Alternatived Products of [ 909389-74-8 ]
Product Details of [ 909389-74-8 ]
CAS No. : 909389-74-8
MDL No. : MFCD08445663
Formula :
C8 H6 Br2 O2
Boiling Point : -
Linear Structure Formula : -
InChI Key : QPXGHGNAEBFULS-UHFFFAOYSA-N
M.W : 293.94 Pubchem ID : 26967130
Synonyms :
Calculated chemistry of [ 909389-74-8 ]
Physicochemical Properties
Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 53.34
TPSA : 26.3 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) : -5.92 cm/s
Lipophilicity
Log Po/w (iLOGP) : 2.62
Log Po/w (XLOGP3) : 3.06
Log Po/w (WLOGP) : 3.14
Log Po/w (MLOGP) : 3.38
Log Po/w (SILICOS-IT) : 3.05
Consensus Log Po/w : 3.05
Druglikeness
Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55
Water Solubility
Log S (ESOL) : -3.83
Solubility : 0.0437 mg/ml ; 0.000149 mol/l
Class : Soluble
Log S (Ali) : -3.28
Solubility : 0.155 mg/ml ; 0.000526 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.17
Solubility : 0.0199 mg/ml ; 0.0000676 mol/l
Class : Moderately soluble
Medicinal Chemistry
PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.85
Safety of [ 909389-74-8 ]
Application In Synthesis of [ 909389-74-8 ]
* 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 [ 909389-74-8 ]
1
[ 909389-74-8 ]
4-ethynylpyridine hydrochloride
[ No CAS ]
[ 909389-75-9 ]
Yield Reaction Conditions Operation in experiment
66%
With triethylamine In tetrahydrofuran at 60℃; for 16h;
66%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) ; triethylamine In tetrahydrofuran at 60℃; for 16h;
65.3%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) ; triethylamine In tetrahydrofuran at 60℃;
Reference：
[1]Yang, Hai-Bo; Das, Neeladri; Huang, Feihe; Hawkridge, Adam M.; Muddiman, David C.; Stang, Peter J.
[Journal of the American Chemical Society, 2006, vol. 128, # 31, p. 10014 - 10015]
[2]Yang, Hai-Bo; Hawkridge, Adam M.; Huang, Songping D.; Das, Neeladri; Bunge, Scott D.; Muddiman, David C.; Stang, Peter J.
[Journal of the American Chemical Society, 2007, vol. 129, # 7, p. 2120 - 2129]
[3]Jia, Pei-Pei; Xu, Lin; Hu, Yi-Xiong; Li, Wei-Jian; Wang, Xu-Qing; Ling, Qing-Hui; Shi, Xueliang; Yin, Guang-Qiang; Li, Xiaopeng; Sun, Haitao; Jiang, Yanrong; Yang, Hai-Bo
[Journal of the American Chemical Society, 2021, vol. 143, # 1, p. 399 - 408]
2
[ 626-41-5 ]
[ 108-24-7 ]
[ 909389-74-8 ]
Yield Reaction Conditions Operation in experiment
95%
at 70℃; for 2h;
93%
With dmap In toluene at 20℃; Inert atmosphere;
92%
at 70℃; for 2h;
92%
at 70℃; for 2h;
92%
at 70℃;
Reference：
[1]Yang, Hai-Bo; Hawkridge, Adam M.; Huang, Songping D.; Das, Neeladri; Bunge, Scott D.; Muddiman, David C.; Stang, Peter J.
[Journal of the American Chemical Society, 2007, vol. 129, # 7, p. 2120 - 2129]
[2]Swain, Jonathan A.; Iadevaia, Giulia; Hunter, Christopher A.
[Journal of the American Chemical Society, 2018, vol. 140, # 36, p. 11526 - 11536]
[3]Yang, Hai-Bo; Das, Neeladri; Huang, Feihe; Hawkridge, Adam M.; Muddiman, David C.; Stang, Peter J.
[Journal of the American Chemical Society, 2006, vol. 128, # 31, p. 10014 - 10015]
[4]Zhou, Fengyan; Li, Shijun; Cook, Timothy R.; He, Zuoli; Stang, Peter J.
[Organometallics, 2014, vol. 33, # 24, p. 7019 - 7022]
[5]Jia, Pei-Pei; Xu, Lin; Hu, Yi-Xiong; Li, Wei-Jian; Wang, Xu-Qing; Ling, Qing-Hui; Shi, Xueliang; Yin, Guang-Qiang; Li, Xiaopeng; Sun, Haitao; Jiang, Yanrong; Yang, Hai-Bo
[Journal of the American Chemical Society, 2021, vol. 143, # 1, p. 399 - 408]
3
[ 909389-74-8 ]
[ 909389-76-0 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: 66 percent / Pd(PPh3 )4; CuI; Et3 N / tetrahydrofuran / 16 h / 60 °C
2: 99 percent / aq. NaHCO3 / methanol / 2 h / 20 °C
Multi-step reaction with 2 steps
1: 66 percent / Et3 N / Pd(PPh3 )4; CuI / tetrahydrofuran / 16 h / 60 °C
2: 95 percent / aq. NaHCO3 / methanol / 2 h / 20 °C
Reference：
[1]Yang, Hai-Bo; Hawkridge, Adam M.; Huang, Songping D.; Das, Neeladri; Bunge, Scott D.; Muddiman, David C.; Stang, Peter J.
[Journal of the American Chemical Society, 2007, vol. 129, # 7, p. 2120 - 2129]
[2]Yang, Hai-Bo; Das, Neeladri; Huang, Feihe; Hawkridge, Adam M.; Muddiman, David C.; Stang, Peter J.
[Journal of the American Chemical Society, 2006, vol. 128, # 31, p. 10014 - 10015]
4
[ 909389-74-8 ]
[ 909389-77-1 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1.1: 66 percent / Pd(PPh3 )4; CuI; Et3 N / tetrahydrofuran / 16 h / 60 °C
2.1: 99 percent / aq. NaHCO3 / methanol / 2 h / 20 °C
3.1: NaH / dimethylformamide / 0.5 h
3.2: 85 percent / dimethylformamide / 2 h / 65 °C
Reference：
[1]Yang, Hai-Bo; Hawkridge, Adam M.; Huang, Songping D.; Das, Neeladri; Bunge, Scott D.; Muddiman, David C.; Stang, Peter J.
[Journal of the American Chemical Society, 2007, vol. 129, # 7, p. 2120 - 2129]
5
[ 909389-74-8 ]
[ 909389-78-2 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1.1: 66 percent / Pd(PPh3 )4; CuI; Et3 N / tetrahydrofuran / 16 h / 60 °C
2.1: 99 percent / aq. NaHCO3 / methanol / 2 h / 20 °C
3.1: NaH / dimethylformamide / 0.5 h
3.2: 89 percent / dimethylformamide / 2 h / 65 °C
Reference：
[1]Yang, Hai-Bo; Hawkridge, Adam M.; Huang, Songping D.; Das, Neeladri; Bunge, Scott D.; Muddiman, David C.; Stang, Peter J.
[Journal of the American Chemical Society, 2007, vol. 129, # 7, p. 2120 - 2129]
6
[ 909389-74-8 ]
[ 909389-79-3 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1.1: 66 percent / Pd(PPh3 )4; CuI; Et3 N / tetrahydrofuran / 16 h / 60 °C
2.1: 99 percent / aq. NaHCO3 / methanol / 2 h / 20 °C
3.1: NaH / dimethylformamide / 0.5 h
3.2: 87 percent / dimethylformamide / 2 h / 65 °C
Reference：
[1]Yang, Hai-Bo; Hawkridge, Adam M.; Huang, Songping D.; Das, Neeladri; Bunge, Scott D.; Muddiman, David C.; Stang, Peter J.
[Journal of the American Chemical Society, 2007, vol. 129, # 7, p. 2120 - 2129]
7
[ 909389-74-8 ]
C28 H20 N2 O
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: 66 percent / Et3 N / Pd(PPh3 )4; CuI / tetrahydrofuran / 16 h / 60 °C
2: 95 percent / aq. NaHCO3 / methanol / 2 h / 20 °C
3: 85 percent / NaH / dimethylformamide / 65 °C
Reference：
[1]Yang, Hai-Bo; Das, Neeladri; Huang, Feihe; Hawkridge, Adam M.; Muddiman, David C.; Stang, Peter J.
[Journal of the American Chemical Society, 2006, vol. 128, # 31, p. 10014 - 10015]
8
[ 909389-74-8 ]
C42 H32 N2 O3
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: 66 percent / Et3 N / Pd(PPh3 )4; CuI / tetrahydrofuran / 16 h / 60 °C
2: 95 percent / aq. NaHCO3 / methanol / 2 h / 20 °C
3: 89 percent / NaH / dimethylformamide / 65 °C
Reference：
[1]Yang, Hai-Bo; Das, Neeladri; Huang, Feihe; Hawkridge, Adam M.; Muddiman, David C.; Stang, Peter J.
[Journal of the American Chemical Society, 2006, vol. 128, # 31, p. 10014 - 10015]
9
[ 909389-74-8 ]
C70 H56 N2 O7
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: 66 percent / Et3 N / Pd(PPh3 )4; CuI / tetrahydrofuran / 16 h / 60 °C
2: 95 percent / aq. NaHCO3 / methanol / 2 h / 20 °C
3: 87 percent / NaH / dimethylformamide / 65 °C
Reference：
[1]Yang, Hai-Bo; Das, Neeladri; Huang, Feihe; Hawkridge, Adam M.; Muddiman, David C.; Stang, Peter J.
[Journal of the American Chemical Society, 2006, vol. 128, # 31, p. 10014 - 10015]
10
[ 909389-74-8 ]
[ 1066-54-2 ]
[ 1020182-87-9 ]
Yield Reaction Conditions Operation in experiment
86%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) ; triethylamine In toluene at 110℃; for 0.5h; Microwave irradiation; Inert atmosphere;
80%
With triethylamine In tetrahydrofuran at 20℃; for 16h;
Reference：
[1]Swain, Jonathan A.; Iadevaia, Giulia; Hunter, Christopher A.
[Journal of the American Chemical Society, 2018, vol. 140, # 36, p. 11526 - 11536]
[2]Ghosh, Koushik; Yang, Hai-Bo; Northrop, Brian H.; Lyndon, Matthew M.; Zheng, Yao-Rong; Muddiman, David C.; Stang, Peter J.
[Journal of the American Chemical Society, 2008, vol. 130, # 15, p. 5320 - 5334]
11
[ 626-41-5 ]
[ 75-36-5 ]
[ 909389-74-8 ]
Yield Reaction Conditions Operation in experiment
92%
With pyridine; In dichloromethane; at 0 - 20℃;Inert atmosphere;
To a stirred solution of compound XLVIII-1 (10.00 g, 39.69 mmol) in DCM (20 mL) and Py (50 mL) was added dropwise acetyl chloride (3.73 g, 47.51 mmol) at 0 °C under argon. After the addition, the solution was stirred overnight at room temperature. TLC monitored the reaction. After completion of the reaction, the mixture was poured into ice/water (100 mL), extract with DCM (50 mL x 3), the combined organic layers were dried over Na2S04, concentrated in vacuo. The residue was purified by column chromatography (PE:EA = 100: 1) to afford compound XLVIII-2 (11.67 g , yield: 92percent).
12
[ 909389-74-8 ]
[ 669767-20-8 ]
Yield Reaction Conditions Operation in experiment
81.25%
With aluminum (III) chloride at 160℃; for 3h; Inert atmosphere;
XLVIII
A stirred solution of compound XLVIII-2 (8.00 g, 54.43 mmol) and A1C13 (7.26 g, 54.43 mmol) was heated to 160 °C for 3 hours under argon. The solution was quenched with water, extract with EtOAc (60 mL x 3), the combined organic layers were dried over Na2S04, concentrated in vacuo, and purified by chromatography (PE:EA = 50: 1) to afford compound XLVIII-3 (6.5 g, yield 81.25%). 1H NMR (400MHz, DMSO-d6) ^10.94 (s, 1 H), 7.32 (s, 1H), 7.07 (s, 1 H), 2.43 (s, 3 H).
13
[ 909389-74-8 ]
[ 1423702-17-3 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: aluminum (III) chloride / 3 h / 160 °C / Inert atmosphere
2: sodium carbonate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere
14
[ 909389-74-8 ]
[ 1423702-20-8 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: aluminum (III) chloride / 3 h / 160 °C / Inert atmosphere
2: sodium carbonate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere
3: pyridine; hydroxylamine hydrochloride / 6 h / 130 °C / Inert atmosphere
15
[ 909389-74-8 ]
[ 1423702-22-0 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: aluminum (III) chloride / 3 h / 160 °C / Inert atmosphere
2: sodium carbonate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere
3: pyridine; hydroxylamine hydrochloride / 6 h / 130 °C / Inert atmosphere
4: N,N`-dimethylethylenediamine; sodium t-butanolate; copper(l) iodide / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere
16
[ 909389-74-8 ]
[ 1423702-25-3 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 5 steps
1: aluminum (III) chloride / 3 h / 160 °C / Inert atmosphere
2: sodium carbonate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere
3: pyridine; hydroxylamine hydrochloride / 6 h / 130 °C / Inert atmosphere
4: N,N`-dimethylethylenediamine; sodium t-butanolate; copper(l) iodide / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere
5: boron tribromide / dichloromethane / 0 °C / Inert atmosphere
17
[ 909389-74-8 ]
[ 1423702-28-6 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 6 steps
1: aluminum (III) chloride / 3 h / 160 °C / Inert atmosphere
2: sodium carbonate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere
3: pyridine; hydroxylamine hydrochloride / 6 h / 130 °C / Inert atmosphere
4: N,N`-dimethylethylenediamine; sodium t-butanolate; copper(l) iodide / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere
5: boron tribromide / dichloromethane / 0 °C / Inert atmosphere
6: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; 1,2-dimethoxyethane / 80 °C / Inert atmosphere
18
[ 909389-74-8 ]
[ 1423702-31-1 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 7 steps
1: aluminum (III) chloride / 3 h / 160 °C / Inert atmosphere
2: sodium carbonate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere
3: pyridine; hydroxylamine hydrochloride / 6 h / 130 °C / Inert atmosphere
4: N,N`-dimethylethylenediamine; sodium t-butanolate; copper(l) iodide / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere
5: boron tribromide / dichloromethane / 0 °C / Inert atmosphere
6: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; 1,2-dimethoxyethane / 80 °C / Inert atmosphere
7: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
19
[ 909389-74-8 ]
[ 1423702-34-4 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 8 steps
1: aluminum (III) chloride / 3 h / 160 °C / Inert atmosphere
2: sodium carbonate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere
3: pyridine; hydroxylamine hydrochloride / 6 h / 130 °C / Inert atmosphere
4: N,N`-dimethylethylenediamine; sodium t-butanolate; copper(l) iodide / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere
5: boron tribromide / dichloromethane / 0 °C / Inert atmosphere
6: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; 1,2-dimethoxyethane / 80 °C / Inert atmosphere
7: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
8: palladium diacetate; caesium carbonate; Benzophenone imine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / tetrahydrofuran / 80 °C / Inert atmosphere
20
[ 909389-74-8 ]
[ 1423690-66-7 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 9 steps
1.1: aluminum (III) chloride / 3 h / 160 °C / Inert atmosphere
2.1: sodium carbonate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere
3.1: pyridine; hydroxylamine hydrochloride / 6 h / 130 °C / Inert atmosphere
4.1: N,N`-dimethylethylenediamine; sodium t-butanolate; copper(l) iodide / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere
5.1: boron tribromide / dichloromethane / 0 °C / Inert atmosphere
6.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; 1,2-dimethoxyethane / 80 °C / Inert atmosphere
7.1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
8.1: palladium diacetate; caesium carbonate; Benzophenone imine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / tetrahydrofuran / 80 °C / Inert atmosphere
9.1: pyridine / 1,2-dichloro-ethane / 1 h / 0 - 20 °C / Inert atmosphere
9.2: 80 °C / Inert atmosphere
21
[ 909389-74-8 ]
[ 1423684-81-4 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 10 steps
1.1: aluminum (III) chloride / 3 h / 160 °C / Inert atmosphere
2.1: sodium carbonate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere
3.1: pyridine; hydroxylamine hydrochloride / 6 h / 130 °C / Inert atmosphere
4.1: N,N`-dimethylethylenediamine; sodium t-butanolate; copper(l) iodide / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere
5.1: boron tribromide / dichloromethane / 0 °C / Inert atmosphere
6.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; 1,2-dimethoxyethane / 80 °C / Inert atmosphere
7.1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
8.1: palladium diacetate; caesium carbonate; Benzophenone imine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / tetrahydrofuran / 80 °C / Inert atmosphere
9.1: pyridine / 1,2-dichloro-ethane / 1 h / 0 - 20 °C / Inert atmosphere
9.2: 80 °C / Inert atmosphere
10.1: lithium hydroxide; water / methanol / 60 °C / Inert atmosphere
10.2: Acidic conditions
22
[ 909389-74-8 ]
[ 1066-54-2 ]
C12 H8 O2
[ No CAS ]
Yield Reaction Conditions Operation in experiment
82%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) ; triethylamine In tetrahydrofuran at 60℃;
23
[ 909389-74-8 ]
C34 H30 N2 O10
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1.1: tetrakis(triphenylphosphine) palladium(0) ; copper(l) iodide; triethylamine / tetrahydrofuran / 60 °C
2.1: potassium hydroxide / methanol / 24 h
3.1: dichloromethane / 0.5 h / Molecular sieve; Inert atmosphere
3.2: 3 h / 0 °C / Molecular sieve; Inert atmosphere
4.1: tetrakis(triphenylphosphine) palladium(0) ; copper(l) iodide; triethylamine / tetrahydrofuran / 24 h / 60 °C / Schlenk technique; Inert atmosphere
24
[ 909389-74-8 ]
C26 H22 N2 O6
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 5 steps
1.1: tetrakis(triphenylphosphine) palladium(0) ; copper(l) iodide; triethylamine / tetrahydrofuran / 60 °C
2.1: potassium hydroxide / methanol / 24 h
3.1: dichloromethane / 0.5 h / Molecular sieve; Inert atmosphere
3.2: 3 h / 0 °C / Molecular sieve; Inert atmosphere
4.1: tetrakis(triphenylphosphine) palladium(0) ; copper(l) iodide; triethylamine / tetrahydrofuran / 16 h / 60 °C / Schlenk technique; Inert atmosphere
5.1: sodium methylate / methanol / 12 h / 20 °C
25
[ 909389-74-8 ]
C26 H22 N2 O6
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 5 steps
1.1: tetrakis(triphenylphosphine) palladium(0) ; copper(l) iodide; triethylamine / tetrahydrofuran / 60 °C
2.1: potassium hydroxide / methanol / 24 h
3.1: dichloromethane / 0.5 h / Molecular sieve; Inert atmosphere
3.2: 3 h / 0 °C / Molecular sieve; Inert atmosphere
4.1: tetrakis(triphenylphosphine) palladium(0) ; copper(l) iodide; triethylamine / tetrahydrofuran / 24 h / 60 °C / Schlenk technique; Inert atmosphere
5.1: sodium methylate / methanol / 12 h / 20 °C
26
[ 909389-74-8 ]
C26 H22 N2 O6
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 5 steps
1.1: tetrakis(triphenylphosphine) palladium(0) ; copper(l) iodide; triethylamine / tetrahydrofuran / 60 °C
2.1: potassium hydroxide / methanol / 24 h
3.1: dichloromethane / 0.5 h / Molecular sieve; Inert atmosphere
3.2: 3 h / 0 °C / Molecular sieve; Inert atmosphere
4.1: tetrakis(triphenylphosphine) palladium(0) ; copper(l) iodide; triethylamine / tetrahydrofuran / 24 h / 60 °C / Schlenk technique; Inert atmosphere
5.1: sodium methylate / methanol / 12 h / 20 °C
27
[ 909389-74-8 ]
[ 918826-08-1 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: tetrakis(triphenylphosphine) palladium(0) ; copper(l) iodide; triethylamine / tetrahydrofuran / 60 °C
2: potassium hydroxide / methanol / 24 h
28
[ 909389-74-8 ]
C24 H24 O10
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1.1: tetrakis(triphenylphosphine) palladium(0) ; copper(l) iodide; triethylamine / tetrahydrofuran / 60 °C
2.1: potassium hydroxide / methanol / 24 h
3.1: dichloromethane / 0.5 h / Molecular sieve; Inert atmosphere
3.2: 3 h / 0 °C / Molecular sieve; Inert atmosphere
29
[ 909389-74-8 ]
C24 H24 O10
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1.1: tetrakis(triphenylphosphine) palladium(0) ; copper(l) iodide; triethylamine / tetrahydrofuran / 60 °C
2.1: potassium hydroxide / methanol / 24 h
3.1: dichloromethane / 0.5 h / Molecular sieve; Inert atmosphere
3.2: 3 h / 0 °C / Molecular sieve; Inert atmosphere
30
[ 909389-74-8 ]
C24 H24 O10
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1.1: tetrakis(triphenylphosphine) palladium(0) ; copper(l) iodide; triethylamine / tetrahydrofuran / 60 °C
2.1: potassium hydroxide / methanol / 24 h
3.1: dichloromethane / 0.5 h / Molecular sieve; Inert atmosphere
3.2: 3 h / 0 °C / Molecular sieve; Inert atmosphere
31
[ 909389-74-8 ]
C36 H40 O18
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1.1: tetrakis(triphenylphosphine) palladium(0) ; copper(l) iodide; triethylamine / tetrahydrofuran / 60 °C
2.1: potassium hydroxide / methanol / 24 h
3.1: dichloromethane / 0.5 h / Molecular sieve; Inert atmosphere
3.2: 3 h / 0 °C / Molecular sieve; Inert atmosphere
32
[ 909389-74-8 ]
C34 H30 N2 O10
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1.1: tetrakis(triphenylphosphine) palladium(0) ; copper(l) iodide; triethylamine / tetrahydrofuran / 60 °C
2.1: potassium hydroxide / methanol / 24 h
3.1: dichloromethane / 0.5 h / Molecular sieve; Inert atmosphere
3.2: 3 h / 0 °C / Molecular sieve; Inert atmosphere
4.1: tetrakis(triphenylphosphine) palladium(0) ; copper(l) iodide; triethylamine / tetrahydrofuran / 16 h / 60 °C / Schlenk technique; Inert atmosphere
33
[ 909389-74-8 ]
C34 H30 N2 O10
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1.1: tetrakis(triphenylphosphine) palladium(0) ; copper(l) iodide; triethylamine / tetrahydrofuran / 60 °C
2.1: potassium hydroxide / methanol / 24 h
3.1: dichloromethane / 0.5 h / Molecular sieve; Inert atmosphere
3.2: 3 h / 0 °C / Molecular sieve; Inert atmosphere
4.1: tetrakis(triphenylphosphine) palladium(0) ; copper(l) iodide; triethylamine / tetrahydrofuran / 24 h / 60 °C / Schlenk technique; Inert atmosphere
34
[ 3240-34-4 ]
[ 108-36-1 ]
[ 36914-79-1 ]
[ 28165-72-2 ]
[ 909389-74-8 ]
Yield Reaction Conditions Operation in experiment
Stage #1: [bis(acetoxy)iodo]benzene With palladium diacetate; acetic anhydride; acetic acid at 20℃; for 0.00416667h;
Stage #2: 1,3-dibromobenzene at 100℃; for 14h; Sealed tube; Overall yield = 86 %Chromat.;
35
[ 3240-34-4 ]
[ 108-36-1 ]
[ 36914-79-1 ]
[ 909389-74-8 ]
Yield Reaction Conditions Operation in experiment
Stage #1: [bis(acetoxy)iodo]benzene With 6-fluoropyridine-2-carboxylic acid; palladium diacetate; acetic anhydride; acetic acid at 20℃; for 0.00416667h;
Stage #2: 1,3-dibromobenzene at 100℃; for 14h; Sealed tube; Overall yield = 86 %Chromat.;
36
[ 108-22-5 ]
[ 626-41-5 ]
[ 909389-74-8 ]
Yield Reaction Conditions Operation in experiment
99%
With iron(III) trifluoromethanesulfonate at 20℃; for 5h; Schlenk technique;
37
[ 909389-74-8 ]
[ 1066-54-2 ]
[ 918826-08-1 ]
Yield Reaction Conditions Operation in experiment
98%
Stage #1: acetic acid 3,5-dibromo-phenyl ester; trimethylsilylacetylene With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 60℃; for 12h; Inert atmosphere;
Stage #2: With potassium hydroxide In tetrahydrofuran; methanol; water at 20℃; for 12h;
Stage #1: acetic acid 3,5-dibromo-phenyl ester; trimethylsilylacetylene With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine In tetrahydrofuran at 40℃; for 24h;
Stage #2: With sodium hydroxide In tetrahydrofuran; methanol; water for 5h; Inert atmosphere;
Reference：
[1]Zhang, Xu; Moku, Balakrishna; Leng, Jing; Rakesh; Qin, Hua-Li
[European Journal of Organic Chemistry, 2019, vol. 2019, # 8, p. 1763 - 1769]
[2]Chen, Yu; Tan, Ying; Tan, Chunyan; Lu, Yunpeng; Chen, Yuzong; Jiang, Yuyang
[Organic and Biomolecular Chemistry, 2019, vol. 17, # 10, p. 2635 - 2639]
38
[ 626-41-5 ]
[ 909389-74-8 ]
Yield Reaction Conditions Operation in experiment
94%
With acetic anhydride at 70℃; for 2h;
39
[ 909389-74-8 ]
C13 H11 O4 S(1-) *K(1+)
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1.1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine / tetrahydrofuran / 24 h / 40 °C
1.2: 5 h / Inert atmosphere
2.1: potassium hydroxide / ethanol / 24 h / 20 °C
Reference：
[1]Chen, Yu; Tan, Ying; Tan, Chunyan; Lu, Yunpeng; Chen, Yuzong; Jiang, Yuyang
[Organic and Biomolecular Chemistry, 2019, vol. 17, # 10, p. 2635 - 2639]
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