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[ CAS No. 1256358-90-3 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 1256358-90-3
Chemical Structure| 1256358-90-3
Structure of 1256358-90-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1256358-90-3 ]

CAS No. :1256358-90-3 MDL No. :MFCD23140955
Formula : C11H16BNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :UQTTXNHBLCIRLA-UHFFFAOYSA-N
M.W : 221.06 Pubchem ID :45786003
Synonyms :

Calculated chemistry of [ 1256358-90-3 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.55
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 63.54
TPSA : 51.32 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.12 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.74
Log Po/w (WLOGP) : 0.67
Log Po/w (MLOGP) : 0.45
Log Po/w (SILICOS-IT) : 1.45
Consensus Log Po/w : 0.66

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.89
Solubility : 2.86 mg/ml ; 0.0129 mol/l
Class : Very soluble
Log S (Ali) : -1.4
Solubility : 8.87 mg/ml ; 0.0401 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.54
Solubility : 0.0639 mg/ml ; 0.000289 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.77

Safety of [ 1256358-90-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1256358-90-3 ]

* 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 [ 1256358-90-3 ]

[ 1256358-90-3 ] Synthesis Path-Downstream   1~44

  • 2
  • [ 1244041-71-1 ]
  • 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one [ No CAS ]
  • C17H17N3O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With Pd-118 In water; acetonitrile at 80 - 100℃; Microwave irradiation;
  • 3
  • [ 36953-37-4 ]
  • [ 73183-34-3 ]
  • 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tris-(dibenzylideneacetone)dipalladium(0); potassium acetate; tricyclohexylphosphine; In 1,4-dioxane; at 85℃; for 3h;Inert atmosphere; (0692) 4-Bromopyridin-2-(1H)-one (1.0 g, 5.7 mmol), bis(pinacolato)diboron (1.6 g, 6.3 mmol) and potassium acetate (0.84 g, 8.55 mmol) were added to 1,4-dioxane (20 mL). Under the protection of nitrogen gas, tricyclohexyl phosphine (193 mg) and tris(dibenzylideneacetone)dipalladium (300 mg) were added. The mixture was heated to 85 C. and reacted for 3 h, then cooled to room temperature, and filtrated under suction. The filtrate was concentrated, and then directly used in the next step.
  • 4
  • [ 1256358-90-3 ]
  • [ 1820585-31-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / water; 1,4-dioxane / 12 h / 90 °C / Inert atmosphere 2: hydrogen; platinum(IV) oxide / methanol / 20 °C
  • 5
  • [ 1256358-90-3 ]
  • [ 1820584-55-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / water; 1,4-dioxane / 12 h / 90 °C / Inert atmosphere 2: hydrogen; platinum(IV) oxide / methanol / 20 °C 3: trifluoroacetic acid / 1,4-dioxane / 50 °C / Inert atmosphere
  • 6
  • [ 1256358-90-3 ]
  • [ 59557-91-4 ]
  • [ 1820585-30-5 ]
YieldReaction ConditionsOperation in experiment
600 mg With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 90℃; for 12h; Inert atmosphere; 21.2 (2) Preparation of 4-(4-amino-3-methoxyphenyl)pyridin-2(1H)-one (0694) 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one (1.27 g, 5.7 mmol), 4-bromo-2-methoxyaniline (1.16 g, 5.7 mmol) and potassium carbonate (1.97 g, 14.3 mmol) were added to 1,4-dioxane (50 mL) and water (10 mL). Under the protection of nitrogen gas, [1,1′-bis(diphenyphosphino)ferrocene]dichloropalladium ( II) (417 mg) was added. The mixture was heated to 90° C. and reacted for 12 h, and then filtrated under suction. The filtrate was concentrated, and the crude product was purified by silica gel column chromatography (dichloromethane:methanol=50:1) to get the title compound (600 mg, yield: 48.8%).
  • 7
  • [ 1256358-90-3 ]
  • [ 2098332-94-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: caesium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 2: sodium carbonate; bis-triphenylphosphine-palladium(II) chloride / acetonitrile; water / 1 h / 70 °C / Inert atmosphere
  • 8
  • [ 1256358-90-3 ]
  • [ 2098331-99-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: caesium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 2: sodium carbonate; bis-triphenylphosphine-palladium(II) chloride / acetonitrile; water / 1 h / 70 °C / Inert atmosphere 3: sodium carbonate / acetonitrile; water / 0.25 h / 150 °C / Microwave irradiation; Sealed tube
  • 9
  • [ 1256358-90-3 ]
  • [ 2098332-00-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: caesium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 2: sodium carbonate; bis-triphenylphosphine-palladium(II) chloride / acetonitrile; water / 1 h / 70 °C / Inert atmosphere 3: hydrogenchloride / tetrahydrofuran; water / 48 h 4: sodium carbonate / acetonitrile; water / 0.25 h / 150 °C / Microwave irradiation
  • 10
  • [ 1256358-90-3 ]
  • [ 2098332-95-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: caesium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 2: sodium carbonate; bis-triphenylphosphine-palladium(II) chloride / acetonitrile; water / 1 h / 70 °C / Inert atmosphere 3: hydrogenchloride / tetrahydrofuran; water / 48 h
  • 11
  • [ 1256358-90-3 ]
  • [ 2098332-01-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: caesium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 2: sodium carbonate; bis-triphenylphosphine-palladium(II) chloride / acetonitrile; water / 1 h / 70 °C / Inert atmosphere 3: hydrogenchloride / tetrahydrofuran; water / 48 h 4: sodium cyanoborohydride; ethanol / 20 °C 5: sodium carbonate / acetonitrile; water / 0.25 h / 150 °C / Microwave irradiation
  • 12
  • [ 1256358-90-3 ]
  • [ 2098332-02-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: caesium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 2: sodium carbonate; bis-triphenylphosphine-palladium(II) chloride / acetonitrile; water / 1 h / 70 °C / Inert atmosphere 3: hydrogenchloride / tetrahydrofuran; water / 48 h 4: sodium cyanoborohydride; acetic acid; methanol / 20 °C 5: sodium carbonate / acetonitrile; water / 0.25 h / 150 °C / Microwave irradiation
  • 13
  • [ 1256358-90-3 ]
  • [ 2098333-11-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: caesium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 2: sodium carbonate; bis-triphenylphosphine-palladium(II) chloride / acetonitrile; water / 1 h / 70 °C / Inert atmosphere
  • 14
  • [ 1256358-90-3 ]
  • [ 2098332-08-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: caesium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 2: sodium carbonate; bis-triphenylphosphine-palladium(II) chloride / acetonitrile; water / 1 h / 70 °C / Inert atmosphere 3: sodium carbonate / acetonitrile; water / 0.25 h / 150 °C / Microwave irradiation; Sealed tube
  • 15
  • [ 1256358-90-3 ]
  • [ 2098333-12-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: caesium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 2: sodium carbonate; bis-triphenylphosphine-palladium(II) chloride / acetonitrile; water / 1 h / 70 °C / Inert atmosphere 3: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
  • 16
  • [ 1256358-90-3 ]
  • [ 2098332-09-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: caesium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 2: sodium carbonate; bis-triphenylphosphine-palladium(II) chloride / acetonitrile; water / 1 h / 70 °C / Inert atmosphere 3: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 4: sodium carbonate / acetonitrile; water / 0.25 h / 150 °C / Microwave irradiation; Sealed tube
  • 17
  • [ 1256358-90-3 ]
  • [ 2098332-10-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: caesium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 2: sodium carbonate; bis-triphenylphosphine-palladium(II) chloride / acetonitrile; water / 1 h / 70 °C / Inert atmosphere 3: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 4: sodium carbonate / acetonitrile; water / 0.25 h / 150 °C / Microwave irradiation; Sealed tube 5: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere
  • 18
  • [ 1256358-90-3 ]
  • [ 2098332-11-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: caesium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 2: sodium carbonate; bis-triphenylphosphine-palladium(II) chloride / acetonitrile; water / 1 h / 70 °C / Inert atmosphere 3: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 4: sodium carbonate / acetonitrile; water / 0.25 h / 150 °C / Microwave irradiation; Sealed tube 5: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 20 °C
  • 19
  • [ 1256358-90-3 ]
  • [ 2098332-83-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: caesium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 2: sodium carbonate; bis-triphenylphosphine-palladium(II) chloride / acetonitrile; water / 1.5 h / 70 °C / Inert atmosphere
  • 20
  • [ 1256358-90-3 ]
  • [ 2098331-88-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: caesium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 2: sodium carbonate; bis-triphenylphosphine-palladium(II) chloride / acetonitrile; water / 1.5 h / 70 °C / Inert atmosphere 3: sodium carbonate; bis-triphenylphosphine-palladium(II) chloride / acetonitrile; water / 1 h / 150 °C / Inert atmosphere; Microwave irradiation
  • 21
  • [ 1256358-90-3 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: caesium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 2: sodium carbonate; bis-triphenylphosphine-palladium(II) chloride / acetonitrile; water / 1 h / 70 °C / Inert atmosphere 3: hydrogenchloride / tetrahydrofuran; water / 48 h 4: sodium cyanoborohydride; ethanol / 20 °C
  • 22
  • [ 1256358-90-3 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: caesium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 2: sodium carbonate; bis-triphenylphosphine-palladium(II) chloride / acetonitrile; water / 1 h / 70 °C / Inert atmosphere 3: hydrogenchloride / tetrahydrofuran; water / 48 h 4: sodium cyanoborohydride; acetic acid; methanol / 20 °C
  • 23
  • [ 1256358-90-3 ]
  • [ 2098331-94-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: caesium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 2: sodium carbonate; bis-triphenylphosphine-palladium(II) chloride / acetonitrile; water / 1.5 h / 70 °C / Inert atmosphere 3: sodium carbonate; bis-triphenylphosphine-palladium(II) chloride / acetonitrile; water / 1 h / 150 °C / Inert atmosphere; Microwave irradiation
  • 24
  • [ 1256358-90-3 ]
  • [ 2098331-96-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: caesium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 2: sodium carbonate; bis-triphenylphosphine-palladium(II) chloride / acetonitrile; water / 1.25 h / 70 - 150 °C / Inert atmosphere; Microwave irradiation; Sealed tube
  • 25
  • [ 1256358-90-3 ]
  • [ 100-39-0 ]
  • [ 2098333-13-0 ]
YieldReaction ConditionsOperation in experiment
65% With caesium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere; 25.1 Step 1:
1-Benzyl-2-oxo-1,2-dihydropyridin-4-ylboronic acid To a solution of 30 mg (0.14 mmol) of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyridin-2-one and 66 mg (0.20 mmol) of cesium carbonate in 1 ml of anhydrous DMF, are added 18 μl (0.15 mmol) of benzyl bromide at ambient temperature. The reaction is stirred overnight under argon. Reaction mixture is then diluted with ethyl acetate, and the precipitate is filtered and rinsed with a small amount of ethyl acetate. The filtrate is concentrated under vacuum and directly purified by flash chromatography with a 30 g C18 column and a water/acetonitrile mixture as eluent. 20 mg of the title compound are obtained. Yield: 65%. MH+: 230.1.
  • 26
  • [ 1256358-90-3 ]
  • [ 766-80-3 ]
  • [ 2098332-81-9 ]
YieldReaction ConditionsOperation in experiment
45% With caesium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere; 1.3 Step 3:1-(3-Chlorobenzyl)-2-oxo-1,2-dihydropyridine-4-boronic acid To a solution of 200 mg (0.91mmol) of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyridin-2-one, 442 mg (1.36 mmol) of cesium carbonate in 1 ml of anhydrous DMF, is added 0.13 ml (1.00 mmol) of 3-chlorobenzyl bromide at ambient temperature. The reaction is stirred overnight under argon. Reaction mixture is then diluted with ethyl acetate, and the precipitate is filtered and rinsed with a small amount of ethyl acetate. The filtrate is concentrated under vacuum and directly purified by flash chromatography with a 30 g C18 column and a water/acetonitrile mixture as eluent. 109 mg of the title compound are obtained. Yield: 45%. MH+: 264.0; 266.0.
  • 27
  • [ 1256358-90-3 ]
  • [ 4916-55-6 ]
  • [ 2098333-30-1 ]
YieldReaction ConditionsOperation in experiment
21% With caesium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere; 39.1 Step 1:
1-Benzyl-2-oxo-1,2-dihydropyridin-4-ylboronic acid General procedure: To a solution of 30 mg (0.14 mmol) of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyridin-2-one and 66 mg (0.20 mmol) of cesium carbonate in 1 ml of anhydrous DMF, are added 18 μl (0.15 mmol) of benzyl bromide at ambient temperature. The reaction is stirred overnight under argon. Reaction mixture is then diluted with ethyl acetate, and the precipitate is filtered and rinsed with a small amount of ethyl acetate. The filtrate is concentrated under vacuum and directly purified by flash chromatography with a 30 g C18 column and a water/acetonitrile mixture as eluent. 20 mg of the title compound are obtained. Yield: 65%. The compound is obtained by the procedure described in example 25 step 1, using 50 mg (0.23 mmol) of4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyridin-2-one, 184 mg (0.57 mmol) of cesium carbonate and 65 mg(0.25 mmol) of 3-(bromomethyl)pyridine hydrobromide instead of benzyl bromide. 11 mg of the title compound areobtained. Yield: 21%. MH+: 231.1.
  • 28
  • [ 70258-18-3 ]
  • [ 1256358-90-3 ]
  • [ 2098333-31-2 ]
YieldReaction ConditionsOperation in experiment
27% With caesium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere; 40.1 Step 1:
1-Benzyl-2-oxo-1,2-dihydropyridin-4-ylboronic acid General procedure: To a solution of 30 mg (0.14 mmol) of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyridin-2-one and 66 mg (0.20 mmol) of cesium carbonate in 1 ml of anhydrous DMF, are added 18 μl (0.15 mmol) of benzyl bromide at ambient temperature. The reaction is stirred overnight under argon. Reaction mixture is then diluted with ethyl acetate, and the precipitate is filtered and rinsed with a small amount of ethyl acetate. The filtrate is concentrated under vacuum and directly purified by flash chromatography with a 30 g C18 column and a water/acetonitrile mixture as eluent. 20 mg of the title compound are obtained. Yield: 65%. The compound is obtained by the procedure described in example 25 step 1, using 50 mg (0.23 mmol) of4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyridin-2-one, 110 mg (0.34 mmol) of cesium carbonate and 40 mg(0.25 mmol) of 2-chloro-5-chloromethylpyridine instead of benzyl bromide. 16 mg of the title compound are obtained. Yield: 27%. MH+: 265.1; 267.1.
  • 29
  • [ 20697-04-5 ]
  • [ 1256358-90-3 ]
  • [ 2098333-37-8 ]
YieldReaction ConditionsOperation in experiment
45% With caesium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere; 44.1 Step 1:
1-Benzyl-2-oxo-1,2-dihydropyridin-4-ylboronic acid General procedure: To a solution of 30 mg (0.14 mmol) of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyridin-2-one and 66 mg (0.20 mmol) of cesium carbonate in 1 ml of anhydrous DMF, are added 18 μl (0.15 mmol) of benzyl bromide at ambient temperature. The reaction is stirred overnight under argon. Reaction mixture is then diluted with ethyl acetate, and the precipitate is filtered and rinsed with a small amount of ethyl acetate. The filtrate is concentrated under vacuum and directly purified by flash chromatography with a 30 g C18 column and a water/acetonitrile mixture as eluent. 20 mg of the title compound are obtained. Yield: 65%. The compound is obtained by the procedure described in example 25 step 1, using 50 mg (0.23 mmol) of4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyridin-2-one, 110 mg (0.34 mmol) of cesium carbonate and 38 mg(0.25 mmol) of 2-(3-chlorophenyl)-oxirane instead of benzyl bromide. 30 mg of the title compound are obtained. Yield: 45%. MH+: 294.1; 296.0.
  • 31
  • [ 1256358-90-3 ]
  • [ 2411962-28-0 ]
  • [ 2411962-37-1 ]
YieldReaction ConditionsOperation in experiment
41% With tetrakis(triphenylphosphine) palladium(0); potassium pivalate In 1,4-dioxane; water at 100℃; 10 Example 10N- (2- (3-hydroxy-3-methylbutyl) -6- (2-oxo-1,2-dihydropyridin-4-yl) -2H-indazol-5-yl) -6 -(trifluoromethyl) pyridine-2-carboxamide Add 1f (70mg, 0.15mmol), 10a (99mg, 0.45mmol), potassium pivalate (105mg, 0.74mmol), tetratriphenylphosphine palladium (88mg, 0.07mmol), dioxane / water into the reaction flask. (25mL, volume ratio 3: 1) as solvent, react at 100 ° C, TLC detected that the reaction of the raw materials was complete, cooled to room temperature, added 20mL of saturated brine, extracted twice with ethyl acetate (30mL × 2), and the organic phase was dried with anhydrous It was dried over sodium sulfate, filtered, concentrated under reduced pressure, and subjected to silica gel column chromatography, eluting with methanol / dichloromethane to obtain compound 10 (30 mg, 41%).
  • 32
  • [ 1256358-90-3 ]
  • [ 2332809-11-5 ]
  • [ 2546208-42-6 ]
YieldReaction ConditionsOperation in experiment
99% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 70℃; for 16h; Inert atmosphere; 45.1 Step 1: A mixture of a (50.0 mg, 0.11 mmol, 1.0 eq), b (76.0 mg, 0.33 mmol, 3.0 eq) in Pd(dppf)Cl2 (8.0 mg, 0.011 mmol, 0.1 eq) and K2CO3 (46.0 mg, 0.33 mmol, 3.0 eq) in dioxane/H2O (3 mL/ 0.5 mL) was stirred at 70 oC under N2 atmosphere for 16 hours. The reaction mixture was filtered with celite and silica gel, and the filter cake was washed with EtOAc (15 mL). The filtrate was concentrated and the residue purified by Prep-TLC (EtOAc) to give c (80.0 mg, >99%) as a yellow solid. LCMS: 452.3 [M+H]+.
  • 33
  • [ 1256358-90-3 ]
  • [ 2068064-97-9 ]
  • [ 2664046-36-8 ]
YieldReaction ConditionsOperation in experiment
50 mg With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane at 60℃; Inert atmosphere; 5 Synthesis of intermediate C5-3: Add C5-2 (0.4mmol, 88mg), C1-7 (0.2mmol, 75mg), K2CO3 (0.3mmol, 42mg), Pd(dppf)Cl2 (0.034mmol, 25mg) and dioxane into a 50mL single-mouth bottle in sequence (5mL), after the reaction was replaced with argon, the reaction was carried out overnight at 60°C under the protection of argon. Cooled to room temperature, the mother liquor was filtered, the filtrate was concentrated, water and ethyl acetate were added, the aqueous phase was extracted with ethyl acetate, the organic phases were combined, the organic phases were washed with saturated brine, dried and concentrated, and subjected to silica gel column chromatography (DCM/MeOH=50 1) Obtain 50 mg of compound C5-3.
  • 34
  • [ 1256358-90-3 ]
  • [ 2664046-41-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane / 60 °C / Inert atmosphere 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / N,N-dimethyl-formamide / 90 °C / Inert atmosphere
  • 35
  • [ 1256358-90-3 ]
  • [ 2664046-80-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane / 60 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 16 h / 80 °C / Inert atmosphere
  • 36
  • [ 1256358-90-3 ]
  • [ 2664046-89-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane / 60 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 80 °C
  • 37
  • [ 1256358-90-3 ]
  • [ 2664046-96-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane / 60 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 80 °C 3: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C
  • 38
  • [ 1256358-90-3 ]
  • [ 2664047-05-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane / 60 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 80 °C 3: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C 4: triethylamine / N,N-dimethyl-formamide / 20 °C
  • 39
  • [ 1256358-90-3 ]
  • [ 2688801-84-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 1.5 h / 80 °C / Inert atmosphere 2: caesium carbonate / N,N-dimethyl-formamide / 0.5 h / 70 °C / Inert atmosphere
  • 40
  • [ 1256358-90-3 ]
  • [ 2688800-62-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 1.5 h / 80 °C / Inert atmosphere 2: caesium carbonate / N,N-dimethyl-formamide / 0.5 h / 70 °C / Inert atmosphere 3: lithium hydroxide; water / tetrahydrofuran; methanol / 2 h / 25 °C
  • 41
  • [ 1256358-90-3 ]
  • [ 2688801-90-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / 1,4-dioxane; water / 12 h / 85 °C / Inert atmosphere 2: potassium carbonate / acetonitrile / 12 h / 50 °C
  • 42
  • [ 1256358-90-3 ]
  • [ 1121604-61-2 ]
  • [ 2688801-92-3 ]
YieldReaction ConditionsOperation in experiment
62.8% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane; water at 80℃; for 12h; Inert atmosphere; 7W.B Step B: Preparation of 4- [6- [ (4-chloro-2-fluoro-phenyl) methoxy] -2-pyridyl] -1H-pyridin-2-one A mixture of 1- [ (3-bromophenoxy) methyl] -4-chloro-2-fluoro-benzene (200 mg, 633.78 umol) , 4- (4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) -1H-pyridin-2-one (168.13 mg, 760.54 umol) , KOAc (186.60 mg, 1.90 mmol) , Pd (dppf) Cl2(9.27 mg, 12.68 umol) in H2O (0.5 mL) and dioxane (2.5 mL) was degassed and purged with N2for 3 times, and then the mixture was stirred at 80 for 12 hr under N2atmosphere. The reaction mixture was filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (SiO2, DCM: MeOH = 0%to 10%) . 4- [3- [ (4-chloro-2-fluoro-phenyl) methoxy] phenyl] -1H-pyridin-2-one (132.5 mg, 62.8%yield) was obtained as a yellow solid. LCMS: m/z330.0 [M+H]+.
  • 43
  • [ 1256358-90-3 ]
  • [ 2428643-63-2 ]
  • [ 2688801-89-8 ]
YieldReaction ConditionsOperation in experiment
82.8% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 85℃; for 12h; Inert atmosphere; 4W.B Step B: Preparation of 3-fluoro-4- ( ( (2'-oxo-1', 2'-dihydro- [2, 4'-bipyridin] -6-yl) oxy)methyl) benzonitrile To a solution of 4- [ (6-bromo-2-pyridyl) oxymethyl] -3-fluoro-benzonitrile (150 mg, 488.41 umol) in dioxane (1.5 mL) and H2O (0.5 mL) was added 4- (4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) -1H-pyridin-2-one (162 mg, 732.62 umol) , Na2CO3(155 mg, 1.47 mmol) and Pd (dppf) Cl2(36 mg, 48.84 umol) . The mixture was stirred at 85 for 12 h under N2. The reaction mixture was quenched with H2O (30 mL) and extracted with EtOAc (30 mL x 3) . The organic layer was washed with brine (50 mL) , dried over Na2SO4, filtered and concentrated. The residue was purified by column (SiO2, DCM: MeOH = 20: 1) . 3-fluoro-4- ( ( (2'-oxo-1', 2'-dihydro- [2, 4'-bipyridin] -6-yl) oxy) methyl) benzonitrile (130 mg, yield: 82.8%) was obtained as yellow solid. LCMS: m/z321.9 [M+H]+.
  • 44
  • [ 1256358-90-3 ]
  • [ 2505461-94-7 ]
  • [ 2649365-31-9 ]
YieldReaction ConditionsOperation in experiment
316.5 mg With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 80℃; for 1.5h; Inert atmosphere; 1W.C Step C: Preparation of 6- ( (4-chloro-2-fluorobenzyl) oxy) - [2, 4'-bipyridin] -2' (1'H) -one To a solution of 2-bromo-6- ( (4-chloro-2-fluorobenzyl) oxy) pyridine (350 mg, 1.11 mmol) in dioxane (2 mL) was added 4- (4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) pyridin-2 (1H) -one (508.44 mg, 2.30 mmol) , Pd (dppf) Cl2(80.90 mg, 110.57 umol) , K2CO3(458.43 mg, 3.32 mmol) and H2O (2 mL) . The suspension was stirred at 80 for 1.5 hr under N2. The dark mixture was diluted with water (5 mL) and extracted with ethyl acetate (5 mL) twice. The organic layer was dried with Na2SO4and filtered. The filtrate was concentrated to give crude (863 mg) as a dark gum. The crude was purified by Combi-flash (silica gel, ethyl acetate in petrol ether from 50100%) to give 6- ( (4-chloro-2-fluorobenzyl) oxy) - [2, 4'-bipyridin] -2' (1'H) -one (316.5 mg, 86.5%yield) as a yellow solid. (The yield was for two steps. ) 1H NMR (400 MHz, DMSO-d6) δ ppm 11.66 (br s, 1 H) 7.85 (t, J=7.44 Hz, 1 H) 7.64 (d, J=7.15 Hz, 1 H) 7.60 (t, J=7.96 Hz, 1 H) 7.42 -7.55 (m, 2 H) 7.32 (dd, J=8.19, 1.71 Hz, 1 H) 7.02 (s, 1 H) 6.96 (d, J=8.38 Hz, 1 H) 6.84 (d, J=6.72 Hz, 1 H) 5.49 (s, 2 H) ; LCMS: m/z 330.9 [M+H]+.
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