Alternatived Products of [ 1305322-97-7 ]
Product Details of [ 1305322-97-7 ]
CAS No. : 1305322-97-7
MDL No. : MFCD18914516
Formula :
C6 H3 BrClFO
Boiling Point : -
Linear Structure Formula : -
InChI Key : GXMIWRKHBJSAJB-UHFFFAOYSA-N
M.W :
225.44
Pubchem ID : 54759056
Synonyms :
Calculated chemistry of [ 1305322-97-7 ]
Physicochemical Properties
Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 41.13
TPSA : 20.23 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) : -5.55 cm/s
Lipophilicity
Log Po/w (iLOGP) : 2.0
Log Po/w (XLOGP3) : 2.99
Log Po/w (WLOGP) : 3.37
Log Po/w (MLOGP) : 3.26
Log Po/w (SILICOS-IT) : 3.12
Consensus Log Po/w : 2.95
Druglikeness
Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55
Water Solubility
Log S (ESOL) : -3.57
Solubility : 0.0613 mg/ml ; 0.000272 mol/l
Class : Soluble
Log S (Ali) : -3.08
Solubility : 0.188 mg/ml ; 0.000834 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.58
Solubility : 0.0597 mg/ml ; 0.000265 mol/l
Class : Soluble
Medicinal Chemistry
PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.88
Safety of [ 1305322-97-7 ]
Application In Synthesis of [ 1305322-97-7 ]
* 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 [ 1305322-97-7 ]
1
[ 1305322-97-7 ]
[ 1802413-40-6 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 90 °C
2: tris-(dibenzylideneacetone)dipalladium(0) ; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate / tetrahydrofuran / 8 h / 60 °C / Inert atmosphere
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 90 °C
2: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) / tetrahydrofuran / 8 h / 60 °C / Inert atmosphere
2
[ 1305322-97-7 ]
[ 1802413-42-8 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 90 °C
2.1: tris-(dibenzylideneacetone)dipalladium(0) ; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate / tetrahydrofuran / 8 h / 60 °C / Inert atmosphere
3.1: ammonium acetate; sodium cyanoborohydride / methanol / 12 h / 20 °C
3.2: 2 h
Multi-step reaction with 3 steps
1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 90 °C
2: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) / tetrahydrofuran / 8 h / 60 °C / Inert atmosphere
3: sodium cyanoborohydride; methanol; ammonium acetate / 12 h / 20 °C
3
[ 1305322-97-7 ]
[ 1802413-43-9 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 90 °C
2.1: tris-(dibenzylideneacetone)dipalladium(0) ; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate / tetrahydrofuran / 8 h / 60 °C / Inert atmosphere
3.1: ammonium acetate; sodium cyanoborohydride / methanol / 12 h / 20 °C
3.2: 2 h
4.1: 1,4-dioxane / 12 h / Reflux
Multi-step reaction with 4 steps
1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 90 °C
2: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) / tetrahydrofuran / 8 h / 60 °C / Inert atmosphere
3: sodium cyanoborohydride; methanol; ammonium acetate / 12 h / 20 °C
4: 1,4-dioxane / 12 h / Reflux
4
[ 1305322-97-7 ]
[ 1802413-44-0 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 5 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 90 °C
2.1: tris-(dibenzylideneacetone)dipalladium(0) ; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate / tetrahydrofuran / 8 h / 60 °C / Inert atmosphere
3.1: ammonium acetate; sodium cyanoborohydride / methanol / 12 h / 20 °C
3.2: 2 h
4.1: 1,4-dioxane / 12 h / Reflux
5.1: trichlorophosphate / acetonitrile / 3 h / 0 - 5 °C / Reflux
Multi-step reaction with 5 steps
1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 90 °C
2: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) / tetrahydrofuran / 8 h / 60 °C / Inert atmosphere
3: sodium cyanoborohydride; methanol; ammonium acetate / 12 h / 20 °C
4: 1,4-dioxane / 12 h / Reflux
5: trichlorophosphate / acetonitrile / 3 h / 0 °C / Reflux
5
[ 1305322-97-7 ]
[ 1802413-45-1 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 6 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 90 °C
2.1: tris-(dibenzylideneacetone)dipalladium(0) ; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate / tetrahydrofuran / 8 h / 60 °C / Inert atmosphere
3.1: ammonium acetate; sodium cyanoborohydride / methanol / 12 h / 20 °C
3.2: 2 h
4.1: 1,4-dioxane / 12 h / Reflux
5.1: trichlorophosphate / acetonitrile / 3 h / 0 - 5 °C / Reflux
6.1: ethanol / Reflux
Multi-step reaction with 6 steps
1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 90 °C
2: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) / tetrahydrofuran / 8 h / 60 °C / Inert atmosphere
3: sodium cyanoborohydride; methanol; ammonium acetate / 12 h / 20 °C
4: 1,4-dioxane / 12 h / Reflux
5: trichlorophosphate / acetonitrile / 3 h / 0 °C / Reflux
6: ethanol / Reflux
6
[ 1305322-97-7 ]
[ 1802413-46-2 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 7 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 90 °C
2.1: tris-(dibenzylideneacetone)dipalladium(0) ; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate / tetrahydrofuran / 8 h / 60 °C / Inert atmosphere
3.1: ammonium acetate; sodium cyanoborohydride / methanol / 12 h / 20 °C
3.2: 2 h
4.1: 1,4-dioxane / 12 h / Reflux
5.1: trichlorophosphate / acetonitrile / 3 h / 0 - 5 °C / Reflux
6.1: ethanol / Reflux
7.1: chloranil / 1,2-dimethoxyethane / 2 h / Reflux
Multi-step reaction with 7 steps
1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 90 °C
2: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) / tetrahydrofuran / 8 h / 60 °C / Inert atmosphere
3: sodium cyanoborohydride; methanol; ammonium acetate / 12 h / 20 °C
4: 1,4-dioxane / 12 h / Reflux
5: trichlorophosphate / acetonitrile / 3 h / 0 °C / Reflux
6: ethanol / Reflux
7: chloranil / 1,2-dimethoxyethane / 2 h / Reflux
7
[ 1305322-97-7 ]
[ 1802407-62-0 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 8 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 90 °C
2.1: tris-(dibenzylideneacetone)dipalladium(0) ; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate / tetrahydrofuran / 8 h / 60 °C / Inert atmosphere
3.1: ammonium acetate; sodium cyanoborohydride / methanol / 12 h / 20 °C
3.2: 2 h
4.1: 1,4-dioxane / 12 h / Reflux
5.1: trichlorophosphate / acetonitrile / 3 h / 0 - 5 °C / Reflux
6.1: ethanol / Reflux
7.1: chloranil / 1,2-dimethoxyethane / 2 h / Reflux
8.1: lithium hydroxide / methanol; tetrahydrofuran / 4 h / 20 °C
Multi-step reaction with 8 steps
1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 90 °C
2: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) / tetrahydrofuran / 8 h / 60 °C / Inert atmosphere
3: sodium cyanoborohydride; methanol; ammonium acetate / 12 h / 20 °C
4: 1,4-dioxane / 12 h / Reflux
5: trichlorophosphate / acetonitrile / 3 h / 0 °C / Reflux
6: ethanol / Reflux
7: chloranil / 1,2-dimethoxyethane / 2 h / Reflux
8: lithium hydroxide; water / methanol; tetrahydrofuran / 4 h / 20 °C
8
[ 36865-41-5 ]
[ 1305322-97-7 ]
[ 1802413-39-3 ]
Yield Reaction Conditions Operation in experiment
5.6 g
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 5h;
137.1 Preparation of 5-bromo-1-chloro-2-fluoro-3-(3-methoxypropoxy)benzene
To a solution of 5-bromo-3-chloro-2-fluoro-phenol (5 g, 22.5 mmol, TCI) in DMF (25 ml) was added potassium carbonate (6.2 g, 45 mmol) and 1-bromo-3-methoxy-propane (42 g, 27 mmol, Accela). The resulting mixture was heated at 90° C. for 5 h. After being cooled to room temperature, the mixture was poured into water (200 mL) and the aqueous solution was extracted with ethyl acetate (200 mL*2). The organic layers were combined and washed with water and brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure to give 5-bromo-1-chloro-2-fluoro-3-(3-methoxypropoxy)benzene (5.6 g) as a red oil which was used directly in the next step without further purification.
5.6 g
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 5h;
137.1 Step 1: Preparation of 5-bromo- 1 -ehloro-2-fluoro-3-(3-methoxypropoxy)benzene
Step 1: Preparation of 5-bromo- 1 -ehloro-2-fluoro-3-(3-methoxypropoxy)benzene To a solution of 5-bromo -3 -chloro-2-fluoro-phenol (5 g, 22.5 mmol, TCI) in DMF (25 ml) was added potassium carbonate (6.2 g, 45 mmol) and l-bromo-3-methoxy-propane (42 g, 27 mmol, Aecela). The resulting mixture was heated at 90 °C for 5 h. After being cooled to room temperature, the mixture was poured into water (200 mL) and the aqueous solution was extracted with ethyl acetate (200 ml 2). The organic layers were combined and washed with water and brine, dried over anhydrous a.>SO.i and concentrated under reduced pressure to give 5-bromo- 1- chloro-2-fluoro-3-(3-methoxypropoxy)benzene (5.6 g) as a red oil which was used directly in the next step without further purification.
9
[ 1305322-97-7 ]
[ CAS Unavailable ]
[ CAS Unavailable ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 9 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 90 °C
2.1: tris-(dibenzylideneacetone)dipalladium(0) ; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate / tetrahydrofuran / 8 h / 60 °C / Inert atmosphere
3.1: ammonium acetate; sodium cyanoborohydride / methanol / 12 h / 20 °C
3.2: 2 h
4.1: 1,4-dioxane / 12 h / Reflux
5.1: trichlorophosphate / acetonitrile / 3 h / 0 - 5 °C / Reflux
6.1: ethanol / Reflux
7.1: chloranil / 1,2-dimethoxyethane / 2 h / Reflux
8.1: lithium hydroxide / methanol; tetrahydrofuran / 4 h / 20 °C
9.1: Resolution of racemate
Multi-step reaction with 9 steps
1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 90 °C
2: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) / tetrahydrofuran / 8 h / 60 °C / Inert atmosphere
3: sodium cyanoborohydride; methanol; ammonium acetate / 12 h / 20 °C
4: 1,4-dioxane / 12 h / Reflux
5: trichlorophosphate / acetonitrile / 3 h / 0 °C / Reflux
6: ethanol / Reflux
7: chloranil / 1,2-dimethoxyethane / 2 h / Reflux
8: lithium hydroxide; water / methanol; tetrahydrofuran / 4 h / 20 °C
9: Resolution of racemate
10
[ 1305322-97-7 ]
[ 74-88-4 ]
[ 1784628-41-6 ]
Yield Reaction Conditions Operation in experiment
With potassium carbonate In acetonitrile at 100℃; for 0.166667h; Microwave irradiation;
1.2.25
5-Bromo-3-chloro-2-fluorophenol (113 mg, 0.5 mmol, 1.0 eq.) is dissolved in MeCN (1 mL) in a microwave vial. Iodomethane (94 µL, 1.5 mmol, 3.0 eq.) and potassium carbonate (138 mg, 1.0 mmol, 2.0 eq.) are successively added. The vial is submitted to microwave irradiation at 100°C for 10 min. The mixture is filtered and the salts are washed with EtOAc. The filtrate is then partitioned between water and EtOAc. The organic phase is dried over Na2SO4, filtered and concentrated in vacuo to afford the expected product, which is used as such in the next step.
With potassium carbonate In acetonitrile at 100℃; for 0.166667h; Microwave irradiation;
2.9 2.9. Synthesis of mt 129
102651 5-Bromo-3-chloro-2-fluorophenol(113 mg, 0.5 mmol, 1.0 eq.) is dissolved in MeCN (1 mL) in a microwave vial. lodomethane (94 jiL, 1.5 mmol, 3.0 eq.) and potassium carbonate (138 mg, 1.0 mmol, 2.0 eq.) are successively added. The vial is submitted to microwave irradiation at 100°C for 10 mm. The mixture is filtered and the salts are washed with EtOAc. The filtrate is then partitioned between water and EtOAc. The organic phase is dried over Na2SO4, filtered and concentrated in vacuo to afford the expected product, which is used as such in the next step.
11
[ 50-00-0 ]
[ 1305322-97-7 ]
[ 2648668-16-8 ]
Yield Reaction Conditions Operation in experiment
73.1%
With water; sodium hydroxide at 20 - 45℃;
Synthesis of 5-bromo-3-chloro-2-fluoro-4-(hydroxymethyl)phenol (Intermediate A37)
To a solution of NaOH (2.0 g, 49.1 mmol) in H2O (100 mL) at rt was added Intermediate A36 (10.0 g, 40.6 mmol). The mixture was heated to 45oC and formaldehyde (3.3 mL of 37% aqueous, 40.6 mmol) was added dropwise. The mixture was stirred at 45°C overnight. The reaction was cooled to rt and diluted with water (50 mL), then acidified with 1N HCl to pH~5-6 and extracted with EtOAc (30 mL*3). The combined organic phase was washed with brine (100 mL), dried over Na2SO4 and concentrated in vacuo. The crude product was purified by silica gel column chromatography (EtOAc/pet. ether =1/50 to 1/5) to afford Intermediate A37 (7.6 g, 73.1% yield) as a white solid. TLC: EtOAc/pet. ether =1/5(v/v), Rf=0.20 1H NMR: (400 MHz, DMSO-d6) δ 10.87 (s, 1H), 7.18 (d, J = 8.0 Hz, 1H), 5.12 (t, J = 5.2 Hz, 1H), 4.62 - 4.58 (m, 2H).
12
[ 60811-21-4 ]
[ 1305322-97-7 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: 4,4'-di-tert-butyl-2,2'-bipyridine; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer / tetrahydrofuran / 80 °C / Inert atmosphere
2: dihydrogen peroxide / tetrahydrofuran; water / 2 h / 20 °C
13
[ 2648668-14-6 ]
[ 1305322-97-7 ]
Yield Reaction Conditions Operation in experiment
99.5%
With dihydrogen peroxide In tetrahydrofuran; water at 20℃; for 2h;
Synthesis of 5-bromo-3-chloro-2-fluorophenol (Intermediate A36)
To a solution of Intermediate A35 (14.5 g, 43.2 mmol) in THF (100 mL) at rt was added aqueous H2O2 (24.5 mL of 37% aqueous solution, 216 mmol); the mixture was stirred at rt for 2h. Na2S2O3 (8.0 g) was added; the mixture was stirred for 20 min, then extracted with EtOAc (50 mL*3). The combined organic phase was washed with brine (100 mL), dried over Na2SO4 and concentrated in vacuo to afford Intermediate A36 (9.7 g, 99.5% yield) as a yellow liquid. TLC: EtOAc/pet. ether =1/10(v/v), Rf=0.5
14
[ 1305322-97-7 ]
[ 2648669-03-6 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: sodium hydroxide; water / 20 - 45 °C
2: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C
3: thionyl chloride / dichloromethane / 1 h / 20 °C
4: zinc(II) chloride / 1,2-dichloro-ethane / 20 - 85 °C
15
[ 1305322-97-7 ]
[ 2648666-57-1 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 5 steps
1: sodium hydroxide; water / 20 - 45 °C
2: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C
3: thionyl chloride / dichloromethane / 1 h / 20 °C
4: zinc(II) chloride / 1,2-dichloro-ethane / 20 - 85 °C
5: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2 Cl2 / water; 1,4-dioxane / 3 h / 20 - 120 °C / Inert atmosphere; Sealed tube
16
[ 1305322-97-7 ]
[ 2648666-59-3 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 6 steps
1: sodium hydroxide; water / 20 - 45 °C
2: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C
3: thionyl chloride / dichloromethane / 1 h / 20 °C
4: zinc(II) chloride / 1,2-dichloro-ethane / 20 - 85 °C
5: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2 Cl2 / water; 1,4-dioxane / 3 h / 20 - 120 °C / Inert atmosphere; Sealed tube
6: water; lithium hydroxide monohydrate / tetrahydrofuran / 1 h / 20 °C
17
[ 1305322-97-7 ]
[ 2648666-60-6 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 6 steps
1: sodium hydroxide; water / 20 - 45 °C
2: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C
3: thionyl chloride / dichloromethane / 1 h / 20 °C
4: zinc(II) chloride / 1,2-dichloro-ethane / 20 - 85 °C
5: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2 Cl2 / water; 1,4-dioxane / 3 h / 20 - 120 °C / Inert atmosphere; Sealed tube
6: palladium on activated charcoal; hydrogen / tetrahydrofuran / 60 °C
18
[ 1305322-97-7 ]
[ 2648666-61-7 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 7 steps
1: sodium hydroxide; water / 20 - 45 °C
2: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C
3: thionyl chloride / dichloromethane / 1 h / 20 °C
4: zinc(II) chloride / 1,2-dichloro-ethane / 20 - 85 °C
5: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2 Cl2 / water; 1,4-dioxane / 3 h / 20 - 120 °C / Inert atmosphere; Sealed tube
6: palladium on activated charcoal; hydrogen / tetrahydrofuran / 60 °C
7: water; lithium hydroxide monohydrate / tetrahydrofuran / 1 h / 20 °C
19
[ 1305322-97-7 ]
[ 2648666-62-8 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 5 steps
1: sodium hydroxide; water / 20 - 45 °C
2: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C
3: thionyl chloride / dichloromethane / 1 h / 20 °C
4: zinc(II) chloride / 1,2-dichloro-ethane / 20 - 85 °C
5: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2 Cl2 / water; 1,4-dioxane / 2 h / 20 - 120 °C / Inert atmosphere; Sealed tube
20
[ 1305322-97-7 ]
[ 2648666-63-9 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 6 steps
1: sodium hydroxide; water / 20 - 45 °C
2: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C
3: thionyl chloride / dichloromethane / 1 h / 20 °C
4: zinc(II) chloride / 1,2-dichloro-ethane / 20 - 85 °C
5: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2 Cl2 / water; 1,4-dioxane / 2 h / 20 - 120 °C / Inert atmosphere; Sealed tube
6: water; lithium hydroxide monohydrate / tetrahydrofuran / 1 h / 20 °C
21
[ 1305322-97-7 ]
[ 2648666-64-0 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 6 steps
1: sodium hydroxide; water / 20 - 45 °C
2: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C
3: thionyl chloride / dichloromethane / 1 h / 20 °C
4: zinc(II) chloride / 1,2-dichloro-ethane / 20 - 85 °C
5: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2 Cl2 / water; 1,4-dioxane / 2 h / 20 - 120 °C / Inert atmosphere; Sealed tube
6: palladium on activated charcoal; hydrogen / tetrahydrofuran / 60 °C
22
[ 1305322-97-7 ]
[ 2648666-65-1 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 7 steps
1: sodium hydroxide; water / 20 - 45 °C
2: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C
3: thionyl chloride / dichloromethane / 1 h / 20 °C
4: zinc(II) chloride / 1,2-dichloro-ethane / 20 - 85 °C
5: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2 Cl2 / water; 1,4-dioxane / 2 h / 20 - 120 °C / Inert atmosphere; Sealed tube
6: palladium on activated charcoal; hydrogen / tetrahydrofuran / 60 °C
7: water; lithium hydroxide monohydrate / tetrahydrofuran / 1 h / 20 °C
23
[ 1305322-97-7 ]
[ 2648667-69-8 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 7 steps
1.1: sodium hydroxide; water / 20 - 45 °C
2.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C
3.1: thionyl chloride / dichloromethane / 1 h / 20 °C
4.1: zinc(II) chloride / 1,2-dichloro-ethane / 20 - 85 °C
5.1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2 Cl2 / water; 1,4-dioxane / 3 h / 20 - 120 °C / Inert atmosphere; Sealed tube
6.1: water; lithium hydroxide monohydrate / tetrahydrofuran / 1 h / 20 °C
7.1: oxalyl dichloride / dichloromethane / 0.5 h / 0 - 20 °C
7.2: 1 h / 20 °C
24
[ 1305322-97-7 ]
[ 2648667-70-1 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 7 steps
1.1: sodium hydroxide; water / 20 - 45 °C
2.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C
3.1: thionyl chloride / dichloromethane / 1 h / 20 °C
4.1: zinc(II) chloride / 1,2-dichloro-ethane / 20 - 85 °C
5.1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2 Cl2 / water; 1,4-dioxane / 3 h / 20 - 120 °C / Inert atmosphere; Sealed tube
6.1: water; lithium hydroxide monohydrate / tetrahydrofuran / 1 h / 20 °C
7.1: oxalyl dichloride / dichloromethane / 0.5 h / 0 - 20 °C
7.2: 1 h / 20 °C
25
[ 1305322-97-7 ]
[ 2648667-72-3 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 8 steps
1.1: sodium hydroxide; water / 20 - 45 °C
2.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C
3.1: thionyl chloride / dichloromethane / 1 h / 20 °C
4.1: zinc(II) chloride / 1,2-dichloro-ethane / 20 - 85 °C
5.1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2 Cl2 / water; 1,4-dioxane / 3 h / 20 - 120 °C / Inert atmosphere; Sealed tube
6.1: palladium on activated charcoal; hydrogen / tetrahydrofuran / 60 °C
7.1: water; lithium hydroxide monohydrate / tetrahydrofuran / 1 h / 20 °C
8.1: oxalyl dichloride / dichloromethane / 0.5 h / 0 - 20 °C
8.2: 1 h / 20 °C
26
[ 1305322-97-7 ]
[ 2648667-73-4 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 8 steps
1.1: sodium hydroxide; water / 20 - 45 °C
2.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C
3.1: thionyl chloride / dichloromethane / 1 h / 20 °C
4.1: zinc(II) chloride / 1,2-dichloro-ethane / 20 - 85 °C
5.1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2 Cl2 / water; 1,4-dioxane / 3 h / 20 - 120 °C / Inert atmosphere; Sealed tube
6.1: palladium on activated charcoal; hydrogen / tetrahydrofuran / 60 °C
7.1: water; lithium hydroxide monohydrate / tetrahydrofuran / 1 h / 20 °C
8.1: oxalyl dichloride / dichloromethane / 0.5 h / 0 - 20 °C
8.2: 1 h / 20 °C
27
[ 1305322-97-7 ]
[ 2648668-17-9 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: sodium hydroxide; water / 20 - 45 °C
2: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C
28
[ 1305322-97-7 ]
[ 2648668-20-4 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: sodium hydroxide; water / 20 - 45 °C
2: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C
3: thionyl chloride / dichloromethane / 1 h / 20 °C
29
[ 1305322-97-7 ]
[ 611-19-8 ]
[ 1369923-33-0 ]
Yield Reaction Conditions Operation in experiment
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 1h;
Reference：
[1]Zhang, Chun-Hui; Spasov, Krasimir A.; Reilly, Raquel A.; Hollander, Klarissa; Stone, Elizabeth A.; Ippolito, Joseph A.; Liosi, Maria-Elena; Deshmukh, Maya G.; Tirado-Rives, Julian; Zhang, Shuo; Liang, Zhuobin; Miller, Scott J.; Isaacs, Farren; Lindenbach, Brett D.; Anderson, Karen S.; Jorgensen, William L.
[ACS Medicinal Chemistry Letters, 2021, vol. 12, # 8, p. 1325 - 1332]
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