124236-37-9|Methyl 5-(trifluoromethyl)picolinate| Ambeed

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Quality Control of [ 124236-37-9 ] Purity: 95% SDS Specification

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Product Details of [ 124236-37-9 ]

CAS No. :	124236-37-9
Formula :	C₈H₆F₃NO₂
M.W :	205.13
SMILES Code :	O=C(OC)C1=NC=C(C(F)(F)F)C=C1
MDL No. :	MFCD08741523
InChI Key :	CHRQADSGOKVKER-UHFFFAOYSA-N
Pubchem ID :	18996919

Safety of [ 124236-37-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H319
Precautionary Statements:	P305+P351+P338

Computational Chemistry of [ 124236-37-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	6
Fraction Csp3	0.25
Num. rotatable bonds	3
Num. H-bond acceptors	6.0
Num. H-bond donors	0.0
Molar Refractivity	40.52
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	39.19 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.81
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.37
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.04
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	1.4
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.24
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.17

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.72
Solubility	0.387 mg/ml ; 0.00189 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.83
Solubility	0.301 mg/ml ; 0.00147 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-2.99
Solubility	0.208 mg/ml ; 0.00101 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.87 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.85

Application In Synthesis of [ 124236-37-9 ]

* 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.

Upstream synthesis route of [ 124236-37-9 ]
Downstream synthetic route of [ 124236-37-9 ]

[ 124236-37-9 ] Synthesis Path-Upstream 1~1

1
[ 124236-37-9 ]
[ 31181-84-7 ]

Yield	Reaction Conditions	Operation in experiment
93%	at 0 - 20℃;	IV. (5-trifluoromethyl-2-pyridinyl)methanol To a solution of methyl 5-trifluoromethyl-pyridine-2-carboxylate (2 g, 9.75 mmol) in MeOH (30 mL) at 0°C was added NaB (738 mg, 19.5 mmol) portionwise. The mixture was stirred at room temperature for 2 h and concentrated. The residue was diluted with water (30 mL), acidified to pH~5 (IN HC1), extracted with EA (3 X 50 mL), dried, concentrated and purified by column chromatography on silica gel to give the title compound as a colorless oil (1.6 g, 93percent yield): 1H NMR (400 MHz, CDC1₃) δ ppm 8.82 (s, 1H), 7.90-7.92 (m, 1H), 7.40-7.42 (m, 1H), 4.82-4.83 (m, 2H), 3.44-3.46 (m, 1H); ES-LCMS m/z 178 ( +H)⁺.
82.2%	at 0 - 20℃; for 1 h;	Compound SM (1.0 g, 4.87 mmol) was dissolved in MeOH (15 mL). At 0 ° C, NaBH4 (368.9 mg, 9.75 mmol) was added portionwise with stirring. Reaction at room temperature for 1 hour. TLC showed the reaction was completed. The pH was adjusted to 5-6 with 1 M HCl solution and the EA extracted (20 mL x 3). The combined organic phases were dried over anhydrous sodium sulfate, filtered and concentrated to give the title compound (710.0 mg, 82.2percent).
72%	Stage #1: With sodium tetrahydroborate In ethanolHeating / reflux Stage #2: With water; ammonium chloride In ethanol at 20℃;	NaBH₄ (0.369 g, 9.75 mmol) was added to Example 34A (1 g, 5 mmol) in EtOH (40 mL). The suspension was heated at reflux overnight. The reaction was cooled to ambient temperature and quenched with saturated NH₄Cl solution. The mixture was diluted with water and extracted with EtOAc. The separated organic layer was washed with water and brine, dried (Na₂SO₄), filtered, and concentrated in vacuo. The crude product was chromatographed on silica gel (Analogix.(R). 25*40 column, 30percent-50percent EtOAc/hexanes eluant) to afford 0.62 g (72percent) of the title compound as a colorless oil. ¹H NMR (300 MHz, CDCl₃) δ 8.84 (s, 1H), 7.94 (dd, J=8.3, 2.1 1H), 7.43 (dd, J=8.2, 0.6 1H), 4.85 (d, J=5.2, 2H), 3.46 (t, J=5.3, 1H).

References: [1] Patent: WO2013/166621, 2013, A1, . Location in patent: Page/Page column 48.
[2] Patent: CN106831840, 2017, A, . Location in patent: Paragraph 0102; 0103; 0104.
[3] Patent: US2009/124666, 2009, A1, . Location in patent: Page/Page column 25-26.

[ 124236-37-9 ] Synthesis Path-Downstream 1~35

1
[ 67-56-1 ]
[ 201230-82-2 ]
[ 50488-42-1 ]
[ 124236-37-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	With triethylamine;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; at 80℃; under 3102.97 Torr; for 3h;	A solution of 2-bromo-5-(trifluoromethyl)pyridine (9 g, 40 mmol) in MeOH (130 mL) was added to Pd-dppf (0.813 g, 0.996 mmol) and Et3N (11 mL, 80 mmol) in a 250 mL pressure bottle. The mixture was pressurized with carbon monoxide (60 psi), and stirred 3 hr at 80 C. The reaction was cooled to ambient temperature, filtered, and the solvents evaporated at reduced pressure. The residue was partitioned between water and ethyl acetate. The separated organic layer was washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was chromatographed on silica gel (Analogix 40*240 column, 10%-40% EtOAc/hexanes eluant) to afford 8.52 g (104%) of the title compound as a white solid. 1H NMR (300 MHz, CDCl3) delta 9.01 (m, 1H), 8.28 (d, J=8.1, 1H), 8.12 (dd, J=2.1, 8.2, 1H), 4.06 (s, 3H). MS (ESI+) m/z 206 (M+H).

References: [1]Patent: US2009/124666,2009,A1 .Location in patent: Page/Page column 25.

2
[ 124236-37-9 ]
[ 31181-84-7 ]

Yield	Reaction Conditions	Operation in experiment
93%	With methanol; sodium tetrahydroborate; at 0 - 20℃;	IV. (5-trifluoromethyl-2-pyridinyl)methanol To a solution of <strong>[124236-37-9]methyl 5-trifluoromethyl-pyridine-2-carboxylate</strong> (2 g, 9.75 mmol) in MeOH (30 mL) at 0C was added NaB (738 mg, 19.5 mmol) portionwise. The mixture was stirred at room temperature for 2 h and concentrated. The residue was diluted with water (30 mL), acidified to pH~5 (IN HC1), extracted with EA (3 X 50 mL), dried, concentrated and purified by column chromatography on silica gel to give the title compound as a colorless oil (1.6 g, 93% yield): 1H NMR (400 MHz, CDC13) delta ppm 8.82 (s, 1H), 7.90-7.92 (m, 1H), 7.40-7.42 (m, 1H), 4.82-4.83 (m, 2H), 3.44-3.46 (m, 1H); ES-LCMS m/z 178 ( +H)+.
82.2%	With methanol; sodium tetrahydroborate; at 0 - 20℃; for 1h;	Compound SM (1.0 g, 4.87 mmol) was dissolved in MeOH (15 mL). At 0 C, NaBH4 (368.9 mg, 9.75 mmol) was added portionwise with stirring. Reaction at room temperature for 1 hour. TLC showed the reaction was completed. The pH was adjusted to 5-6 with 1 M HCl solution and the EA extracted (20 mL x 3). The combined organic phases were dried over anhydrous sodium sulfate, filtered and concentrated to give the title compound (710.0 mg, 82.2%).
72%		NaBH4 (0.369 g, 9.75 mmol) was added to Example 34A (1 g, 5 mmol) in EtOH (40 mL). The suspension was heated at reflux overnight. The reaction was cooled to ambient temperature and quenched with saturated NH4Cl solution. The mixture was diluted with water and extracted with EtOAc. The separated organic layer was washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was chromatographed on silica gel (Analogix 25*40 column, 30%-50% EtOAc/hexanes eluant) to afford 0.62 g (72%) of the title compound as a colorless oil. 1H NMR (300 MHz, CDCl3) delta 8.84 (s, 1H), 7.94 (dd, J=8.3, 2.1 1H), 7.43 (dd, J=8.2, 0.6 1H), 4.85 (d, J=5.2, 2H), 3.46 (t, J=5.3, 1H).

References: [1]Patent: WO2013/166621,2013,A1 .Location in patent: Page/Page column 48.
[2]Patent: CN106831840,2017,A .Location in patent: Paragraph 0102; 0103; 0104.
[3]Patent: US2009/124666,2009,A1 .Location in patent: Page/Page column 25-26.

3
[ 124236-37-9 ]
C₁₂H₁₀F₃NO₃ [ No CAS ]

References: [1]Organic Letters,2012,vol. 14,p. 1902 - 1905.

4
[ 124236-37-9 ]
C₁₆H₁₆F₃NO₃ [ No CAS ]

References: [1]Organic Letters,2012,vol. 14,p. 1902 - 1905.

5
[ 124236-37-9 ]
C₁₄H₁₂F₃NO₃ [ No CAS ]

References: [1]Organic Letters,2012,vol. 14,p. 1902 - 1905.

6
[ 124236-37-9 ]
C₁₄H₁₂F₃NO₂ [ No CAS ]

References: [1]Organic Letters,2012,vol. 14,p. 1902 - 1905.

7
[ 124236-37-9 ]
[ 756-79-6 ]
C₁₀H₁₁F₃NO₄P [ No CAS ]

References: [1]Organic Letters,2012,vol. 14,p. 1902 - 1905.

8
[ 124236-37-9 ]
[ 1415899-18-1 ]

Yield	Reaction Conditions	Operation in experiment
76%	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane;Reflux;	A mixture of <strong>[124236-37-9]5-(trifluoromethyl)-pyridine-2-carboxylic acid methyl ester</strong> (2.7 g, 13 mmol) and m-CPBA (CAN 937-14-4, 6.7 g, 39 mmol) in dry methylene chloride (30 mL) was stirred under reflux conditions overnight. Removal of the solvent in vacuo and purification of the obtained residue by column chromatography (silica gel, 15 g, 20% ethyl acetate in petroleum ether) provided the title compound (2.2 g, 76%) as light-yellow solid; MS (EI): m/e=222.1 [M+H]+.
76%	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane;Reflux;	A mixture of <strong>[124236-37-9]5-(trifluoromethyl)-pyridine-2-carboxylic acid methyl ester</strong> (2.7 g, 13 mmol) and m-CPBA (CAN 937-14-4, 6.7 g, 39 mmol) in dry methylene chloride (30 mL) was stirred under reflux conditions overnight. Removal of the solvent in vacuo and purification of the obtained residue by column chromatography (silica gel, 15 g, 20% ethyl acetate in petroleum ether) provided the title compound (2.2 g, 76%) as light-yellow solid; MS (EI): m/e = 222.1 [M+H]+.
76%	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane;Reflux;	b) 1 -Oxy-5-trifluoromethyl-pyridine-2-carboxylic acid methyl ester A mixture of <strong>[124236-37-9]5-(trifluoromethyl)-pyridine-2-carboxylic acid methyl ester</strong> (2.7 g, 13 mmol) and m-CPBA (CAN 937-14-4, 6.7 g, 39 mmol) in dry methylene chloride (30 mL) was stilTed under reflux conditions overnight. Removal of the solvent in vacuo and purification of the obtained residue by column chromatography (silica gel, 15 g, 20% ethyl acetate in petroleum ether) provided the title compound (2.2 g, 76%) as light-yellow solid; MS (El):mle = 222.1 [MHi.

46%	With urea hydrogen peroxide adduct; trifluoroacetic anhydride; In 1,2-dichloro-ethane; at -10 - 20℃;	[00173] Urea-H202 (161 mg, 1.72 mmol) was added into a solution of 56 (100 mg, 0.49 mmol) in DCE (4 mL). Trifluoroacetic anhydride (281 mg, 1.35 mmol) was added at -10 C for 2 h. The reaction mixture was stirred at 0 C for 2 h and then at rt overnight. The mixture was poured into ice-water (10 mL) and adjusted to pH 6-7 with 30% sodium hydroxide solution. The mixture was extracted with ethyl acetate (5 mL X 3). The combined organic layers were dried over anhydrous Na2504, filtered and concentrated under reduced pressure to afford 57 (50 mg, 46%) as a yellow solid, which was used for the next step directly without further purification. LC-MS tR = 0.372 mm in 5-95AB_1.5 mm chromatography (Welch MK RP-18e 25-2mm), MS (ESI) m/z 221.8 [M + H].
387mg	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 60℃; for 6h;	5-trifluoromethyl-2-pyridine carboxylic acid methyl ester (m) (1.03g, 5 . 0mmol) and meta-chloroperoxybenzoic acid (1.2g, 7 . 0mmol) dissolved in dichloromethane (15 ml) stirred at 60 C for 6 hours, to remove the solvent by silica gel column chromatography purification to obtain the product (n) (387 mg, 1 . 8mmol).

References: [1]Patent: US2012/316147,2012,A1 .Location in patent: Page/Page column 77.
[2]Patent: WO2012/168350,2012,A1 .Location in patent: Page/Page column 159.
[3]Patent: WO2014/86705,2014,A1 .Location in patent: Page/Page column 62.
[4]Patent: WO2014/179564,2014,A1 .Location in patent: Paragraph 00173.
[5]Patent: CN105218523,2016,A .Location in patent: Paragraph 0183; 0184; 0185; 0186.
[6]Patent: WO2019/149660,2019,A1 .Location in patent: Page/Page column 69.

9
[ 124236-37-9 ]
[ 1211518-35-2 ]

References: [1]Patent: US2012/316147,2012,A1 .
[2]Patent: WO2014/86705,2014,A1 .
[3]Patent: WO2019/149660,2019,A1 .

10
[ 124236-37-9 ]
[ 1415899-19-2 ]

References: [1]Patent: US2012/316147,2012,A1 .
[2]Patent: WO2012/168350,2012,A1 .
[3]Patent: WO2014/86705,2014,A1 .

11
[ 67-56-1 ]
[ 80194-69-0 ]
[ 124236-37-9 ]

Yield	Reaction Conditions	Operation in experiment
84%	With thionyl chloride;Reflux;	A solution of 5-(trifluoromethyl)-pyridine-2-carboxylic acid (CAN 80194-69-0, 3 g, 15.7 mmol) and sulfurous dichloride (0.1 mL) in methanol (30 mL) was stirred under reflux conditions overnight. Removal of the solvent provided the crude title compound which was purified by column chromatography (silica gel, 20 g, 10% ethyl acetate in petroleum ether) to obtain the title compound (2.7 g, 84%) as white solid; MS (EI): m/e=206.1 [M+H]+.
84%	With thionyl chloride;Reflux;	A solution of 5-(trifluoromethyl)-pyridine-2-carboxylic acid (CAN 80194-69-0, 3 g, 15.7 mmol) and sulfurous dichloride (0.1 mL) in methanol (30 mL) was stirred under reflux conditions overnight. Removal of the solvent provided the crude title compound which was purified by column chromatography (silica gel, 20 g, 10% ethyl acetate in petroleum ether) to obtain the title compound (2.7 g, 84%) as white solid; MS (EI): m/e = 206.1 [M+H]+.
84%	With thionyl chloride;Reflux;	a) 5- (Trifluoromethyl)-pyridine-2-carboxylic acid methyl ester A solution of 5-(trifluoromethyl)-pyridine-2-carboxylic acid (CAN 80194-69-0, 3 g, 15.7 mmol) and sulfurous dichloride (0.1 mL) in methanol (30 mL) was stirred under reflux conditions overnight. Removal of the solvent provided the crude title compound which5 was purified by column chromatography (silica gel, 20 g, 10% ethyl acetate in petroleum ether) to obtain the title compound (2.7 g, 84%) as white solid; MS (El): mle = 206.1 [MHi.

80%

With thionyl chloride; for 18h;Inert atmosphere; Reflux;

[00172] 50C12 (1.1 mL, 15.7 mmol) was added dropwise slowly to a solution of acid 55 (0.6 g, 3.1 mmol) in anhydrous methanol (40 mL). The mixture was stirred at reflux under N2 for 18 h. The solvent was removed under reduced pressure. Water (5 mL) and EtOAc (5 mL) were added to the mixture. The mixture was basified with sat. NaHCO3 solution to pH =7-8. After partition, the aqueous layer was extracted with EtOAc (3 X 3 mL), the combined organic layers were washed with brine (5 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford 56 (510 mg, 80%) as a pale yellow solid, which was used for the next step directly without further purification.

References: [1]Patent: US2012/316147,2012,A1 .Location in patent: Page/Page column 76.
[2]Patent: WO2012/168350,2012,A1 .Location in patent: Page/Page column 158; 159.
[3]Patent: WO2014/86705,2014,A1 .Location in patent: Page/Page column 61; 62.
[4]Patent: WO2014/179564,2014,A1 .Location in patent: Paragraph 00172.

12
[ 124236-37-9 ]
(5-(trifluoromethyl)pyridin-2-yl)methyl methanesulfonate [ No CAS ]