[ CAS No. 383907-17-3 ]

Name: 383907-17-3|3-Amino-2-methyl-6-(trifluoromethyl)pyridine|97%
Brand: Ambeed
SKU: A593363
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Cat. No.: {[proInfo.prAm]}

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Quality Control of [ 383907-17-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 383907-17-3 ]

SDS Specification

Alternatived Products of [ 383907-17-3 ]

Product Details of [ 383907-17-3 ]

CAS No. :	383907-17-3	MDL No. :	MFCD01311991
Formula :	C₇H₇F₃N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FUJKUIAVFVGTGS-UHFFFAOYSA-N
M.W :	176.14	Pubchem ID :	3521850
Synonyms :

Calculated chemistry of [ 383907-17-3 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.29
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	38.61
TPSA :	38.91 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.32 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.41
Log Po/w (XLOGP3) :	1.49
Log Po/w (WLOGP) :	3.15
Log Po/w (MLOGP) :	1.25
Log Po/w (SILICOS-IT) :	2.09
Consensus Log Po/w :	1.88

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.17
Solubility :	1.18 mg/ml ; 0.00669 mol/l
Class :	Soluble
Log S (Ali) :	-1.91
Solubility :	2.14 mg/ml ; 0.0122 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.94
Solubility :	0.204 mg/ml ; 0.00116 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.54

Safety of [ 383907-17-3 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P261-P301+P310-P305+P351+P338	UN#:	2811
Hazard Statements:	H301-H315-H319-H335	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 383907-17-3 ]

* 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 [ 383907-17-3 ]

[ 383907-17-3 ] Synthesis Path-Downstream 1~41

1
[ 624-28-2 ]
[ 383907-17-3 ]
[ 956136-81-5 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate In 1,4-dioxane at 100℃; for 18h; Sealed vessel;	4-12.A 2,5-dibromopyridine (474 mg, 2 mmol) and 2-Methyl-6-trifluoromethyl-pyridin-3-ylamine (352 g, 2 mmol) were dissolved in 1 ,4-dioxane (4 mL) in a pressure vessel. Pd2dba3 (55 mg, 0.06 mmol) and XANTPHOS (46 mg, 0.08 mmol) were added, followed by cesium carbonate (1.3 g, 4 mmol). The mixture was sparged with nitrogen for 10 minutes, then the vessel was sealed and heated at 100 0C for 18 hours. The mixture was partitioned between EtOAc and saturated aqueous NH4CI, then the organic layer was washed with brine, dried with magnesium sulfate, filtered, and concentrated via rotary evaporation. The crude material was purified via column chromatography on silica gel, eluting with a gradient of EtOAc/hexanes (7-60%) to obtain the target compound as a solid: 1H NMR (400 MHz, CDCI3) δ ppm 2.62 (s, 3 H) 6.36 (br. s., 1 H) 6.75 (d. J=8.59 Hz, 1 H) 7.53 (d, J=8.34 Hz, 1 H) 7.69 (dd, J=8.84, 2.53 Hz, 1 H) 8.32 - 8.37 (m, 2 H); MS (M+H)+ 334.7.

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2007/126957, 2007, A2 Location in patent: Page/Page column 98-99

2
[ 383907-17-3 ]
[ 1934-75-4 ]
C₉H₈N₅F₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride In water at 45℃;

Reference： [1]Perez-Medrano, Arturo; Brune, Michael E.; Buckner, Steven A.; Coghlan, Michael J.; Fey, Thomas A.; Gopalakrishnan, Murali; Gregg, Robert J.; Kort, Michael E.; Scott, Victoria E.; Sullivan, James P.; Whiteaker, Kristi L.; Carroll, William A. [Journal of Medicinal Chemistry, 2007, vol. 50, # 24, p. 6265 - 6273]

3
2-methyl-6-(trifluoromethyl)nicotinamide [ No CAS ]
[ 383907-17-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; bromine In tetrahydrofuran at 5 - 70℃;

4
[ 383907-17-3 ]
[ 944317-26-4 ]

Yield	Reaction Conditions	Operation in experiment
	With iodine; isopentyl nitrite In chloroform at 20 - 80℃; for 4.5h;	10.A A mixture of 3-amino-2-methyl-6-(trifluoromethyl)pyridine (500 mg, 2.84 mmol), isoamyl nitrite 760 μL, 5.68 mmol) and iodide (793 mg, 3.12 mmol) in dry CHCl3 (10 mL) was stirred at room temperature for 0.5 h. The mixture was heated at 80 0C under N2 for 4 h. The reaction mixture was quenched with saturated Na2S2O3 then partitioned between CH2Cl2 and water. The organic layer was dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography (Si, 1% EtOAc in hexanes) to afford 3-iodo-2-methyl~6-(trifluoromethyl)pyridine. LCMS calc. = 288.0; found = 288.0 (M+l)+. 1H NMR (500 MHz, CDCl3) δ 8.25 (d, J = 8.0 Hz3 1 H); 7.22 (d, J= 8.1 Hz, 1 H); 2.83 (s, 3 H).

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2007/81569, 2007, A2 Location in patent: Page/Page column 43

5
[ 383907-17-3 ]
[ 463-71-8 ]
[ 1140496-11-2 ]
[ 1140495-47-1 ]

Yield	Reaction Conditions	Operation in experiment
26.9%	Stage #1: 2-methyl-6-(trifluoromethyl)pyridin-3-amine; thiophosgene With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 1h; Stage #2: (R)-4-(4-chlorobenzyl)-3-ethyl-5-(pyrrolidin-2-yl)-4H-1,2,4-triazole hydrochloride In dichloromethane at 0 - 20℃;	56 Example 56 (R)-2-(4-(4-chlorobenzyl)-5-methyl-4H-1,2,4-triazol-3-yl)-N-(2-methyl-6-(trifluoromethyl)pyridin-3-yl)pyrrolidine-1-carbothioamide. To a stirring solution of thiophosgene (0.23 mL, 3 mmol) in 50 mL of CH2Cl2 at 0° C. was added dropwise a mixed solution of 2-methyl-6-(trifluoromethyl)pyridin-3-amine (0.528 g, 3 mmol) and N,N-diisopropylethylamine (0.522 mL, 3 mmol) in dichloromethane (10 mL). The reaction mixture was stirred at 0° C., warming up to room temperature within an hour. Then the mixture was cooled at 0° C. and to it was added a solution of the (R)-4-(4-chlorobenzyl)-3-ethyl-5-(pyrrolidin-2-yl)-4H-1,2,4-triazole HCl salt (1.05 g, 3 mmol) and N,N-diisopropylethylamine (1.044 mL, 6 mmol) in dichloromethane (10 mL) slowly. The resulting mixture was stirred 0° C. for 30 minutes, then at room temperature overnight. The reaction mixture was treated with sat. aqueous NaHCO3 (10 mL) and brine, dried over Na2SO4, and concentrated in vacuo. Flash chromatography purification (Hex/EtOAc with 10% of MeOH) afforded the desired product as yellow solid (0.4 g, 26.9%). 1H NMR (300 MHz, CDCl3) 1.96-2.19 (m, 3H), 2.30 (s, 3H), 2.56 (s, 3H), 2.69-2.72 (m, 1H), 3.74-3.77 (m, 1H), 4.21-4.25 (m, 1H), 5.02-5.08 (d, 1H), 5.51-5.57 (d, 1H), 5.59-5.60 (d, 1H), 7.00-7.03 (d, 2H), 7.31-7.35 (dd, 2H), 7.44-7.46 (d, 1H), 7.66 (s, 1H), 7.77-7.80 (d, 1H). MS: calculated: 494.96, found (MH+): 495.0.

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - US2009/93472, 2009, A1 Location in patent: Page/Page column 37

6
[ 117519-09-2 ]
[ 13061-96-6 ]
[ 383907-17-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 1890 - 1894

7
[ 383907-17-3 ]
[ 1173435-13-6 ]
[ 1224432-41-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hexamethyldisilazane In tetrahydrofuran

Reference： [1]Location in patent: scheme or table Hartz, Richard A.; Ahuja, Vijay T.; Schmitz, William D.; Molski, Thaddeus F.; Mattson, Gail K.; Lodge, Nicholas J.; Bronson, Joanne J.; Macor, John E. [Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 6, p. 1890 - 1894]

8
[ 383907-17-3 ]
[ 108-24-7 ]
[ 1383735-00-9 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine In dichloromethane for 144h;	To a solution of K-1 (5.00 g, 28.4 mmol) in DCM (25 mL) is added acetic anhydride (3.30 mL, 34.2 mmol) followed by DIPEA (5.6 mL, 32.2 mmol) and DMAP (25.0 mg, 0.20 mmol). After 6 days, the reaction is concentrated and diluted with water, made basic with NaHCO3, and extracted with EtOAc (3 x 50 mL). The combined organic layers are washed with brine (2 x 40 mL), dried over magnesium sulfate, filtered and concentrated. The crude material is purified by silica gel chromatography eluting with DCM -heptane (1: 1) and then ethyl acetate. Mixed fractions are purified by silica gel chromatography eluting with EtO Ac-heptane (1:9, then 2:8, then 100:0) to provide K-2.

Reference： [1]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - WO2012/87782, 2012, A1 Location in patent: Page/Page column 59

9
[ 383907-17-3 ]
[ 1256836-65-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine / dmap / dichloromethane / 144 h 2.1: acetic anhydride; potassium acetate; acetic acid; isopentyl nitrite / toluene / 1 h / Reflux 2.2: 1 h / Reflux
	Multi-step reaction with 3 steps 1: triethylamine / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere 2: potassium acetate; acetic anhydride / toluene / 16 h / 80 °C 3: water; sodium hydroxide / tetrahydrofuran; methanol / 2 h / 20 °C

Reference： [1]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - WO2012/87782, 2012, A1
[2]Current Patent Assignee: NURIX THERAPEUTICS INC - WO2021/21761, 2021, A1

10
[ 383907-17-3 ]
[ 1383735-01-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine / dmap / dichloromethane / 144 h 2.1: acetic anhydride; potassium acetate; acetic acid; isopentyl nitrite / toluene / 1 h / Reflux 2.2: 1 h / Reflux 3.1: potassium carbonate / cis-N,N'-dimethyl-1,2-diaminocyclohexane; copper(l) iodide / N,N-dimethyl-formamide / 1.5 h / 140 °C / microwave irradiation

Reference： [1]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - WO2012/87782, 2012, A1

11
[ 383907-17-3 ]
[ 1383735-52-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: N-ethyl-N,N-diisopropylamine / dmap / dichloromethane / 144 h 2.1: acetic anhydride; potassium acetate; acetic acid; isopentyl nitrite / toluene / 1 h / Reflux 2.2: 1 h / Reflux 3.1: potassium carbonate / cis-N,N'-dimethyl-1,2-diaminocyclohexane; copper(l) iodide / N,N-dimethyl-formamide / 1.5 h / 140 °C / microwave irradiation 4.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / 1,4-dioxane; methanol / 3 h / 50 °C / 15514.9 - 18100.7 Torr

Reference： [1]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - WO2012/87782, 2012, A1

12
[ 383907-17-3 ]
[ 1383735-56-5 ]
[ 1383735-55-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: N-ethyl-N,N-diisopropylamine / dmap / dichloromethane / 144 h 2.1: acetic anhydride; potassium acetate; acetic acid; isopentyl nitrite / toluene / 1 h / Reflux 2.2: 1 h / Reflux 3.1: potassium carbonate / cis-N,N'-dimethyl-1,2-diaminocyclohexane; copper(l) iodide / N,N-dimethyl-formamide / 1.5 h / 140 °C / microwave irradiation 4.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / 1,4-dioxane; methanol / 3 h / 50 °C / 15514.9 - 18100.7 Torr 5.1: AD column / isopropyl alcohol; n-heptane / Resolution of racemate

Reference： [1]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - WO2012/87782, 2012, A1

13
[ 383907-17-3 ]
4-bromo-2-methyl-6-(trifluoromethyl)pyridin-3-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
4 g	With N-Bromosuccinimide In acetonitrile at 20℃; for 1.5h;	4.1 Step 1: Synthesis of 4-bromo-2-methyl-6-(trifluoromethyl)pyridin-3-amine To a solution of 3.0 g of 2-methyl-6-(trifluoromethyl)pyridin-3-amine in 30 ml of acetonitrile, 3.03 g of N-bromosuccinimide was added at room temperature. After the addition, the reaction mixture was stirred at room temperature for 1.5 hours. After the reaction, the solvent was evaporated under reduced pressure. The resulting residue was purified by preparative medium pressure liquid chromatography using n-hexane/ethyl acetate (with a gradient of from 10:0 to 50:50) as the eluent to obtain 4.0 g of the desired product as a brown solid. Melting point: 40-41° C. 1H-NMR (CDCl3): δ7.61 (s, 1H), 4.40 (brs, 2H), 2.52 (s, 3H).
4.0 g	With N-Bromosuccinimide In acetonitrile at 20℃; for 1.5h;	4.1 Step 1: Synthesis of 4-bromo-2-methyl-6-(trifluoromethyl)pyridin-3-amine To a solution of 3.0 g of 2-methyl-6-(trifluoromethyl)pyridin-3-amine in 30 ml of acetonitrile was added 3.03 g of N-bromosuccinimide at room temperature. After the addition was complete, the reaction mixture was stirred at room temperature for 1.5 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient of 100:0 to 50:50) to give 4.0 g of the desired product in brown.Obtained as a colored solid.

Reference： [1]Current Patent Assignee: NISSAN CHEMICAL CORPORATION - US2018/22760, 2018, A1 Location in patent: Paragraph 1145; 1146; 1147
[2]Current Patent Assignee: NISSAN CHEMICAL CORPORATION - JP2020/111539, 2020, A Location in patent: Paragraph 0628-0629

14
[ 383907-17-3 ]
4-bromo-N,2-dimethyl-6-(trifluoromethyl)pyridin-3-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide / acetonitrile / 1.5 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 20 °C / Cooling with ice 2.2: 0.5 h / 20 °C / Cooling with ice
	Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide / acetonitrile / 1.5 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 20 °C / Cooling with ice 2.2: 0.5 h / 20 °C / Cooling with ice

Reference： [1]Current Patent Assignee: NISSAN CHEMICAL CORPORATION - US2018/22760, 2018, A1
[2]Current Patent Assignee: NISSAN CHEMICAL CORPORATION - JP2020/111539, 2020, A

15
[ 383907-17-3 ]
2-[3-(ethylthio)-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3,4-dimethyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: N-Bromosuccinimide / acetonitrile / 1.5 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 20 °C / Cooling with ice 2.2: 0.5 h / 20 °C / Cooling with ice 3.1: copper acetylacetonate; caesium carbonate; ammonium hydroxide / 1-methyl-pyrrolidin-2-one / 1 h / 140 °C / Autoclave; Sealed tube 4.1: pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / 20 °C 5.1: acetic acid / 3 h / Reflux
	Multi-step reaction with 5 steps 1.1: N-Bromosuccinimide / acetonitrile / 1.5 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 20 °C / Cooling with ice 2.2: 0.5 h / 20 °C / Cooling with ice 3.1: ammonium hydroxide; copper acetylacetonate; acetylacetone / 1-methyl-pyrrolidin-2-one / 1 h / 20 - 140 °C / Autoclave 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap; pyridine / 20 °C 5.1: acetic acid / 3 h / Reflux

Reference： [1]Current Patent Assignee: NISSAN CHEMICAL CORPORATION - US2018/22760, 2018, A1
[2]Current Patent Assignee: NISSAN CHEMICAL CORPORATION - JP2020/111539, 2020, A

16
[ 383907-17-3 ]
2-[3-(ethylsulfonyl)-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3,4-dimethyl-6-(trifluoromethyl)-3H-imidazo[4,5-c]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: N-Bromosuccinimide / acetonitrile / 1.5 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 20 °C / Cooling with ice 2.2: 0.5 h / 20 °C / Cooling with ice 3.1: copper acetylacetonate; caesium carbonate; ammonium hydroxide / 1-methyl-pyrrolidin-2-one / 1 h / 140 °C / Autoclave; Sealed tube 4.1: pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / 20 °C 5.1: acetic acid / 3 h / Reflux 6.1: 3-chloro-benzenecarboperoxoic acid / chloroform; water / 2 h / 20 °C / Cooling with ice
	Multi-step reaction with 6 steps 1.1: N-Bromosuccinimide / acetonitrile / 1.5 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 20 °C / Cooling with ice 2.2: 0.5 h / 20 °C / Cooling with ice 3.1: ammonium hydroxide; copper acetylacetonate; acetylacetone / 1-methyl-pyrrolidin-2-one / 1 h / 20 - 140 °C / Autoclave 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap; pyridine / 20 °C 5.1: acetic acid / 3 h / Reflux 6.1: 3-chloro-benzenecarboperoxoic acid / chloroform; water / 2 h / 20 °C / Cooling with ice

Reference： [1]Current Patent Assignee: NISSAN CHEMICAL CORPORATION - US2018/22760, 2018, A1
[2]Current Patent Assignee: NISSAN CHEMICAL CORPORATION - JP2020/111539, 2020, A

17
[ 383907-17-3 ]
3-(ethylthio)-N-[2-methyl-3-(methylamino)-6-(trifluoromethyl) pyridin-4-yl]-6-(trifluoromethyl)imidazo[ 1,2-a] pyridine-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: N-Bromosuccinimide / acetonitrile / 1.5 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 20 °C / Cooling with ice 2.2: 0.5 h / 20 °C / Cooling with ice 3.1: copper acetylacetonate; caesium carbonate; ammonium hydroxide / 1-methyl-pyrrolidin-2-one / 1 h / 140 °C / Autoclave; Sealed tube 4.1: pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / 20 °C
	Multi-step reaction with 4 steps 1.1: N-Bromosuccinimide / acetonitrile / 1.5 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 20 °C / Cooling with ice 2.2: 0.5 h / 20 °C / Cooling with ice 3.1: ammonium hydroxide; copper acetylacetonate; acetylacetone / 1-methyl-pyrrolidin-2-one / 1 h / 20 - 140 °C / Autoclave 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap; pyridine / 20 °C

Reference： [1]Current Patent Assignee: NISSAN CHEMICAL CORPORATION - US2018/22760, 2018, A1
[2]Current Patent Assignee: NISSAN CHEMICAL CORPORATION - JP2020/111539, 2020, A

18
[ 383907-17-3 ]
N<SUP>3</SUP>,2-dimethyl-6-(trifluoromethyl)pyridine-3,4-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: N-Bromosuccinimide / acetonitrile / 1.5 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 20 °C / Cooling with ice 2.2: 0.5 h / 20 °C / Cooling with ice 3.1: copper acetylacetonate; caesium carbonate; ammonium hydroxide / 1-methyl-pyrrolidin-2-one / 1 h / 140 °C / Autoclave; Sealed tube
	Multi-step reaction with 3 steps 1.1: N-Bromosuccinimide / acetonitrile / 1.5 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 20 °C / Cooling with ice 2.2: 0.5 h / 20 °C / Cooling with ice 3.1: ammonium hydroxide; copper acetylacetonate; acetylacetone / 1-methyl-pyrrolidin-2-one / 1 h / 20 - 140 °C / Autoclave

Reference： [1]Current Patent Assignee: NISSAN CHEMICAL CORPORATION - US2018/22760, 2018, A1
[2]Current Patent Assignee: NISSAN CHEMICAL CORPORATION - JP2020/111539, 2020, A

19
[ 383907-17-3 ]
2-(pyridin-2-yl)-5-(trifluoromethyl)-2H-pyrazolo[4,3-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: 18-crown-6 ether; isopentyl nitrite; potassium acetate / chloroform / 2 h / 100 °C 2.1: potassium carbonate; water / methanol / 1.5 h / 20 - 50 °C 3.1: potassium carbonate / dimethyl sulfoxide / 0.5 h / 20 °C 3.2: 48 h / 80 °C