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[ CAS No. 1261739-13-2 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 1261739-13-2
Chemical Structure| 1261739-13-2
Chemical Structure| 1261739-13-2
Structure of 1261739-13-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1261739-13-2 ]

CAS No. :1261739-13-2 MDL No. :MFCD18416520
Formula : C9H10ClNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :YWSZVSFVKKLKOU-UHFFFAOYSA-N
M.W : 199.63 Pubchem ID :71711096
Synonyms :

Calculated chemistry of [ 1261739-13-2 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.33
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 50.3
TPSA : 39.19 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) : -5.81 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.27
Log Po/w (XLOGP3) : 2.4
Log Po/w (WLOGP) : 2.22
Log Po/w (MLOGP) : 1.55
Log Po/w (SILICOS-IT) : 2.64
Consensus Log Po/w : 2.21

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.73
Solubility : 0.369 mg/ml ; 0.00185 mol/l
Class : Soluble
Log S (Ali) : -2.86
Solubility : 0.273 mg/ml ; 0.00137 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.51
Solubility : 0.0611 mg/ml ; 0.000306 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.98

Safety of [ 1261739-13-2 ]

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:

Application In Synthesis of [ 1261739-13-2 ]

* 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 [ 1261739-13-2 ]

[ 1261739-13-2 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 1261739-13-2 ]
  • [ 73183-34-3 ]
  • [ 1859083-96-7 ]
YieldReaction ConditionsOperation in experiment
53% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In toluene at 130℃; for 20h; 2.5 Step 5. Synthesis of ethyl 5-methyl-4-(4, 4,5, 5-tetramethyl- 1,3, 2-dioxaborolan-2- yl)pyridine-2-carboxylate (C 10). A mixture of C9 (16 g, 80 mmol), 4,4,4’,4’,5,5,5’,5’-octamethyl-2,2’-bi-1 3,2- dioxaborolane (30.5 g, 120 mmol), [1,1’- bis(diphenylphosphino)ferrocene]dichloropalladium(ll) (5.86 g, 8.01 mmol), and potassium acetate (28.3 g, 288 mmol) in toluene (1.2 L) was stirred at 130 00 for 20 hours. After filtration of the reaction mixture, the filtrate was concentrated underreduced pressure. The residue was purified by chromatography on silica gel (Gradient:10% to 50% ethyl acetate in petroleum ether) to provide a yellow solid (20 g), which was diluted with petroleum ether (50 mL) and stirred at room temperature for 20 minutes. The solid was collected via filtration to afford the product (8.8 g) as a white solid. The corresponding filtrate was concentrated in vacuo and the residue was purifiedby silica gel chromatography (Gradient: 0% to 30% ethyl acetate in petroleum ether); the isolated material (4.5 g) was washed with petroleum ether (5 mL) to yield additional product (3.5 g) as a white solid. Combined yield: 12.3 g, 42.2 mmol, 53%. 1H NMR (400 MHz, CDCI3) ö 8.57 (5, 1H), 8.39 (5, 1H), 4.48 (q, J=7.2 Hz, 2H), 2.57 (5, 3H), 1.45 (t, J=7.2 Hz, 3H), 1.37 (5, 12H).
  • 2
  • [ 1261739-13-2 ]
  • [ 73183-34-3 ]
  • [ 1859084-29-9 ]
YieldReaction ConditionsOperation in experiment
With tris-(dibenzylideneacetone)dipalladium(0); potassium acetate; tricyclohexylphosphine In 1,4-dioxane at 150℃; for 5.5h; Sealed tube; 8; 9.1 Step 1. Synthesis of [2-(ethoxycarbonyl)-5-methylpyridin-4-yl]boronic acid (C22). A mixture of C9 (680 mg, 3.41 mmol), 4,4,4’,4’,5,5,5’,5’-octamethyl-2,2’-bi-1 3,2-dioxaborolane (1.04 g, 4.10 mmol), tricyclohexylphosphine (48 mg, 0.17 mmol),tris(dibenzylideneacetone)dipalladium(0) (93 mg, 0.10 mmol), and potassium acetate(1.00 g, 10.2 mmol) in 1,4-dioxane (25 mL) was stirred in a sealed vial at 15000 for 5.5hours. The reaction mixture was filtered, and the filtrate (a 1 ,4-dioxane solution of C22)was used directly in the following step.
  • 3
  • [ 64-17-5 ]
  • [ CAS Unavailable ]
  • [ 56961-78-5 ]
  • [ 1261739-13-2 ]
YieldReaction ConditionsOperation in experiment
62% With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; triethylamine at 60℃; for 4h; 2.4 Step 4. Synthesis of ethyl 4-chloro-5-methylpyridine-2-carboxylate (C9). A mixture of 2,4-dichloro-5-methylpyridine (33 g, 0.20 mol), [1,1’-bis(diphenylphosphino)ferrocene]dichloropalladium(ll) (7.45 g, 10.2 mmol), andtriethylamine (61.8 g, 611 mmol) in ethanol (500 mL) was stirred under carbon monoxide (30 psi) at 60 00 for 4 hours. The reaction mixture was filtered, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (Gradient: 10% to 50% ethyl acetate in petroleum ether), providing theproduct as a yellow oil. Yield: 25.0 g, 0.125 mol, 62%. 1H NMR (400 MHz, ODd3) ö8.56 (5, 1H), 8.11 (5, 1H), 4.48 (q, J=7.1 Hz, 2H), 2.44 (5, 3H), 1.44 (t, J=7.1 Hz, 3H).
With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; triethylamine In N,N-dimethyl-formamide at 60℃; for 12h; 129 (3R,7S,E)-7-(3,3-difluorobutyl)-4-ethyl-25,3-dimethyl-10,13-dioxa-4,6-diaza-1(6,8)- [1,2,4]triazolo[1,5-a]pyrazina-2(4,2)-pyridinacyclotridecaphan-5-one (Example 129) To a solution of 2,4-dichloro-5-methylpyridine (15 g,93 mmol) in Ethanol (200 mL) and DMF (40 mL) were added TEA (38.7 mL, 278 mmol) and Pd(dppf)Cl2 (3.39 g, 4.63 mmol). The mixture was stirred at 60 °C under CO (50 psi) for 12 h. The reaction mixture was concentrated and poured into water (500 mL), extracted with EtOAc (200 mL×3). The organic layer was washed with brine (200 mL), dried over Na2SO4 and filtered. The filtrate was concentrated and purified by flash silica gel chromatography (ISCO; 120 g SepaFlash Silica Flash Column, eluent of 50% ethyl acetate/pet. ether gradient) to give ethyl 4-chloro-5- methylpicolinate. LCMS m/z (M+H): 200.0 required, 200.1 found
With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; triethylamine In N,N-dimethyl-formamide at 60℃; for 12h; 129 (3R,7S,E)-7-(3,3-difluorobutyl)-4-ethyl-25,3-dimethyl-10,13-dioxa-4,6-diaza-1(6,8)- [1,2,4]triazolo[1,5-a]pyrazina-2(4,2)-pyridinacyclotridecaphan-5-one (Example 129) To a solution of 2,4-dichloro-5-methylpyridine (15 g,93 mmol) in Ethanol (200 mL) and DMF (40 mL) were added TEA (38.7 mL, 278 mmol) and Pd(dppf)Cl2 (3.39 g, 4.63 mmol). The mixture was stirred at 60 °C under CO (50 psi) for 12 h. The reaction mixture was concentrated and poured into water (500 mL), extracted with EtOAc (200 mL×3). The organic layer was washed with brine (200 mL), dried over Na2SO4 and filtered. The filtrate was concentrated and purified by flash silica gel chromatography (ISCO; 120 g SepaFlash Silica Flash Column, eluent of 50% ethyl acetate/pet. ether gradient) to give ethyl 4-chloro-5- methylpicolinate. LCMS m/z (M+H): 200.0 required, 200.1 found
  • 4
  • [ 1261739-13-2 ]
  • [ 1859081-75-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium acetate; tricyclohexylphosphine; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 5.5 h / 150 °C / Sealed tube 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / water; 1,4-dioxane / 20 h / 80 °C 3: sodium hydroxide; water / methanol / 2 h / 80 °C 4: triethylamine; HATU / dichloromethane / 40 °C
  • 5
  • [ 1261739-13-2 ]
  • [ 1859081-85-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium acetate; tricyclohexylphosphine; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 5.5 h / 150 °C / Sealed tube 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / water; 1,4-dioxane / 20 h / 80 °C 3: sodium hydroxide; water / methanol / 2 h / 80 °C 4: triethylamine; HATU / N,N-dimethyl-formamide / 16 h / 30 °C / Sealed tube
  • 6
  • [ 1261739-13-2 ]
  • [ 1842395-04-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium acetate; tricyclohexylphosphine; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 5.5 h / 150 °C / Sealed tube 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / water; 1,4-dioxane / 20 h / 80 °C 3: sodium hydroxide; water / methanol / 2 h / 80 °C 4: triethylamine; HATU / dichloromethane / 20 °C
  • 7
  • [ 1261739-13-2 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium acetate; tricyclohexylphosphine; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 5.5 h / 150 °C / Sealed tube 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / water; 1,4-dioxane / 20 h / 80 °C 3: sodium hydroxide; water / methanol / 2 h / 80 °C 4: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 16 h / 50 °C / Sealed tube
  • 8
  • [ 1261739-13-2 ]
  • [ 1859082-94-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium acetate; tricyclohexylphosphine; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 5.5 h / 150 °C / Sealed tube 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / water; 1,4-dioxane / 20 h / 80 °C 3.1: sodium hydroxide; water / methanol / 2 h / 80 °C 4.1: Silicycle SiliaBond® carbonate resin / methanol / 20 °C 4.2: 20 °C 5.1: 3-chloro-benzenecarboperoxoic acid
Multi-step reaction with 6 steps 1: potassium acetate; tricyclohexylphosphine; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 5.5 h / 150 °C / Sealed tube 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / water; 1,4-dioxane / 20 h / 80 °C 3: sodium hydroxide; water / methanol / 2 h / 80 °C 4: triethylamine; HATU / dichloromethane / 2 h / 20 °C 5: ammonium hydroxide / ethanol / Resolution of racemate 6: 3-chloro-benzenecarboperoxoic acid
  • 9
  • [ 1261739-13-2 ]
  • [ 1859084-97-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium acetate; tricyclohexylphosphine; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 5.5 h / 150 °C / Sealed tube 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / water; 1,4-dioxane / 20 h / 80 °C 3: sodium hydroxide; water / methanol / 2 h / 80 °C 4: hydrogenchloride / 60 °C
  • 10
  • [ 1261739-13-2 ]
  • [ 1859082-00-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium acetate; tricyclohexylphosphine; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 5.5 h / 150 °C / Sealed tube 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / water; 1,4-dioxane / 20 h / 80 °C 3.1: sodium hydroxide; water / methanol / 2 h / 80 °C 4.1: hydrogenchloride / 60 °C 5.1: trimethylaluminum / toluene; tetrahydrofuran / 16 h / 30 °C 5.2: 80 °C
  • 11
  • [ 1261739-13-2 ]
  • [ 1859085-12-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium acetate; tricyclohexylphosphine; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 5.5 h / 150 °C / Sealed tube 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / water; 1,4-dioxane / 20 h / 80 °C 3: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 1 h / 75 °C / Irradiation
  • 12
  • [ 1261739-13-2 ]
  • [ 1859085-15-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium acetate; tricyclohexylphosphine; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 5.5 h / 150 °C / Sealed tube 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / water; 1,4-dioxane / 20 h / 80 °C 3: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 1 h / 75 °C / Irradiation 4: water / acetone / 3 h / 20 °C
  • 13
  • [ 1261739-13-2 ]
  • [ 1859085-17-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: potassium acetate; tricyclohexylphosphine; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 5.5 h / 150 °C / Sealed tube 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / water; 1,4-dioxane / 20 h / 80 °C 3: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 1 h / 75 °C / Irradiation 4: water / acetone / 3 h / 20 °C 5: N-ethyl-N,N-diisopropylamine; Nonafluorobutanesulfonyl fluoride; triethylamine tris(hydrogen fluoride) / acetonitrile / 1 h / 20 °C
  • 14
  • [ 1261739-13-2 ]
  • [ 1859085-35-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / toluene / 20 h / 130 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / water; 1,4-dioxane / 18 h / 100 °C / Inert atmosphere
  • 15
  • [ 1261739-13-2 ]
  • [ 1859085-38-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / toluene / 20 h / 130 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / water; 1,4-dioxane / 18 h / 100 °C / Inert atmosphere 3: sodium hydroxide; water / 1,4-dioxane / 20 h / 25 °C
  • 16
  • [ 1261739-13-2 ]
  • [ 1859083-03-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / toluene / 20 h / 130 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / water; 1,4-dioxane / 18 h / 100 °C / Inert atmosphere 3.1: sodium hydroxide; water / 1,4-dioxane / 20 h / 25 °C 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / dichloromethane; N,N-dimethyl-formamide / 4 h / 25 °C 4.2: 36.5 h / 25 °C
  • 17
  • [ 1261739-13-2 ]
  • [ 1859085-56-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / toluene / 20 h / 130 °C 2: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; 1,4-dioxane / 2 h / 50 °C / Sealed tube
  • 18
  • [ 1261739-13-2 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / toluene / 20 h / 130 °C 2: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; 1,4-dioxane / 2 h / 50 °C / Sealed tube 3: 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine / N,N-dimethyl-formamide / 60 °C
  • 19
  • [ 1261739-13-2 ]
  • [ 1859085-65-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / toluene / 20 h / 130 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / water; 1,4-dioxane / 8 h / 80 °C
  • 20
  • [ 1261739-13-2 ]
  • [ 1859085-67-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / toluene / 20 h / 130 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / water; 1,4-dioxane / 8 h / 80 °C 3: sodium hydroxide; water / tetrahydrofuran / 16 h / 50 °C
  • 21
  • [ 1261739-13-2 ]
  • [ 1859083-14-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / toluene / 20 h / 130 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / water; 1,4-dioxane / 8 h / 80 °C 3.1: sodium hydroxide; water / tetrahydrofuran / 16 h / 50 °C 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 1 h / 18 °C 4.2: 18 h / 18 °C 4.3: 20 h / 18 °C
  • 22
  • [ 1261739-13-2 ]
  • [ 1859083-98-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / toluene / 20 h / 130 °C 2: sodium hydroxide; water; tetrakis(triphenylphosphine) palladium(0) / acetonitrile / 4 h / 80 °C
  • 23
  • [ 1261739-13-2 ]
  • [ 1859081-44-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / toluene / 20 h / 130 °C 2: sodium hydroxide; water; tetrakis(triphenylphosphine) palladium(0) / acetonitrile / 4 h / 80 °C 3: triethylamine; HATU / dichloromethane / 40 h / 25 °C
  • 24
  • [ 1261739-13-2 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / toluene / 20 h / 130 °C 2: tetrakis(triphenylphosphine) palladium(0); potassium fluoride / acetonitrile / 4 h / 80 °C
  • 25
  • [ 1261739-13-2 ]
  • [ 1859084-08-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / toluene / 20 h / 130 °C 2: tetrakis(triphenylphosphine) palladium(0); potassium fluoride / acetonitrile / 4 h / 80 °C 3: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; 1,4-dioxane / 80 °C
  • 26
  • [ 1261739-13-2 ]
  • [ 1859081-46-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / toluene / 20 h / 130 °C 2: tetrakis(triphenylphosphine) palladium(0); potassium fluoride / acetonitrile / 4 h / 80 °C 3: caesium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; 1,4-dioxane / 80 °C 4: 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine / N,N-dimethyl-formamide / 60 °C
  • 27
  • [ 1261739-13-2 ]
  • [ 1859084-10-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / toluene / 20 h / 130 °C 2: tetrakis(triphenylphosphine) palladium(0); potassium fluoride / acetonitrile / 4 h / 80 °C 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / water; 1,4-dioxane / 110 °C
  • 28
  • [ 1261739-13-2 ]
  • [ 1859084-14-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / toluene / 20 h / 130 °C 2: tetrakis(triphenylphosphine) palladium(0); potassium fluoride / acetonitrile / 4 h / 80 °C 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / water; 1,4-dioxane / 110 °C 4: sodium hydroxide; water / methanol / 4 h / Reflux
  • 29
  • [ 1261739-13-2 ]
  • [ 1859083-42-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / toluene / 20 h / 130 °C 2: tetrakis(triphenylphosphine) palladium(0); potassium fluoride / acetonitrile / 4 h / 80 °C 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / water; 1,4-dioxane / 110 °C 4: sodium hydroxide; water / methanol / 4 h / Reflux 5: triethylamine; HATU / dichloromethane / 20 °C
  • 30
  • [ 1261739-13-2 ]
  • [ 1859084-17-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / toluene / 20 h / 130 °C 2: tetrakis(triphenylphosphine) palladium(0); potassium fluoride / acetonitrile / 4 h / 80 °C 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / toluene; water / 100 °C
  • 31
  • [ 1261739-13-2 ]
  • [ 1842396-20-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / toluene / 20 h / 130 °C 2: tetrakis(triphenylphosphine) palladium(0); potassium fluoride / acetonitrile / 4 h / 80 °C 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / toluene; water / 100 °C 4: sodium hydroxide; water / methanol / 80 °C
  • 32
  • [ 1261739-13-2 ]
  • [ 1859081-55-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / toluene / 20 h / 130 °C 2: tetrakis(triphenylphosphine) palladium(0); potassium fluoride / acetonitrile / 4 h / 80 °C 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / toluene; water / 100 °C 4: sodium hydroxide; water / methanol / 80 °C 5: triethylamine; HATU / dichloromethane / 25 - 40 °C
  • 33
  • [ 1261739-13-2 ]
  • [ 1859084-26-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / toluene / 20 h / 130 °C 2: caesium carbonate; bis(tri-t-butylphosphine)palladium(0) / tetrahydrofuran; water / 40 °C / Inert atmosphere
  • 34
  • [ 1261739-13-2 ]
  • [ 1859084-32-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium acetate; tricyclohexylphosphine; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 5.5 h / 150 °C / Sealed tube 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / water; 1,4-dioxane / 20 h / 80 °C
  • 35
  • [ 1261739-13-2 ]
  • [ 1859084-35-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium acetate; tricyclohexylphosphine; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 5.5 h / 150 °C / Sealed tube 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / water; 1,4-dioxane / 20 h / 80 °C 3: sodium hydroxide; water / methanol / 2 h / 80 °C
  • 36
  • [ 1261739-13-2 ]
  • [ 1859081-61-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: potassium acetate; tricyclohexylphosphine; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 5.5 h / 150 °C / Sealed tube 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / water; 1,4-dioxane / 20 h / 80 °C 3: sodium hydroxide; water / methanol / 2 h / 80 °C 4: triethylamine; HATU / dichloromethane / 2 h / 20 °C 5: ammonium hydroxide / ethanol / Resolution of racemate
  • 37
  • [ 1261739-13-2 ]
  • [ 1859081-64-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium acetate; tricyclohexylphosphine; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 5.5 h / 150 °C / Sealed tube 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / water; 1,4-dioxane / 20 h / 80 °C 3.1: sodium hydroxide; water / methanol / 2 h / 80 °C 4.1: Silicycle SiliaBond® carbonate resin / methanol / 20 °C 4.2: 20 °C
Multi-step reaction with 5 steps 1: potassium acetate; tricyclohexylphosphine; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 5.5 h / 150 °C / Sealed tube 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / water; 1,4-dioxane / 20 h / 80 °C 3: sodium hydroxide; water / methanol / 2 h / 80 °C 4: triethylamine; HATU / dichloromethane / 2 h / 20 °C 5: ammonium hydroxide / ethanol / Resolution of racemate
  • 38
  • [ 1261739-13-2 ]
  • [ 1859081-61-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium acetate; tricyclohexylphosphine; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 5.5 h / 150 °C / Sealed tube 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / water; 1,4-dioxane / 20 h / 80 °C 3: sodium hydroxide; water / methanol / 2 h / 80 °C 4: triethylamine; HATU / dichloromethane / 2 h / 20 °C
  • 39
  • [ 1261739-13-2 ]
  • [ 1859084-48-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / toluene / 20 h / 130 °C 2: sodium hydroxide; water; tetrakis(triphenylphosphine) palladium(0) / acetonitrile / 6 h / 80 °C
  • 40
  • [ 1261739-13-2 ]
  • [ 2769931-56-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 °C / Inert atmosphere 2.1: pyridinium 4-toluenesulfonate; magnesium(II) sulfate / 1,2-dichloro-ethane / 12 h / 80 °C / Inert atmosphere 3.1: diethyl ether; tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C 4.2: 2 h / 0 °C 5.1: anhydrous potassium acetate; chloro(2-dicyclohexylphosphino-2′,4′,6′-tri-i-propyl-1,1′-biphenyl)(2′-amino-1,1′-biphenyl-2-yl) palladium(II) / 1,4-dioxane / 3 h / 90 °C / Inert atmosphere 6.1: anhydrous sodium carbonate; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / lithium hydroxide monohydrate; 1,4-dioxane / 4 h / 65 °C / Inert atmosphere 7.1: acetyl chloride / methanol / 1 h / 25 °C 8.1: triethylamine / dichloromethane / 16 h / 30 °C 9.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C
  • 41
  • [ 1261739-13-2 ]
  • [ 1060801-47-9 ]
YieldReaction ConditionsOperation in experiment
With diisobutylaluminium hydride In dichloromethane; toluene at -78℃; for 1h; Inert atmosphere; 129 Step 1: 4-chloro-5-methylpicolinaldehyde (B30) To a solution of ethyl 4-chloro-5-methylpicolinate (B29, 1.2 g, 6.01 mmol) in anhydrous DCM (20 mL) was added DIBAL-H (9.02 mL,9.02 mmol) (1.0 M in toluene) slowly at -78 °C, and the reaction was stirred at -78 °C under nitrogen for 1 h. LCMS showed the formation of the desired product mass. The reaction was poured into water (50 mL) and extracted with DCM (3 × 20 mL). The combined organic layers were washed with brine (20 mL), dried (Na2SO4), filtered and concentrated to afford 4-chloro-5-methylpicolinaldehyde (B30), which was carried forward without purification. LC-MS: 156.2 (M+1).
With diisobutylaluminium hydride In dichloromethane; toluene at -78℃; for 1h; Inert atmosphere; 129 Step 1: 4-chloro-5-methylpicolinaldehyde (B30) To a solution of ethyl 4-chloro-5-methylpicolinate (B29, 1.2 g, 6.01 mmol) in anhydrous DCM (20 mL) was added DIBAL-H (9.02 mL,9.02 mmol) (1.0 M in toluene) slowly at -78 °C, and the reaction was stirred at -78 °C under nitrogen for 1 h. LCMS showed the formation of the desired product mass. The reaction was poured into water (50 mL) and extracted with DCM (3 × 20 mL). The combined organic layers were washed with brine (20 mL), dried (Na2SO4), filtered and concentrated to afford 4-chloro-5-methylpicolinaldehyde (B30), which was carried forward without purification. LC-MS: 156.2 (M+1).
  • 42
  • [ 1261739-13-2 ]
  • [ 2769929-21-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 °C / Inert atmosphere 2.1: pyridinium 4-toluenesulfonate; magnesium(II) sulfate / 1,2-dichloro-ethane / 12 h / 80 °C / Inert atmosphere 3.1: diethyl ether; tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C 4.2: 2 h / 0 °C
  • 43
  • [ 1261739-13-2 ]
  • [ 2769930-83-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 °C / Inert atmosphere 2.1: pyridinium 4-toluenesulfonate; magnesium(II) sulfate / 1,2-dichloro-ethane / 12 h / 80 °C / Inert atmosphere 3.1: diethyl ether; tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C 4.2: 2 h / 0 °C 5.1: anhydrous potassium acetate; chloro(2-dicyclohexylphosphino-2′,4′,6′-tri-i-propyl-1,1′-biphenyl)(2′-amino-1,1′-biphenyl-2-yl) palladium(II) / 1,4-dioxane / 3 h / 90 °C / Inert atmosphere 6.1: anhydrous sodium carbonate; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / lithium hydroxide monohydrate; 1,4-dioxane / 4 h / 65 °C / Inert atmosphere 7.1: acetyl chloride / methanol / 1 h / 25 °C 8.1: triethylamine / dichloromethane / 16 h / 30 °C
  • 44
  • [ 1261739-13-2 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 °C / Inert atmosphere 2.1: pyridinium 4-toluenesulfonate; magnesium(II) sulfate / 1,2-dichloro-ethane / 12 h / 80 °C / Inert atmosphere 3.1: diethyl ether; tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C 4.2: 2 h / 0 °C 5.1: anhydrous potassium acetate; chloro(2-dicyclohexylphosphino-2′,4′,6′-tri-i-propyl-1,1′-biphenyl)(2′-amino-1,1′-biphenyl-2-yl) palladium(II) / 1,4-dioxane / 3 h / 90 °C / Inert atmosphere
  • 45
  • [ 1261739-13-2 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 °C / Inert atmosphere 2.1: pyridinium 4-toluenesulfonate; magnesium(II) sulfate / 1,2-dichloro-ethane / 12 h / 80 °C / Inert atmosphere 3.1: diethyl ether; tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C 4.2: 2 h / 0 °C 5.1: anhydrous potassium acetate; chloro(2-dicyclohexylphosphino-2′,4′,6′-tri-i-propyl-1,1′-biphenyl)(2′-amino-1,1′-biphenyl-2-yl) palladium(II) / 1,4-dioxane / 3 h / 90 °C / Inert atmosphere 6.1: anhydrous sodium carbonate; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / lithium hydroxide monohydrate; 1,4-dioxane / 4 h / 65 °C / Inert atmosphere
  • 46
  • [ 1261739-13-2 ]
  • [ 2769930-82-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 °C / Inert atmosphere 2.1: pyridinium 4-toluenesulfonate; magnesium(II) sulfate / 1,2-dichloro-ethane / 12 h / 80 °C / Inert atmosphere 3.1: diethyl ether; tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C 4.2: 2 h / 0 °C 5.1: anhydrous potassium acetate; chloro(2-dicyclohexylphosphino-2′,4′,6′-tri-i-propyl-1,1′-biphenyl)(2′-amino-1,1′-biphenyl-2-yl) palladium(II) / 1,4-dioxane / 3 h / 90 °C / Inert atmosphere 6.1: anhydrous sodium carbonate; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / lithium hydroxide monohydrate; 1,4-dioxane / 4 h / 65 °C / Inert atmosphere 7.1: acetyl chloride / methanol / 1 h / 25 °C
  • 47
  • [ 1261739-13-2 ]
  • [ 2769931-57-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 °C / Inert atmosphere 2.1: pyridinium 4-toluenesulfonate; magnesium(II) sulfate / 1,2-dichloro-ethane / 12 h / 80 °C / Inert atmosphere 3.1: diethyl ether; tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C 4.2: 2 h / 0 °C 5.1: anhydrous potassium acetate; chloro(2-dicyclohexylphosphino-2′,4′,6′-tri-i-propyl-1,1′-biphenyl)(2′-amino-1,1′-biphenyl-2-yl) palladium(II) / 1,4-dioxane / 3 h / 90 °C / Inert atmosphere 6.1: anhydrous sodium carbonate; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / lithium hydroxide monohydrate; 1,4-dioxane / 4 h / 65 °C / Inert atmosphere 7.1: acetyl chloride / methanol / 1 h / 25 °C 8.1: triethylamine / dichloromethane / 16 h / 30 °C 9.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C 10.1: trifluoroacetic acid / dichloromethane / 1 h / 25 °C
  • 48
  • [ 1261739-13-2 ]
  • [ 2769936-55-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 11 steps 1.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 °C / Inert atmosphere 2.1: pyridinium 4-toluenesulfonate; magnesium(II) sulfate / 1,2-dichloro-ethane / 12 h / 80 °C / Inert atmosphere 3.1: diethyl ether; tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C 4.2: 2 h / 0 °C 5.1: anhydrous potassium acetate; chloro(2-dicyclohexylphosphino-2′,4′,6′-tri-i-propyl-1,1′-biphenyl)(2′-amino-1,1′-biphenyl-2-yl) palladium(II) / 1,4-dioxane / 3 h / 90 °C / Inert atmosphere 6.1: anhydrous sodium carbonate; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / lithium hydroxide monohydrate; 1,4-dioxane / 4 h / 65 °C / Inert atmosphere 7.1: acetyl chloride / methanol / 1 h / 25 °C 8.1: triethylamine / dichloromethane / 16 h / 30 °C 9.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C 10.1: trifluoroacetic acid / dichloromethane / 1 h / 25 °C 11.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 16 h / 25 °C
  • 49
  • [ 1261739-13-2 ]
  • [ 2769931-91-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 °C / Inert atmosphere 2: pyridinium 4-toluenesulfonate; magnesium(II) sulfate / 1,2-dichloro-ethane / 12 h / 80 °C / Inert atmosphere
  • 50
  • [ 1261739-13-2 ]
  • [ 2769931-92-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 °C / Inert atmosphere 2: pyridinium 4-toluenesulfonate; magnesium(II) sulfate / 1,2-dichloro-ethane / 12 h / 80 °C / Inert atmosphere 3: diethyl ether; tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
Same Skeleton Products
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