / 2 h / 20 °C 4.1: n-butyllithium; diphenylphosphane / tetrahydrofuran; hexane / 36 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate; palladium diacetate; tricyclohexylphosphine / water; 1,2-dimethoxyethane / 2 h / 80 °C / Inert atmosphere 2: 1H-imidazole / tetrahydrofuran / 2 h / 20 °C 3: n-butyllithium; diphenylphosphane / tetrahydrofuran; hexane / 36 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With n-butyllithium; diphenylphosphane In tetrahydrofuran; hexane for 36h; Inert atmosphere; Reflux; | 5-(6-Hydroxybenzofuran-2-yl)-2-(3-methyl-2-butenyl)-1,3-benzenediol (1) General procedure: ). n-Butyllithium (2.4 M inhexane, 2.25 mL, 5.4 mmol) was added over 1 h to a stirred solution ofdiphenylphosphine (940 μL, 5.4 mmol) in dry THF (8 mL) at 0°C under nitrogen. 34 (404 mg, 0.9 mmol) in dry THF (4 mL) wasadded and the solution was allowed to warm to room temperature. The mixture washeated under reflux for 36 h and was then poured into 4 M aqueous sodiumhydroxide (8 mL), acidified with 4 M aqueous HCl and extracted into ethylacetate. The organic extract was dried with anhydrous sodium sulfate and thesolvent removed in vacuo. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: 1H-imidazole / tetrahydrofuran / 4 h / 0 - 20 °C 2.1: sodium tetrahydroborate / methanol / 4 h / 20 °C 3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 3.2: -78 - 20 °C 3.3: 20 °C / pH 5 4.1: potassium carbonate; palladium diacetate; tricyclohexylphosphine / water; 1,2-dimethoxyethane / 2 h / 80 °C / Inert atmosphere 5.1: 1H-imidazole / tetrahydrofuran / 2 h / 20 °C 6.1: n-butyllithium; diphenylphosphane / tetrahydrofuran; hexane / 36 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: copper diacetate; 1,10-Phenanthroline; potassium hydroxide / dimethyl sulfoxide; water / 1 h / 120 °C / Microwave irradiation 2: copper(II) oxide; 8-quinolinol; 1,10-Phenanthroline / 0.13 h / 200 °C / Microwave irradiation 3: aluminum (III) chloride / chloroform / 9 h / 65 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 2: boron tribromide / dichloromethane | ||
Multi-step reaction with 2 steps 1: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 2: boron tribromide / dichloromethane | ||
Multi-step reaction with 3 steps 1: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 2: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C 3: boron tribromide / dichloromethane / 24 h / -78 - 20 °C |
Multi-step reaction with 3 steps 1: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 2: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C 3: boron tribromide / dichloromethane / 24 h / -78 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: triphenylphosphine / dichloromethane / 0.75 h / 0 °C 1.2: 0.08 h / 0 °C 1.3: 14.5 h / 0 - 20 °C 2.1: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 3.1: boron tribromide / dichloromethane | ||
Multi-step reaction with 4 steps 1.1: triphenylphosphine / dichloromethane / 0.75 h / 0 °C 1.2: 0.08 h / 0 °C 1.3: 14.5 h / 0 - 20 °C 2.1: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 3.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C 4.1: boron tribromide / dichloromethane / 24 h / -78 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: triphenylphosphine / dichloromethane / 14.5 h / 0 - 20 °C 2: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 3: boron tribromide / dichloromethane | ||
Multi-step reaction with 4 steps 1: triphenylphosphine / dichloromethane / 14.5 h / 0 - 20 °C 2: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 3: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C 4: boron tribromide / dichloromethane / 24 h / -78 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With boron tribromide In dichloromethane at -78 - 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 2: boron tribromide / dichloromethane | ||
Multi-step reaction with 3 steps 1: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 2: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C 3: boron tribromide / dichloromethane / 24 h / -78 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 2: boron tribromide / dichloromethane | ||
Multi-step reaction with 3 steps 1: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 7 h / 90 °C / Schlenk technique; Inert atmosphere 2: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C 3: boron tribromide / dichloromethane / 24 h / -78 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In water; N,N-dimethyl-formamide for 1h; Inert atmosphere; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 2 h / 100 °C / Inert atmosphere 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium phosphate / water; N,N-dimethyl-formamide / 1 h / Inert atmosphere; Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: caesium carbonate; copper(l) iodide / acetonitrile / 3 h / 80 °C / Inert atmosphere 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium phosphate / water; N,N-dimethyl-formamide / 1 h / Inert atmosphere; Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: indium(III) triflate / tetrahydrofuran / 12 h / 100 °C / Inert atmosphere; Schlenk technique 2: boron tribromide / dichloromethane / 8 h / -78 - 20 °C / Inert atmosphere; Schlenk technique |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: potassium carbonate; iodine / tetrahydrofuran / 2 h / 20 °C / Schlenk technique; Inert atmosphere 2.1: boron tribromide / dichloromethane / 24 h / -78 - 25 °C / Schlenk technique; Inert atmosphere 2.2: Schlenk technique; Inert atmosphere; Cooling with ice |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: potassium carbonate / acetone; dichloromethane / 7 h / 55 °C / Schlenk technique; Inert atmosphere; Sealed tube 2.1: potassium carbonate; iodine / tetrahydrofuran / 2 h / 20 °C / Schlenk technique; Inert atmosphere 3.1: boron tribromide / dichloromethane / 24 h / -78 - 25 °C / Schlenk technique; Inert atmosphere 3.2: Schlenk technique; Inert atmosphere; Cooling with ice |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: sodium nitrite; hydrogenchloride / ethanol; water / 2.17 h / 0 °C / Schlenk technique; Inert atmosphere 2.1: potassium carbonate / acetone; dichloromethane / 7 h / 55 °C / Schlenk technique; Inert atmosphere; Sealed tube 3.1: potassium carbonate; iodine / tetrahydrofuran / 2 h / 20 °C / Schlenk technique; Inert atmosphere 4.1: boron tribromide / dichloromethane / 24 h / -78 - 25 °C / Schlenk technique; Inert atmosphere 4.2: Schlenk technique; Inert atmosphere; Cooling with ice |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / N,N-dimethyl-formamide / 0.08 h / Inert atmosphere 1.2: 15 h / Inert atmosphere 2.1: boron tribromide / dichloromethane / 3 h / -78 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / N,N-dimethyl-formamide / 0.08 h / Inert atmosphere 1.2: 15 h / Inert atmosphere 2.1: boron tribromide / dichloromethane / 3 h / -78 - 20 °C / Inert atmosphere |