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[ CAS No. 113898-56-9 ] {[proInfo.proName]}

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Product Details of [ 113898-56-9 ]

CAS No. :113898-56-9 MDL No. :MFCD14698241
Formula : C8H8FNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :AKVVBYDLMJMJRW-UHFFFAOYSA-N
M.W : 169.15 Pubchem ID :14296371
Synonyms :

Calculated chemistry of [ 113898-56-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 40.28
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) : -6.26 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.84
Log Po/w (XLOGP3) : 1.51
Log Po/w (WLOGP) : 1.82
Log Po/w (MLOGP) : 1.09
Log Po/w (SILICOS-IT) : 1.94
Consensus Log Po/w : 1.64

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.01
Solubility : 1.65 mg/ml ; 0.00973 mol/l
Class : Soluble
Log S (Ali) : -1.94
Solubility : 1.94 mg/ml ; 0.0115 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.78
Solubility : 0.281 mg/ml ; 0.00166 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.71

Safety of [ 113898-56-9 ]

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 [ 113898-56-9 ]

* 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 [ 113898-56-9 ]

[ 113898-56-9 ] Synthesis Path-Downstream   1~17

  • 1
  • [ 116241-52-2 ]
  • [ 113898-56-9 ]
  • [ 116241-59-9 ]
YieldReaction ConditionsOperation in experiment
With triethylamine for 0.0833333h; Ambient temperature; Yield given. Yields of byproduct given;
  • 2
  • [ 614-18-6 ]
  • [ 113898-56-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: NaBF4, 20 percentF2/N2 / acetonitrile / -40 °C 2: Et3N / 0.08 h / Ambient temperature
  • 3
  • [ 861359-74-2 ]
  • [ 113898-56-9 ]
  • [ 679431-51-7 ]
  • (R)-ethyl 2-(3-fluoropyrrolidin-1-yl)nicotinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% In N,N-dimethyl-formamide 1 Step 1: Step 1: (R)-ethyl 2-(3-fluoropyrrolidin-1-yl)nicotinate To a solution of ethyl 2-fluoronicotinate (0.074 g, 0.48 mmol) in DMF (0.3 mL) was added diisopropylethyl amine (0.25 mL, 1.4 mmol), and (R)-3-fluoropyrrolidine (0.090 g, 0.72 mmol). The resulting mixture was irradiated with microwaves (100° C.) for 1 h and loaded directly onto a silica column. Eluting the column with EtOAc/hexanes (0-100%) provided (R)-ethyl 2-(3-fluoropyrrolidin-1-yl)nicotinate as a clear oil (0.100 g, 94% yield); MS (ESI) m/z 239 [M+H]+.
  • 4
  • [ 113898-56-9 ]
  • (R)-3-(chloromethyl)-2-(3-fluoropyrrolidin-1-yl)pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 100 °C / Microwave irradiation 2: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C 3: thionyl chloride / dichloromethane / 1 h / 0 - 20 °C
  • 5
  • [ 113898-56-9 ]
  • 2-[[2-[(3R)-3-fluoropyrrolidin-1-yl]pyridin-3-yl]methoxy]-6-hydroxybenzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 100 °C / Microwave irradiation 2: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C 3: thionyl chloride / dichloromethane / 1 h / 0 - 20 °C 4: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 60 °C
  • 6
  • [ 113898-56-9 ]
  • [ 679431-51-7 ]
  • (R)-ethyl 2-(3-fluoropyrrolidin-1-yl)nicotinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 100℃; for 1h; Microwave irradiation; 1 Step 1: (R)-ethyl 2-(3-fluoropyrrolidin-1-yl)nicotinate Step 1: (R)-ethyl 2-(3-fluoropyrrolidin-1-yl)nicotinate [0229] To a solution of ethyl 2-fluoronicotinate (0.074 g, 0.48 mmol) in DMF (0.3 mL) was added diisopropylethyl amine (0.25 mL, 1.4 mmol), and (R)-3-fluoropyrrolidine (0.090 g, 0.72 mmol). The resulting mixture was irradiated with microwaves (100° C.) for 1 h and loaded directly onto a silica column. Eluting the column with EtOAc/hexanes (0-100%) provided (R)-ethyl 2-(3-fluoropyrrolidin-1-yl)nicotinate as a clear oil (0.100 g, 94% yield); MS (ESI) m/z 239 [M+H]+.
  • 7
  • [ 280-13-7 ]
  • [ 113898-56-9 ]
  • methyl 2-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)nicotinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 100℃; for 1h;Microwave irradiation; Step 1a. To a solution of ethyl 2-fluoronicotinate (0.15 g, 0.97 mmol) in NMP (0.5 mL) was added diisopropylethyl amine (0.50 mL, 2.9 mmol), and 8-oxa-3-azabicyclo[3.2.1]octane (0.17 g, 0.72 mmol). The resulting mixture was irradiated with microwaves (100 C.) for 1 h and loaded directly onto a silica column. Eluting the column with EtOAc/hexanes (0-100%) provided methyl 2-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)nicotinate as a clear oil (0.100 g, 42% yield). MS (ES) for C13H16N2O3: 249 (MH+).
  • 8
  • [ 113898-56-9 ]
  • 2-((2-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyridin-3-yl)methoxy)-6-hydroxybenzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 1 h / 100 °C / Microwave irradiation 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C 2.2: 1 h 3.1: thionyl chloride / dichloromethane / 1 h / 0 - 20 °C 4.1: caesium carbonate / N,N-dimethyl-formamide / 0.5 h / 60 °C 5.1: diisobutylaluminium hydride / dichloromethane / 3 h / -78 - 20 °C
  • 9
  • [ 113898-56-9 ]
  • (2-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyridin-3-yl)methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 1 h / 100 °C / Microwave irradiation 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C 2.2: 1 h
  • 10
  • [ 113898-56-9 ]
  • 3-(3-(chloromethyl)pyridin-2-yl)-8-oxa-3-azabicyclo[3.2.1]octane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 1 h / 100 °C / Microwave irradiation 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C 2.2: 1 h 3.1: thionyl chloride / dichloromethane / 1 h / 0 - 20 °C
  • 11
  • [ 113898-56-9 ]
  • 5-((2-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyridin-3-yl)methoxy)-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 1 h / 100 °C / Microwave irradiation 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C 2.2: 1 h 3.1: thionyl chloride / dichloromethane / 1 h / 0 - 20 °C 4.1: caesium carbonate / N,N-dimethyl-formamide / 0.5 h / 60 °C
  • 12
  • (1R,5S)-8-oxa-3-azabicyclo[3.2.1]octane [ No CAS ]
  • [ 113898-56-9 ]
  • methyl 2-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)nicotinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 100℃; for 1h; Microwave irradiation; 5.1a Step 1a. Step 1a.To a solution of ethyl 2-fluoronicotinate (0.15 g, 0.97 mmol) in NMP (0.5 mL) was added diisopropylethyl amine (0.50 mL, 2.9 mmol), and 8-oxa-3-azabicyclo[3.2.1]octane (0.17 g, 0.72 mmol). The resulting mixture was irradiated with microwaves (100° C.) for 1 h and loaded directly onto a silica column. Eluting the column with EtOAc/hexanes (0-100%) provided methyl 2-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)nicotinate as a clear oil (0.100 g, 42% yield). MS (ES) for C13H16N2O3: 249 (MH+).
  • 13
  • [ 105-56-6 ]
  • [ 927-63-9 ]
  • [ 113898-56-9 ]
YieldReaction ConditionsOperation in experiment
90.4% In a reactor, 59 mL (0.5 mol) of cyanoacetic acid ethyl ester was added,1-butyl-3-methylImidazole trifluoroAcetate50 mL,3-dimethylaminopropenal 62 mL (0.5 mol) was homogeneously mixed,Electric furnace sets heated to 120 temperature and heat 2h reaction,TLC detection (petroleum ether: methylene chloride 1: 2 expansion, sublimation iodine color) 3-dimethylaminopropenal reaction completely, cooled to room temperature, organic solvent extraction of 60mL of toluene 3 times,The residual phase was washed with water and dried in vacuo. The organic phase was passed through a dry HF gas and the reaction was followed by HPLC until the reaction was complete. Add the mass fraction of 20% potassium carbonate solution to adjust the pH = 5-6, liquid, water layerWith toluene 20mL × 3 times extraction,The organic layers were combined, washed with water, separated by molecular sieves, filtered, and the solvent was distilled off under reduced pressure.The yield of ethyl 2-fluoronicotinate and 76.5 g of light brown liquid was 90.4%.
  • 14
  • [ 105-56-6 ]
  • [ 113898-56-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: copper(II) oxide; dodecyltrimethylammonium bromide / water / 30 h / 110 °C / 1875.19 Torr / High pressure; Inert atmosphere; Green chemistry; Industrial scale 2: hydrogen fluoride / Green chemistry; Industrial scale
Multi-step reaction with 2 steps 1: pyridine / 40 °C / Microwave irradiation 2: hydrogen fluoride / 0.17 h / 0 °C / Microwave irradiation
  • 15
  • C16H26N2O2 [ No CAS ]
  • [ 113898-56-9 ]
YieldReaction ConditionsOperation in experiment
With hydrogen fluoride Green chemistry; Industrial scale; 6 Example 6 (Synthesis of 2-fluoro-niacin) 69 mL (0.5 mol) of N, N-dibutylaminopropenal,8.5 g of HCO (CO) 4, 12.5 g of trimethyl dodecylammonium bromide and 50 mL of deionized water were added to the hydrothermal reactor, and 65 mL (0.6 mol) of ethyl cyanoacetate was added and mixed at 106 ° C , Nitrogen 0.6MPa under hydrothermal reaction 0.4h, after the end of the reaction filter, methyl tert-butyl ether 140g extraction, the organic phase and then into the dry HF gas reaction, TLC (ethyl acetate expansion,Under the UV lamp to observe the reaction until the end of the reaction, the reaction solution by adding 30% mass of ammonium bicarbonate solution to adjust the pH to neutral, separated organic phase, vacuum distillation solvent (recovery apply)The residue was distilled under reduced pressure and the 110-115 ° C / 1 mmHg fraction was collected to give ethyl 2-fluoro nicotinate as a pale brown liquid, ethyl 2-fluoronicotinate was 99.0% and the yield was 95.0%.
  • 16
  • C12H18N2O2 [ No CAS ]
  • [ 113898-56-9 ]
YieldReaction ConditionsOperation in experiment
89.7% With hydrogen fluoride at 0℃; for 0.166667h; Microwave irradiation; 6 Example 6 Synthesis of ethyl 2-fluoronicotinate In a 500 mL three-necked flask equipped with a thermometer,First add 3-diethylamino acrolein61mL (0.5mol) and twoEthylamine (20 mL), ethyl cyanoacetate (65 mL, 0.6 mol) was added, and the prepared device was placed in a microwave apparatus. Set up the microwavesRadioactive conditions, reaction at a temperature of 0°C, microwave power of 50 W, and a frequency of 915 MHz, TLC detection (petroleum ether: dichloromethane 1:2 development, sublimation iodine development) 3-diethylaminoacrolein reaction is complete .After that, HF gas is introduced again and the microwave radiation condition is 0°C.The reaction is about 10 minutes under the conditions of microwave power of 20W and frequency of 16KHz.HPLC followed the reaction until the reaction was over. Then after the reaction is over,Aqueous ammonia solution was added to adjust pH=5-6 to separate the liquid.The aqueous layer was extracted with ethyl acetate (20 mL × 3 times) and the organic layers were combined.The molecular sieve was dried overnight, filtered, and the solvent was removed under reduced pressure to prepare 2-fluoronicotinic acid ethyl ester.Light brown liquid 75.9 g, yield 89.7%.
  • 17
  • [ 105-56-6 ]
  • [ 13070-22-9 ]
  • [ 113898-56-9 ]
YieldReaction ConditionsOperation in experiment
85.2% Stage #1: ethyl 2-cyanoacetate; 3-(N,N-diethylamino)propenal With diethylamine at 0℃; Sonication; Stage #2: With hydrogen fluoride at 0℃; for 0.166667h; Sonication; 6 Example 6 Synthesis of 2-Fluoronicotinic Acid Ethyl Ester In a 500 mL three-necked flask equipped with a thermometer, First add 3-diethylaminoacrolein 61 mL (0.5 mol) And diethylamine 20mL, After adding ethyl cyanoacetate 65 mL (0.6 mol), Place the prepared device in the sonicator. Set ultrasonic radiation conditions At a temperature of 0 °C, Ultrasonic power is 50W Reacts with a frequency of 16 ΚΗz, TLC test (petroleum ether: dichloromethane 1:2 development, sublimation iodine color development) The reaction of 3-diethylaminopropenal is complete. After that, HF gas is added again. Ultrasonic radiation conditions are 0 °C Ultrasonic power is 20W React with the frequency of 16ΚΗz for about 10 minutes, HPLC followed the reaction until the reaction was over. Then after the reaction is over, Add ammonia solution to adjust pΗ=5-6, Liquid separation, The aqueous layer was extracted with ethyl acetate 20 mLX 3 times. Combine organic layers, The sieve was dried overnight, filter, Remove the solvent under reduced pressure Preparation of ethyl 2-fluoro nicotinate, Light brown liquid 72.1g, the yield was 85.2%.
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