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CAS No. : | 14588-08-0 | MDL No. : | MFCD00010013 |
Formula : | C40H36O4P2Pd | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 749.08 | Pubchem ID : | - |
Synonyms : |
|
Num. heavy atoms : | 47 |
Num. arom. heavy atoms : | 36 |
Fraction Csp3 : | 0.05 |
Num. rotatable bonds : | 12 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 194.21 |
TPSA : | 79.78 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -4.18 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 9.42 |
Log Po/w (WLOGP) : | 6.92 |
Log Po/w (MLOGP) : | 6.64 |
Log Po/w (SILICOS-IT) : | 6.77 |
Consensus Log Po/w : | 5.95 |
Lipinski : | 2.0 |
Ghose : | None |
Veber : | 1.0 |
Egan : | 1.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.17 |
Log S (ESOL) : | -10.19 |
Solubility : | 0.000000048 mg/ml ; 0.0000000001 mol/l |
Class : | Insoluble |
Log S (Ali) : | -11.0 |
Solubility : | 0.0000000075 mg/ml ; 0.0 mol/l |
Class : | Insoluble |
Log S (SILICOS-IT) : | -15.22 |
Solubility : | 0.0 mg/ml ; 6.01e-16 mol/l |
Class : | Insoluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 3.0 |
Synthetic accessibility : | 6.54 |
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: |
* 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 |
---|---|---|
In dichloromethane-d2 | 54 A solution of Pd(OAc)2(P(Ph)3)2 (25 mg, 33.4 μmol) in CD2Cl2 (0.5 mL) was stirred as a solution of DANFABA (27 mg, 33.4 μmol) in CD2Cl2 (0.5 mL) was added drop-wise via pipet. The resulting deep red solution was sealed in an NMR tube and subjected to NMR analysis. Result: The 1H and 31P NMR analysis showed the formation of at least 6 products including an orthometalated product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane-d2 | 52 A solution of Pd(OAc)2(P(Ph)3)2 (25 mg, 33.4 μmol) in CD2Cl2 (0.5 mL) was stirred as a solution of tritylFABA (31 mg, 33.4 μmol) in CD2Cl2 (0.5 mL) was added drop-wise via pipet. The resulting deep red/black solution was sealed in an NMR tube and subjected to NMR analysis. Result: The 1H and 31P NMR analysis showed the formation of at least 6 products including an orthometalated product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A solution of Pd(OAc)2(P(Ph)3)2 (25 mg, 33.4 mumol) in CD3CN (0.5 mL) was stirred as a solution of Li(OEt2)2.5FABA (29 mg, 33.4 mumol) in CD3CN (0.5 mL) was added drop-wise via pipet. The resulting yellow solution was sealed in an NMR tube and subjected to NMR analysis. Result: Both 1H and 31P NMR analysis showed the formation of a single product. 31P{1H} NMR (CD3CN, delta): 32.8 (s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane-d2 | 53 A solution of Pd(OAc)2(PPh3)2 (25 mg, 33.4 μmol) in CD2Cl2 (0.5 mL) was stirred as a solution of Li(OEt2)2.5FABA (29 mg, 33.4 μmol) in CD2Cl2 (0.5 mL) was added drop-wise via pipet. The resulting deep red solution was sealed in an NMR tube and subjected to NMR analysis. Result: The 1H and 31P NMR analysis showed the formation of at least 6 products including an orthometalated product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In not given N2-atmosphere, 12 h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N,N-dimethyl-formamide; at 100.0℃; for 0.166667 - 0.25h;Product distribution / selectivity; | A mixture of PPh3 (4.28 g, 16.3 mmol) and Pd(OAc)2 (1.83 g, 8.16 mmol) were stirred in DMF (90 mL). The mixture was degassed with nitrogen then heated at about 100° C. for about 10 min until it was a dark red solution. The reaction was removed from heating then 2-(2,4-difluorophenyl)-8-methylimidazo[1,2-a]pyrazine (10.0 g, 40.8 mmol) and CsOAc (15.7 g, 81.8 mmol) were added. The reaction was returned to heating at about 100° C. and a solution of 4-iodo-2-(methylthio)pyrimidine (20.56 g, 81.6 mmol) in DMF (40 mL) was added via addition funnel over about 4 h. The reaction was heated at about 100° C. for about 16 hours after the addition ended then cooled to ambient temperature and concentrated under reduced pressure. The resulting solid was dissolved in DCM (500 mL) and washed with 1 N HCl (5.x.200 mL) then washed with 0.5 N NaOH (200 mL) and filtered through Celite.(R). to break the resulting emulsion. The layers were separated and the organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. The resulting residue was filtered through a silica gel plug using EtOAc then concentrated under reduced pressure and dissolved in DCM (200 mL). The DCM solution was purified by silica gel chromatography (330 g column) using a gradient of DCM:ACN (1:0 for 4 min, cut to 4:1 and held for 40 min, ramped to 1:1 over 20 min and held until product finished eluting). All product-containing fractions (including those with triphenylphosphine oxide) were combined and concentrated under reduced pressure until heavy precipitate present in a dark liquid. Then IPA was added and further concentrated under reduced pressure to remove DCM. The resulting suspension was filtered, washing with IPA followed by petroleum ether (b.p. 30-60° C.) and dried in vacuum oven at about 70° C. to give the title compound (5.7 g, 38percent): LC/MS (Table 1, Method a) Rt=3.39 min; MS m/z: 370.3 (M+H)+; A mixture of PPh3 (4.28 g, 16.3 mmol) and Pd(OAc)2 (1.83 g, 8.16 mmol) were stirred in DMF (90 mL). The mixture was degassed with nitrogen then heated at about 100° C. for about 10 min until it was a dark red solution. The reaction was removed from heating then 2-(2,4-difluorophenyl)-8-methylimidazo[1,2-a]pyrazine (10.0 g, 40.8 mmol) and CsOAc (15.7 g, 81.8 mmol) were added. The reaction was returned to heating at about 100° C. and a solution of 4-iodo-2-(methylthio)pyrimidine (20.56 g, 81.6 mmol) in DMF (40 mL) was added via addition funnel over about 4 h. The reaction was heated at about 100° C. for about 16 hours after the addition ended then cooled to ambient temperature and concentrated under reduced pressure. The resulting solid was dissolved in DCM (500 mL) and washed with 1 N HCl (5.x.200 mL) then washed with 0.5 N NaOH (200 mL) and filtered through Celite.(R). to break the resulting emulsion. The layers were separated and the organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. The resulting residue was filtered through a silica gel plug using EtOAc then concentrated under reduced pressure and dissolved in DCM (200 mL). The DCM solution was purified by silica gel chromatography (330 g column) using a gradient of DCM:ACN (1:0 for 4 min, cut to 4:1 and held for 40 min, ramped to 1:1 over 20 min and held until product finished eluting). All product-containing fractions (including those with triphenylphosphine oxide) were combined and concentrated under reduced pressure until heavy precipitate present in a dark liquid. Then IPA was added and further concentrated under reduced pressure to remove DCM. The resulting suspension was filtered, washing with IPA followed by petroleum ether (b.p. 30-60° C.) and dried in vacuum oven at about 70° C. to give the title compound (5.7 g, 38percent): LC/MS (Table 1, Method a) Rt=3.39 min; MS m/z: 370.3 (M+H)+; A mixture of PPh3 (6.12 g, 23.3 mmol) and Pd(OAc)2 (2.62 g, 11.7 mmol) were stirred in DMF (136 mL). The mixture was degassed with nitrogen then heated at about 100° C. for about 15 min until it was a dark red solution. The reaction was removed from heating then 2-(2,4-difluorophenyl)-8-ethylimidazo[1,2-a]pyrazine (15.1 g, 58.3 mmol) and CsOAc (15.7 g, 81.8 mmol) were added. The reaction was returned to heating and a solution of 4-iodo-2-(methylthio)pyrimidine (29.4 g, 117 mmol) in DMF (60 mL) was added via syringe pump over about 8 hours. The reaction was heated for about 15 hours after the addition ended then concentrated under reduced pressure. The resulting crude material was dissolved in DCM (600 mL) and washed with 1 N HCl (5.x.300 mL) followed by 0.5 N NaOH (300 mL) then filtered the resulting emulsion through Celite.(R).. The layers of the filtrate were separated and the organic layer was washed with brine (2.x.300 mL), dried over MgSO4, filtered, and concentrated under reduced pressure. The crude material was purified by silica gel chromatography (330 g column) using a gradient of DCM:ACN (1:0 for 4 min, ramped to 4:1 over 1 min, held for 35... |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In ethanol; for 0.666667h; | To a 0.1mmol of trans-[Pd(OAc)2(PPh3)2] in 20mL EtOH a slight excess of H2SO4 was added dropwise. After ca. 10min a yellow solid precipitated. The suspension was stirred for 30 minutes more. After adding 20mL of petrol ether, the solid was collected on a filter, washed with H2O, EtOH, petroleum ether and dried under vacuum. Yield 80percent. Elem. anal. calcd for C36H30O4SP2Pd: C, 58.69, H, 4.08; found: C, 59.05; H, 4.06. NMR: 1H 7.66?6.94 (m, 30H, Ph), 31P{1H} 35.0 (s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrazine hydrate In tetrahydrofuran at 20℃; for 0.5h; | Synthesis of [(Ph3P)2Pd{C6H3-2-(N=N-N(Me)Ph)-5-COOEt}Br] (5): Bis(triphenylphosphane)palladium diacetate (315mg, 0.42mmol) was suspended in 10mL of anhydrous tetrahydrofuran. After the suspension was stirred for 10min, hydrazine monohydrate (11μL, 11.1mg, 0.22mmol) was added. The final clear greenish brown solution was stirred for 30minat r.t. Then 1-(2-bromo-4-ethoxycarbonylphenyl)-3-methyl-3-phenyltriazene (2) (152.5mg, 0.42mmol) was dissolved in anhydrous tetrahydrofuran (5mL) and added via a cannula to the thus prepared palladium(0) solution. The reaction mixture was heated to 60°C for 4h. After cooling to r.t. all volatiles were removed in vacuo. The residue was washed three times with n-pentane (3x5 mL). Then the crude product was washed twice with diethyl ether (2x3 mL). Drying in vacuo gave a grey-brown powder. Yield: 225mg of 5 (75%). Rerystallization was achieved in toluene/n-hexane yielding orange rhombohedral crystals. (0030) Physical data of 5: Dec. without melting. 1H NMR (600MHz, [D8]THF, 298K): δ=1.21 (t, J=7.1Hz, 3H, COOEt CH3), 3.73 (s, 3H, NCH3), 4.08 (q, J=7.1Hz, 2H, COOEt CH2), 6.43 (d, J=8.2Hz, 1H, subArH 6-CH), 7.01 (d, J=8.2Hz, 1H, subArH 3-CH), 7.04 (m, 1H, ArH 4-CH), 7.17 (t, J=7.5Hz, 12H, PPh3 2,2′-CH), 7.25 (t, J=7.3Hz, 6H, PPh3 4-CH), 7.30 (m, 5H, ArH 2,2′-CH, 3,3′-CH sub ArH 5-CH), 7.59 (m, 12H, PPh3 3,3′-CH). 13C{1H} NMR (150MHz, [D8]THF, 297K): δ=14.7 (COOEt CH3), 32.9 (NCH3), 60.0 (COOEt CH2), 117.2 (subAr 6-CH), 117.3 (Ar 2,2′-CH), 123.6 (Ar, 4-CH), 125.1 (subAr 3-CH), 128.0 (subAr CPd), 128.2 (t, 2JPC=5.1Hz, PPh3 2,2′-CH), 129.5 (PPh3 4-CH), 130.2 (Ar 3,3′-CH), 132.7 (t, 1JPC=22.9Hz, PPh3 1-C), 135.6 (t, 3JPC=6.3Hz, PPh3 3,3′-CH), 139.3 (t, 5JPC=4.6Hz, subAr 5-CH), 146.0 (Ar 1-CN), 156.9 (t 4JPC=2.5Hz, subAr 4-C), 158.4 (t, 3JPC=3.7Hz, subAr 1-CN), 166.1 (COOEt). 31P{1H} NMR (243MHz, [D8]THF, 297K): δ=23.56. HR-MS (ESI, acetonitrile), [(M-PPh3-Br)]+: calculated for C34H32N3O2PPd: 650.1196Da, found: 650.1219Da, Δm/z=5.5ppm. IR (ATR, cm-1): 3052, 1707, 1597, 1503, 1479, 1433, 1363, 1333, 1271, 1228, 1204, 1101, 1026, 994, 825, 742, 726, 687, 608, 520, 509, 492, 453, 438, 414. Elemental anal. (C52H46BrN3O2P2Pd): calcd.: C 62.88, H 4.67, Br 8.05, N 4.23; found: C 61.88, H 4.60, Br 7.43, N 3.75. TGA-DSC (m0=6.0109mg, 25°C-600°C, 5K/min): three step degradation, 1. step: 10.31% (216.9°C, proceeds exothermic with 25.9J/g), 2. step: 31.34% (309.3°C), 3. step: 31.8% (356.5°C), residue: 25.04%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With triethylamine In dichloromethane for 3h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With triethylamine In dichloromethane for 3h; Reflux; |