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CAS No. : | 524-12-9 | MDL No. : | MFCD07778564 |
Formula : | C16H10O7 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XQDCKJKKMFWXGB-UHFFFAOYSA-N |
M.W : | 314.25 | Pubchem ID : | 5281813 |
Synonyms : |
IKK Inhibitor II
|
Num. heavy atoms : | 23 |
Num. arom. heavy atoms : | 17 |
Fraction Csp3 : | 0.06 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 7.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 82.32 |
TPSA : | 113.27 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -6.53 cm/s |
Log Po/w (iLOGP) : | 1.92 |
Log Po/w (XLOGP3) : | 2.38 |
Log Po/w (WLOGP) : | 2.82 |
Log Po/w (MLOGP) : | 0.93 |
Log Po/w (SILICOS-IT) : | 2.42 |
Consensus Log Po/w : | 2.09 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.77 |
Solubility : | 0.0535 mg/ml ; 0.00017 mol/l |
Class : | Soluble |
Log S (Ali) : | -4.4 |
Solubility : | 0.0125 mg/ml ; 0.0000398 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -4.56 |
Solubility : | 0.00862 mg/ml ; 0.0000274 mol/l |
Class : | Moderately soluble |
PAINS : | 1.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 3.29 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280 | UN#: | N/A |
Hazard Statements: | H302-H317 | 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 |
---|---|---|
29% | With potassium carbonate In N,N-dimethyl-formamide for 0.833333h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25% | With sodium acetate; potassium hexacyanoferrate(III) In water; acetone for 2h; Ambient temperature; | |
With ascorbic acid 1.) tyrosinase, pH=6.8, r.t., 1 h; Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With hydrogen In 1,4-dioxane 2nd step of purification of 9 (wedelolactone); | |
81% | With boron trichloride In dichloromethane at 0℃; Inert atmosphere; | Preparation of WEL 5 To a solution of 17 (0.58 g, 1.0 mmol) in DCM (15 mL) was added BCl3(3 mL, 1 M) slowly at 0 C under Ar atmosphere. After the reaction was finished, the mixture wasconcentrated and then purified by column chromatography (MeOH:DCM = 1:20) to give the product 5.Gray solid; 254 mg, 81% yield; m.p. >300 C; Rf: 0.48 (MeOH:DCM = 1:10); IR (cm1): 3397, 2955, 2923,2853, 1710, 1670, 1612, 1447, 1324, 1284, 1206, 1151, 1070, 1047; 1H-NMR (DMSO-d6, 300 MHz): 3.82 (s,3H), 6.45 (d, J = 1.8 Hz, 1H), 6.62 (d, J = 1.9 Hz, 1H), 7.16 (s, 1H), 7.24 (s, 1H); 13C-NMR (DMSO-d6,75 MHz): 55.7, 93.2, 96.7, 98.1, 98.8, 101.7, 104.5, 113.7, 144.3, 145.4, 148.8, 154.8, 155.2, 157.7, 158.9,162.2; HR-MS (ESI) calculated for C16H11O7 [M + H] 315.0505, found 315.0504. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Tri-O-methylwedelolacton i. Acetanhydrid + HI (115-120grad); | ||
Tri-O-methylwedelolacton /Acetanhydrid, HI, 115-120grad; | ||
Brenzcatechin, 4,5-Dihydroxy-7-methoxy-cumarin, Kaliumhexacyanoferrat (III), Natriumacetat, aq.Aceton, (blaue Lsg. wird rotbraun); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen iodide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In tetrahydrofuran at 25℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With sulfuric acid; acetic acid In water at 50℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: m-chloroperbenzoic acid / CH2Cl2; H2O / 15 h / 20 °C 1.2: 90 percent / K2CO3 / methanol / 0.5 h / 25 °C 2.1: 99 percent / Et3N / tetrahydrofuran / 2 h / 25 °C 3.1: 94 percent / N-iodosuccinimide; trifluoroacetic acid / acetonitrile / 12 h / 40 °C 4.1: 90 percent / CuI; Et3N / PdCl2(PPh3)2 / acetonitrile / 12 h / 25 °C 5.1: 98 percent / hydrazine monohydrate / tetrahydrofuran / 2 h / 25 °C 6.1: 87 percent / thiourea; Cs2CO3; CBr4 / PdI2 / tetrahydrofuran / 2 h / 50 °C 7.1: 93 percent / H2 / Pd/C / ethyl acetate / 24 h / 25 °C 8.1: 93 percent / AcOH; H2SO4 / H2O / 1 h / 50 °C | ||
Multi-step reaction with 8 steps 1.1: 3-chloro-benzenecarboperoxoic acid / water; dichloromethane / 15 h / 20 °C 1.2: 0.5 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 2.2: 20 °C 3.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 4.5 h / 0 - 20 °C 4.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 80 °C / Inert atmosphere 5.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; tetrahydrofuran / 12 h / 90 °C / Inert atmosphere 6.1: potassium carbonate / N,N-dimethyl-formamide 7.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 24 h / Reflux 8.1: boron trichloride / dichloromethane / 0 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: 94 percent / N-iodosuccinimide; trifluoroacetic acid / acetonitrile / 12 h / 40 °C 2: 90 percent / CuI; Et3N / PdCl2(PPh3)2 / acetonitrile / 12 h / 25 °C 3: 98 percent / hydrazine monohydrate / tetrahydrofuran / 2 h / 25 °C 4: 87 percent / thiourea; Cs2CO3; CBr4 / PdI2 / tetrahydrofuran / 2 h / 50 °C 5: 93 percent / H2 / Pd/C / ethyl acetate / 24 h / 25 °C 6: 93 percent / AcOH; H2SO4 / H2O / 1 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: t-BuOK / tetrahydrofuran / 0.5 h / 0 °C 1.2: 75 percent / t-BuOK / tetrahydrofuran / 0 - 25 °C 2.1: 90 percent / CuI; Et3N / PdCl2(PPh3)2 / acetonitrile / 12 h / 25 °C 3.1: 98 percent / hydrazine monohydrate / tetrahydrofuran / 2 h / 25 °C 4.1: 87 percent / thiourea; Cs2CO3; CBr4 / PdI2 / tetrahydrofuran / 2 h / 50 °C 5.1: 93 percent / H2 / Pd/C / ethyl acetate / 24 h / 25 °C 6.1: 93 percent / AcOH; H2SO4 / H2O / 1 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 9 steps 1.1: 94 percent / K2CO3; n-Bu4NI / acetone / 24 h / Heating 2.1: m-chloroperbenzoic acid / CH2Cl2; H2O / 15 h / 20 °C 2.2: 90 percent / K2CO3 / methanol / 0.5 h / 25 °C 3.1: 99 percent / Et3N / tetrahydrofuran / 2 h / 25 °C 4.1: 94 percent / N-iodosuccinimide; trifluoroacetic acid / acetonitrile / 12 h / 40 °C 5.1: 90 percent / CuI; Et3N / PdCl2(PPh3)2 / acetonitrile / 12 h / 25 °C 6.1: 98 percent / hydrazine monohydrate / tetrahydrofuran / 2 h / 25 °C 7.1: 87 percent / thiourea; Cs2CO3; CBr4 / PdI2 / tetrahydrofuran / 2 h / 50 °C 8.1: 93 percent / H2 / Pd/C / ethyl acetate / 24 h / 25 °C 9.1: 93 percent / AcOH; H2SO4 / H2O / 1 h / 50 °C | ||
Multi-step reaction with 9 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: 3-chloro-benzenecarboperoxoic acid / water; dichloromethane / 15 h / 20 °C 2.2: 0.5 h / 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 3.2: 20 °C 4.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 4.5 h / 0 - 20 °C 5.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 80 °C / Inert atmosphere 6.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; tetrahydrofuran / 12 h / 90 °C / Inert atmosphere 7.1: potassium carbonate / N,N-dimethyl-formamide 8.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 24 h / Reflux 9.1: boron trichloride / dichloromethane / 0 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 90 percent / CuI; Et3N / PdCl2(PPh3)2 / acetonitrile / 12 h / 25 °C 2: 98 percent / hydrazine monohydrate / tetrahydrofuran / 2 h / 25 °C 3: 87 percent / thiourea; Cs2CO3; CBr4 / PdI2 / tetrahydrofuran / 2 h / 50 °C 4: 93 percent / H2 / Pd/C / ethyl acetate / 24 h / 25 °C 5: 93 percent / AcOH; H2SO4 / H2O / 1 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 90 percent / CuI; Et3N / PdCl2(PPh3)2 / acetonitrile / 12 h / 25 °C 2: 98 percent / hydrazine monohydrate / tetrahydrofuran / 2 h / 25 °C 3: 87 percent / thiourea; Cs2CO3; CBr4 / PdI2 / tetrahydrofuran / 2 h / 50 °C 4: 93 percent / H2 / Pd/C / ethyl acetate / 24 h / 25 °C 5: 93 percent / AcOH; H2SO4 / H2O / 1 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 87 percent / thiourea; Cs2CO3; CBr4 / PdI2 / tetrahydrofuran / 2 h / 50 °C 2: 93 percent / H2 / Pd/C / ethyl acetate / 24 h / 25 °C 3: 93 percent / AcOH; H2SO4 / H2O / 1 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 98 percent / hydrazine monohydrate / tetrahydrofuran / 2 h / 25 °C 2: 87 percent / thiourea; Cs2CO3; CBr4 / PdI2 / tetrahydrofuran / 2 h / 50 °C 3: 93 percent / H2 / Pd/C / ethyl acetate / 24 h / 25 °C 4: 93 percent / AcOH; H2SO4 / H2O / 1 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 93 percent / H2 / Pd/C / ethyl acetate / 24 h / 25 °C 2: 93 percent / AcOH; H2SO4 / H2O / 1 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: hydrogenchloride / diethyl ether / 2 h 2: hydrogenchloride / 1 h / Heating 3: sodium carbonate / water / 1 h / 80 °C 4: ascorbic acid / 1.) tyrosinase, pH=6.8, r.t., 1 h | ||
Multi-step reaction with 8 steps 1.1: zinc(II) chloride / 2 h / 100 °C 2.1: potassium carbonate / acetone / 1 h / 90 °C 2.2: 1.5 h / 90 °C 3.1: bromine / dichloromethane / 8 h / 0 - 10 °C 3.2: 1 h / 20 °C 4.1: potassium carbonate / acetone / 56 °C 5.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; tetrahydrofuran / 12 h / 90 °C / Inert atmosphere 6.1: potassium carbonate / N,N-dimethyl-formamide 7.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 24 h / Reflux 8.1: boron trichloride / dichloromethane / 0 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: hydrogenchloride / 1 h / Heating 2: sodium carbonate / water / 1 h / 80 °C 3: ascorbic acid / 1.) tyrosinase, pH=6.8, r.t., 1 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium carbonate / water / 1 h / 80 °C 2: ascorbic acid / 1.) tyrosinase, pH=6.8, r.t., 1 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With boron trichloride In dichloromethane at 0℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 24 h / Reflux 2: boron trichloride / dichloromethane / 0 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; tetrahydrofuran / 12 h / 90 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide 3: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 24 h / Reflux 4: boron trichloride / dichloromethane / 0 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: N-Bromosuccinimide / N,N-dimethyl-formamide / 4.5 h / 0 - 20 °C 2: triethylamine; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 80 °C / Inert atmosphere 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; tetrahydrofuran / 12 h / 90 °C / Inert atmosphere 4: potassium carbonate / N,N-dimethyl-formamide 5: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 24 h / Reflux 6: boron trichloride / dichloromethane / 0 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 80 °C / Inert atmosphere 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; tetrahydrofuran / 12 h / 90 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide 4: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 24 h / Reflux 5: boron trichloride / dichloromethane / 0 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: bromine / dichloromethane / 8 h / 0 - 10 °C 1.2: 1 h / 20 °C 2.1: potassium carbonate / acetone / 56 °C 3.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; tetrahydrofuran / 12 h / 90 °C / Inert atmosphere 4.1: potassium carbonate / N,N-dimethyl-formamide 5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 24 h / Reflux 6.1: boron trichloride / dichloromethane / 0 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: potassium carbonate / acetone / 56 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; tetrahydrofuran / 12 h / 90 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide 4: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 24 h / Reflux 5: boron trichloride / dichloromethane / 0 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; tetrahydrofuran / 12 h / 90 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide 3: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 24 h / Reflux 4: boron trichloride / dichloromethane / 0 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide 2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 24 h / Reflux 3: boron trichloride / dichloromethane / 0 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / acetone / 0 - 25 °C / Schlenk technique 2: sodium / Heating; Schlenk technique 3: catechol oxidase from Ipomoea batatas (sweet potato) / aq. phosphate buffer / 24 h / 25 °C / pH 7.4 / Schlenk technique; Enzymatic reaction |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55 % | With potassium carbonate In acetone at 0 - 25℃; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52 % | With potassium carbonate In acetone at 0 - 25℃; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71 % | With hydrogenchloride In ethanol at 78℃; | Wedelolactone (1) Compound 2 (40.00 mg, 0.09 mmol) was dissolved in saturated ethanol hydrochloride (1 mL), and the reaction solution was stirred at 78 °C for 6 h. After completion of the reaction, the reaction mixture was quenched with saturated NaHCO3 and extracted with ethyl acetate (5 mL 3). The combined organic layers were washed with brine (15 mL), dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, MeOH/DCM = 1:10, v/v) to obtain compound 1 (20 mg, 71%) as a white solid. mp 299-301 °C. IR (νmax, cm-1) ν 3360, 3139, 3037, 2995, 2942, 1786, 1661, 1510, 1458, 1401, 1361, 1248, 1164, 1044; 1HNMR (400 MHz, DMSO-d6) δ 10.97 (s,1H, -OH), 9.43 (s, 1H, -OH),9.38 (s, 1H, -OH), 7.24 (s, 1H, -ArH), 7.17(s, 1H, -ArH), 6.64 (d, J = 2.3 Hz,1H, -ArH), 6.47 (d, J = 2.3 Hz, 1H, -ArH), 3.83 (s, 3H, -CH3); 13C NMR (101 MHz, DMSO) δ 162.7, 159.4 158.2, 155.7, 155.3, 149.3, 145.9, 144.8, 114.2, 105.0, 102.1, 99.3, 98.6, 97.1, 93.7, 56.2. HRMS: m/z calcd for C16H11O7 [M+H]+ 315.0494; found: 315.0497. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: tetrafluoroboric acid diethyl ether / toluene; tetrahydrofuran / 12 h / -78 - 20 °C 1.2: 4 h / 20 °C 2.1: 1H-imidazole / N,N-dimethyl-formamide / 3 h / 20 °C 3.1: N-iodo-succinimide; acetic acid / dichloromethane / 12 h / 60 °C 4.1: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / 1,4-dioxane; water / 24 h / 80 °C 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C 6.1: hydrogenchloride / ethanol / 6 h / 78 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: aluminum (III) chloride / toluene / 12 h / 0 - 20 °C 2.1: tetrafluoroboric acid diethyl ether / toluene; tetrahydrofuran / 12 h / -78 - 20 °C 2.2: 4 h / 20 °C 3.1: 1H-imidazole / N,N-dimethyl-formamide / 3 h / 20 °C 4.1: N-iodo-succinimide; acetic acid / dichloromethane / 12 h / 60 °C 5.1: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / 1,4-dioxane; water / 24 h / 80 °C 6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C 7.1: hydrogenchloride / ethanol / 6 h / 78 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one / dichloromethane; 1,4-dioxane / 16 h / 0 °C 2.1: acetyl chloride; zinc dibromide / 2 h / 0 - 20 °C / Inert atmosphere 2.2: 3 h / 20 °C / Inert atmosphere 3.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 1,4-dioxane / 12 h / 85 °C / Inert atmosphere 4.1: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / 1,4-dioxane; water / 24 h / 80 °C 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C 6.1: hydrogenchloride / ethanol / 6 h / 78 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: acetyl chloride; zinc dibromide / 2 h / 0 - 20 °C / Inert atmosphere 1.2: 3 h / 20 °C / Inert atmosphere 2.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 1,4-dioxane / 12 h / 85 °C / Inert atmosphere 3.1: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / 1,4-dioxane; water / 24 h / 80 °C 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C 5.1: hydrogenchloride / ethanol / 6 h / 78 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 1,4-dioxane / 12 h / 85 °C / Inert atmosphere 2: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / 1,4-dioxane; water / 24 h / 80 °C 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C 4: hydrogenchloride / ethanol / 6 h / 78 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / 1,4-dioxane; water / 24 h / 80 °C 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C 3: hydrogenchloride / ethanol / 6 h / 78 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 1H-imidazole / N,N-dimethyl-formamide / 3 h / 20 °C 2: N-iodo-succinimide; acetic acid / dichloromethane / 12 h / 60 °C 3: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / 1,4-dioxane; water / 24 h / 80 °C 4: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C 5: hydrogenchloride / ethanol / 6 h / 78 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N-iodo-succinimide; acetic acid / dichloromethane / 12 h / 60 °C 2: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / 1,4-dioxane; water / 24 h / 80 °C 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C 4: hydrogenchloride / ethanol / 6 h / 78 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / 1,4-dioxane; water / 24 h / 80 °C 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C 3: hydrogenchloride / ethanol / 6 h / 78 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C 2: hydrogenchloride / ethanol / 6 h / 78 °C |