[ CAS No. 171197-80-1 ] {[proInfo.proName]}

Name: 171197-80-1|2-Fluoro-5-iodopyridine|98%
Brand: Ambeed
SKU: A153880
Price: 5.0 USD
Availability: InStock
Rating: 90 (40 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

DV 2D 3D

3d Animation Molecule Structure of 171197-80-1

Structure of 171197-80-1 * Storage: {[proInfo.prStorage]}

Please Login or Create an Account to: See VIP prices and availability

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

* Shipping: {[proInfo.prShipping]}

For Research Only 120K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 171197-80-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 171197-80-1 ]

SDS Specification

Alternatived Products of [ 171197-80-1 ]

Product Details of [ 171197-80-1 ]

CAS No. :	171197-80-1	MDL No. :	MFCD03095301
Formula :	C₅H₃FIN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GYZNHUNWABYAPO-UHFFFAOYSA-N
M.W :	222.99	Pubchem ID :	2783179
Synonyms :

Calculated chemistry of [ 171197-80-1 ] Expand+

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	36.91
TPSA :	12.89 Å²

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) :	-6.28 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.73
Log Po/w (XLOGP3) :	1.94
Log Po/w (WLOGP) :	2.25
Log Po/w (MLOGP) :	1.85
Log Po/w (SILICOS-IT) :	2.83
Consensus Log Po/w :	2.12

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.0
Solubility :	0.223 mg/ml ; 0.001 mol/l
Class :	Soluble
Log S (Ali) :	-1.84
Solubility :	3.26 mg/ml ; 0.0146 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.26
Solubility :	0.122 mg/ml ; 0.000548 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.22

Safety of [ 171197-80-1 ]

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 [ 171197-80-1 ]

* 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 [ 171197-80-1 ]
Downstream synthetic route of [ 171197-80-1 ]

[ 171197-80-1 ] Synthesis Path-Upstream 1~8

1
[ 540-80-7 ]
[ 109-63-7 ]
[ 1827-27-6 ]
[ 171197-80-1 ]

Yield	Reaction Conditions	Operation in experiment
59%	With Ki; sodium thiosulfate In 1,2-dimethoxyethane; acetonitrile	12c. 2-Fluoro-5-iodopyridine 5-Amino-2-fluoropyridine (990 mg, 8.83 mmol, from step 12b) in DME (5 mL) was added dropwise to a solution of boron trifluoride diethyl etherate (1.6 mL, 13.2 mmol) at -10° C. After stirring for 15 min, t-butyl nitrite in DME (15 mL) was carefully added to the reaction mixture while maintaining the temperature below -5° C. After complete addition the temperature was allowed to gradually warm to 5° C. over 1 hour. The solution was recooled to -10° C., the residue was triturated with pentane (2*) and Et₂ O, then all solvents were removed in vacuo. The crude diazonium tetrafluoroborate salt was dissolved in acetonitrile (50 mL), KI was added (1.6 g, 9.7 mmol) and the mixture was stirred for 24 hours. A solution of 10percent sodium thiosulfate was carefully added, the mixture was poured over Et₂ O and the phases separated. The organic phase was dried (MgSO₄) and concentrated, and the residue was chromatographed (silica gel; EtOAc/hexane, 1:20) to afford a white solid (1.2 g, 59percent): ¹ H NMR (CDCl₃, 300 MHz) δ6.79 (dd, J=8.4, 2.6 Hz, 1H), 8.04 (ddd, J=8.4, 7.4 2.6 Hz, 1H), 8.43 (dd, 2.6, 0.7 Hz, 1H).

Reference： [1] Patent: US5733912, 1998, A,

2
[ 20511-12-0 ]
[ 171197-80-1 ]

Reference： [1] Journal of Medicinal Chemistry, 2001, vol. 44, # 13, p. 2229 - 2237
[2] Tetrahedron, 2002, vol. 58, # 14, p. 2885 - 2890
[3] Bioorganic and Medicinal Chemistry, 1999, vol. 7, # 3, p. 467 - 479

3
[ 69045-79-0 ]
[ 171197-80-1 ]

Reference： [1] Organic Letters, 2015, vol. 17, # 8, p. 1866 - 1869
[2] Journal of Organic Chemistry, 2015, vol. 80, # 24, p. 12137 - 12145

4
[ 766-11-0 ]
[ 171197-80-1 ]

Reference： [1] Journal of the American Chemical Society, 2015, vol. 137, # 33, p. 10480 - 10483

5
[ 171197-80-1 ]
[ 351019-18-6 ]

Reference： [1] Journal of Medicinal Chemistry, 2001, vol. 44, # 13, p. 2229 - 2237
[2] Tetrahedron, 2002, vol. 58, # 14, p. 2885 - 2890

6
[ 76-09-5 ]
[ 171197-80-1 ]
[ 444120-95-0 ]

Reference： [1] Tetrahedron, 2002, vol. 58, # 14, p. 2885 - 2890

7
[ 171197-80-1 ]
[ 853909-08-7 ]

Reference： [1] Patent: US2014/30191, 2014, A1,
[2] European Journal of Medicinal Chemistry, 2016, vol. 107, p. 153 - 164

8
[ 171197-80-1 ]
[ 411235-57-9 ]
[ 1034467-80-5 ]

Yield	Reaction Conditions	Operation in experiment
63%	With potassium phosphate In water; toluene at 100℃; for 4 h;	Preparation 46; 5-Cyclopropyl-2-fluoro-pyridine; In a flask, combine 2-fluoro-5-iodo-pyridine (1.12 g, 5 mmol), cyclopropylboronic acid (645 mg, 7.5 mmol), palladium acetate (56 mg, 0.25 mmol), potassium phosphate (3.2 g, 15 mmol), and toluene-water (20: 1, 21 mL). Heat the mixture at 100 ⁰C for 4 hours. Dilute the mixture with chloroform-isopropanol (3: 1, 100 mL). Wash the organic phase with saturated aqueous sodium chloride and water. Dry the mixture over sodium sulfate. Concentrate the solution in vacuo to a brown oil. Purify by column chromatography (20 percent ethyl acetate in hexane) to afford the title compound (430 mg, 63 percent) as a pale yellow oil. ¹H νMR (400 MHz-CDCl₃) δ 7.99 (d, J= 3 Hz, IH), 7.39 (td, J= 3, 5 Hz, IH), 6.79 (dd, J= 3, 8 Hz, IH), 0.96-1.02 (m, 2H), 0.63-0.69 (m, 2H).
63%	With potassium phosphate In water; toluene at 100℃; for 4 h;	Preparation 145-Cyclopropyl-2-fluoro-pyridineCombine 2-fluoro-5-iodo-pyridine (1.12 g, 5 mmol), cyclopropylboronic acid (645 mg, 7.5 mmol), palladium acetate (56 mg, 0.25 mmol) and potassium phosphate (3.2 g, 15 mmol) in toluene/water (20: 1, 21 mL). Heat the mixture at 100 ⁰C for 4 h. Dilute the mixture with chloroform-IPA (3:1, 100 mL). Wash the organic phase with saturated aqueous sodium chloride and water. Dry the mixture over sodium sulfate. Concentrate the solution in vacuo to a brown oil. Purify by column chromatography (20 percent ethyl acetate in hexane) to afford the title compound as a pale yellow oil (430 mg, 63 percent).

Reference： [1] Patent: WO2008/76705, 2008, A1, . Location in patent: Page/Page column 19
[2] Patent: WO2008/144222, 2008, A2, . Location in patent: Page/Page column 13

[ 171197-80-1 ] Synthesis Path-Downstream 1~23

1
[ 76-09-5 ]
[ 171197-80-1 ]
[ 444120-95-0 ]

Reference： [1]Tetrahedron,2002,vol. 58,p. 2885 - 2890

2
[ 147459-52-7 ]
[ 171197-80-1 ]
tert-butyl[1-(5-iodopyridin-2-yl)-3-methylpyrrolidin-3-yl]carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With potassium carbonate; In dimethyl sulfoxide; at 100.0℃; for 16.0h;	A solution of 2-fluoro-5-iodo pyridine (590 mg, 2.65 mmol) in DMSO (3 ml) was treated with potassium carbonate (731 mg, 5.3 mmol) and <strong>[147459-52-7]tert-butyl (3-methylpyrrolidin-3-yl)carbamate</strong> (Chem. Pharm. Bull 1996, 44(7) 1376, 583 mg, 2.91 mmol). The reaction was heated to 100 C. for 16 hours and then cooled to room temperature. Water (20 ml) was added and the product was extracted with ethyl acetate (220 ml). The combined organics were washed with brine (320 ml), dried (Na2SO4) and concentrated in vacuo to a brown oil. Purification on an SCX column (non-basic impurities with methanol, basic products eluted with 2M ammonia in methanol) gave the title compound as a pale brown oil (790 mg, 74%). 1H NMR (400 MHz, CD3OD) delta ppm 1.42 (s, 9H), 1.45 (s, 3H), 1.93-2.01 (m, 1H), 2.30-2.38 (m, 1H), 3.33-3.36 (m, 1H), 3.43-3.51 (m, 2H), 3.71-3.74 (d, 1H), 6.33-6.35 (d, 1H), 7.67-7.70 (dd, 1H), 8.14 (d, 1H) LRMS m/z (APCI) 404 [MH+].

Reference： [1]Patent: US2008/85884,2008,A1 .Location in patent: Page/Page column 70

3
[ 113451-59-5 ]
[ 171197-80-1 ]
[ 286946-57-4 ]

Yield	Reaction Conditions	Operation in experiment
21%	With sodium t-butanolate;(S)-(2'-methoxy-[1,1'-binaphthalen]-2-yl)diphenylphosphane; tris-(dibenzylideneacetone)dipalladium(0); In toluene; at 80℃; for 5h;	Example 30A tert-butyl (1S,4S)-5-(6-fluoro-3-pyridinyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate tert-Butyl (1S,4S)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (0.300 g, 1.01 mmol), prepared as described in (J. Med. Chem., (1988) 31, 1598-1611), in anhydrous toluene (30ml) was treated with 2-fluoro-5-iodopyridine (0.34g, 1.52 mmol), available as described in (US 5,733,912), Pd2(dba)3 (0.028 g, 0.03 mmol), (S)-(-)-2-(diphenylphosphino)-2'-methoxy-1,1'-binaphthyl (0.028 g, 0.06 mmol), available from Strem Chemicals, and sodium tert-butoxide (0.248 g, 2.58 mmol). The reaction mixture was heated at 80C for 5 hours. The reaction mixture was poured into diethyl ether (100 mL), washed with brine (100ml), dried (MgSO4), and concentrated under reduced pressure. The residue was purified by chromatography on SiO2 (3%MeOH/CH2Cl2) to provide the title compound (0.095g, 21% yield) as a yellow oil. MS (DCI/NH3) m/z 276 (M+H)+.
21%	With (S)-(2'-methoxy-[1,1'-binaphthalen]-2-yl)diphenylphosphane; sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); In toluene; at 80℃; for 5h;	tert-Butyl (1S,4S)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (0.300 g, 1.01 mmol), prepared as described in (J. Med. Chem., (1988) 31, 1598-1611), in anhydrous toluene (30 ml) was treated with 2-fluoro-5-iodopyridine (0.34 g, 1.52 mmol), available as described in (U.S. Pat. No. 5,733,912), Pd2(dba)3 (0.028 g, 0.03 mmol), (S)-(-)-2-(diphenylphosphino)-2'-methoxy-1,1'-binaphthyl (0.028 g, 0.06 mmol), available from Strem Chemicals, and sodium tert-butoxide (0.248 g, 2.58 mmol). The reaction mixture was heated at 80 C. for 5 hours. The reaction mixture was poured into diethyl ether (100 mL), washed with brine (100 ml), dried (MgSO4), and concentrated under reduced pressure. The residue was purified by chromatography on SiO2 (3%MeOH/CH2Cl2) to provide the title compound (0.095 g, 21% yield) as a yellow oil. MS (DCI/NH3) m/z 276 (M+H)+.

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 3627 - 3644
[2]Patent: EP1147112,2003,B1 .Location in patent: Page/Page column 25
[3]Patent: US2003/225268,2003,A1 .Location in patent: Page 25

4
[ 134003-84-2 ]
[ 171197-80-1 ]
[ 286946-62-1 ]

Yield	Reaction Conditions	Operation in experiment
		The product from Example 15B and 2-fluoro-5-iodopyridine were processed as described in Example 30A to provide the title compound. MS (DCIINH3) m/z 294 (M+H)+.

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 3627 - 3644
[2]Journal of Medicinal Chemistry,2007,vol. 50,p. 3627 - 3644
[3]Patent: US2003/225268,2003,A1 .Location in patent: Page 26

5
[ 171197-80-1 ]
[ 411235-57-9 ]
[ 1034467-80-5 ]

Yield	Reaction Conditions	Operation in experiment
63%	With potassium phosphate;palladium diacetate; In water; toluene; at 100℃; for 4h;	Preparation 46; 5-Cyclopropyl-2-fluoro-pyridine; In a flask, combine 2-fluoro-5-iodo-pyridine (1.12 g, 5 mmol), cyclopropylboronic acid (645 mg, 7.5 mmol), palladium acetate (56 mg, 0.25 mmol), potassium phosphate (3.2 g, 15 mmol), and toluene-water (20: 1, 21 mL). Heat the mixture at 100 0C for 4 hours. Dilute the mixture with chloroform-isopropanol (3: 1, 100 mL). Wash the organic phase with saturated aqueous sodium chloride and water. Dry the mixture over sodium sulfate. Concentrate the solution in vacuo to a brown oil. Purify by column chromatography (20 % ethyl acetate in hexane) to afford the title compound (430 mg, 63 %) as a pale yellow oil. 1H nuMR (400 MHz-CDCl3) delta 7.99 (d, J= 3 Hz, IH), 7.39 (td, J= 3, 5 Hz, IH), 6.79 (dd, J= 3, 8 Hz, IH), 0.96-1.02 (m, 2H), 0.63-0.69 (m, 2H).
63%	With potassium phosphate;palladium diacetate; In water; toluene; at 100℃; for 4h;	Preparation 145-Cyclopropyl-2-fluoro-pyridineCombine 2-fluoro-5-iodo-pyridine (1.12 g, 5 mmol), cyclopropylboronic acid (645 mg, 7.5 mmol), palladium acetate (56 mg, 0.25 mmol) and potassium phosphate (3.2 g, 15 mmol) in toluene/water (20: 1, 21 mL). Heat the mixture at 100 0C for 4 h. Dilute the mixture with chloroform-IPA (3:1, 100 mL). Wash the organic phase with saturated aqueous sodium chloride and water. Dry the mixture over sodium sulfate. Concentrate the solution in vacuo to a brown oil. Purify by column chromatography (20 % ethyl acetate in hexane) to afford the title compound as a pale yellow oil (430 mg, 63 %).

Reference： [1]Patent: WO2008/76705,2008,A1 .Location in patent: Page/Page column 19
[2]Patent: WO2008/144222,2008,A2 .Location in patent: Page/Page column 13

6
[ 4426-11-3 ]
[ 171197-80-1 ]
[ 1257637-93-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hexamethyldisilazane; In toluene; at 0 - 20℃;Inert atmosphere;	In a dry flask under argon, 2-fluoro-5-iodo-pyridine (3.85 g, 17.3 mmol) and <strong>[4426-11-3]cyclobutanecarbonitrile</strong> (1.40 g, 17 mmol) were dissolved in dry toluene (15 mL). The solution was cooled to O C and sodium bis(trimethylsilyl)amide (1.0 M, 19 mL, 19 mmol) was added dropwise over 15 min. After Ih, the solution was allowed to warm to room temperature and stirred for 26 h. The reaction was diluted with saturated aqueous NH4Cl (10 mL) and CH2Cl2 (10 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2 (2 x 10 mL). The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo to yield 4.0 g of l-(5-iodo-pyridin-2-yl)-<strong>[4426-11-3]cyclobutane carbonitrile</strong> as a viscous, light brown oil, m/z 285.4 [M + H]+.

Reference： [1]Patent: WO2010/141273,2010,A1 .Location in patent: Page/Page column 42-43

7
[ 19006-81-6 ]
[ 171197-80-1 ]
C₁₆H₁₁FN₂O [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 2464 - 2469

8
[ 10199-68-5 ]
[ 171197-80-1 ]
[ 1393125-40-0 ]

Yield	Reaction Conditions	Operation in experiment
94%	With potassium carbonate; In N,N-dimethyl-formamide; at 85℃; for 21h;	Intermediate (24): 5-iodo-2-(4-phenyl-1H-pyrazol-1-yl)pyridine A mixture of 2-fluoro-5-iodopyridine (368.3 mg, 1.652 mmol), <strong>[10199-68-5]4-phenyl-1H-pyrazole</strong> (238.2 mg, 1.652 mmol), and potassium carbonate (457 mg, 3.30 mmol) in N,N-dimethylformamide (3.30 mL) was heated to 85 C. for 21 hours. The reaction was then concentrated and the crude residue diluted with water and ethyl acetate. The layers were separated and the aqueous was extracted two more times with ethyl acetate. The combined organics were dried over magnesium sulfate, filtered, and concentrated to give 5-iodo-2-(4-phenyl-1H-pyrazol-1-yl)pyridine (537.2 mg, 94%) as a white solid. 1H NMR (400 MHz, CDCl3, delta): 8.76 (s, 1H), 8.61 (d, J=1.8 Hz, 1H), 8.09 (dd, J=8.7, 2.2 Hz, 1H), 8.01 (s, 1H), 7.82 (d, J=8.6 Hz, 1H), 7.55-7.61 (m, 2H), 7.36-7.43 (m, 2H), 7.25-7.31 (m, 1H). MS (M+1): 348.0.

Reference： [1]Patent: US2012/202834,2012,A1 .Location in patent: Page/Page column 21

9
[ 59184-90-6 ]
[ 171197-80-1 ]
[ 1388144-27-1 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In N,N-dimethyl-formamide; at 160℃; for 1h;Microwave irradiation;	Step A: Ethyl 1 -(5-iodopyridm-2-yl)piperidin-4-yl]acetate2-fluoro~5-iodopyridine (2.2 g, 9.86 mmol, 1.1 equiv.) and ethyl piperidin-4-ylacetate (1.535 g, 8.96 mmol, 1.0 equiv.) were dissolved in DMF (12 mL) and stirred. Cesium carbonate (4.38 g, 13.45 mmol, 1.5 equiv.) was added to the solution, and the resulting reaction suspension was reacted under microwave conditions (160C, Ihr). After cooling to room temperature, the reaction suspension was filtered to remove solids. The collected solution was concentrated to a residue. Purification with SP-1 Biotage [ Hexanes:EtOAc 0 > 5% 2CV 5 > 40% 10CV 40% 2CV ] isolated the desired product Ethyl [l-(5-iodopyridin-2-yl)piperidm-4-yl]acetate. LC-MS (ES, m/z): C1 H19IN2O2: 374; Found: 375 [M+H]+.

Reference： [1]Patent: WO2012/96813,2012,A1 .Location in patent: Page/Page column 47

10
[ 1160247-92-6 ]
[ 171197-80-1 ]
[ 1432436-53-7 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium In tetrahydrofuran at -78℃; for 0.25h;

Reference： [1]Gentry, Patrick R.; Bridges, Thomas M.; Lamsal, Atin; Vinson, Paige N.; Smith, Emery; Chase, Peter; Hodder, Peter S.; Engers, Julie L.; Niswender, Colleen M.; Scott Daniels; Jeffrey Conn; Wood, Michael R.; Lindsley, Craig W. [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 10, p. 2996 - 3000]

11
[ 171197-80-1 ]
[ 853909-08-7 ]

Reference： [1]Patent: US2014/30191,2014,A1
[2]European Journal of Medicinal Chemistry,2016,vol. 107,p. 153 - 164

12
[ 171197-80-1 ]
[ 663955-59-7 ]

Reference： [1]Patent: US2014/30191,2014,A1
[2]European Journal of Medicinal Chemistry,2016,vol. 107,p. 153 - 164

13
[ 26690-80-2 ]
[ 171197-80-1 ]
tert-butyl N-[2-[(5-iodopyridin-2-yl)oxy]ethyl]carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	Stage #1: 2-fluoro-5-iodopyridine With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.166667h; Stage #2: 2-(N-tert-butoxycarbonylamino)ethanol In N,N-dimethyl-formamide at 0℃; for 0.5h;	25.1 Step-i: Synthesis of tert-butyl (2-((5-iodopyridin-2- yl)oxy)ethyl)carbamate 10433] To a stirred solution of 2-fluoro-5-iodopyridine (5 g, 22.4 mmol) in DMF (25 mE) was added sodium hydride (0.7 g, 33.5 mmol) and stirred for iO mm at 00 C., to the above mixture tert-butyl (2-hydroxyethyl)carbamate (i .8 g, ii .2 mmol) was added. The contents were stirred at 00 C. for 30 mi Afier completion of reaction, reaction mixture was poured onto ice cold water, and extracted with ethyl acetate. The combined organic layers were washed with water followed by saturated NaC1 solution, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude material was purified by column chromatography over 230- 400 mesh silica using i5% EtOAc in n-hexane as an eluent to obtain desired compound tert-butyl (2-((5-iodopyridin-2- yl)oxy)ethyl)carbamate as an off-white solid (3.5 g, 43%)
43%	Stage #1: 2-fluoro-5-iodopyridine With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.166667h; Stage #2: 2-(N-tert-butoxycarbonylamino)ethanol In N,N-dimethyl-formamide at 0℃; for 0.5h;	1m Synthesis of tert-butvl (2-((5-iodopvridin-2-vfloxv’ethvflcarbamate To a stirred solution of 2-fluoro-5-iodopyridine (5 g, 22.4 mmol) in DMF (25 mL) was added sodium hydride (0.7 g, 33.5 mmol) and stirred for 10 mm at 0°C, to the above mixture tert-butyl (2-hydroxyethyl)carbamate (1.8 g, 11.2 mmol) was added. The contents were stirred at 0°C for 30 mm. After completion of reaction, reaction mixture was poured onto ice cold water, and extracted with ethyl acetate. The combined organic layers were washed with water followed by saturated NaC1 solution, dried over anhydrous Na2504 and concentrated under reduced pressure. The crude material was purified by column chromatography over 230-400 mesh silica using 15% EtOAc in n-hexane as an eluent to obtain the desired compound tert-butyl (2-((5-iodopyridin-2-yl)oxy)ethyl)carbamate as an off-white solid (3.5 g, 43%).
37%	With caesium carbonate In N,N-dimethyl-formamide at 100℃; for 8h;	101.6 Synthesis of tert-butyl N-f2-f(5-iodopyridiii-2-voxvJethylJcarbamate into a I 00-niL round-bottom flask, was placed 2-fluoro-5-iodopyridine (5 g, 22.42mmoi, 1.00 equiv), tert-hutyl N-(2-hydroxvethyi)carbamaie (5.4 g, 33.SOmmoi, 1.50 equiv), Cs2CO3 (13 g. 3.00 equiv), N,N-dimethyiforrnarnicle (3OinL). The resulting solution was stirred for 8 h at 100°C in an oil bath. Then the reaction mixture was poured into ice cold water, the solid was filtered and dried under reduced pressure to obtain 3,0 g (37%) of tertbutyl N-[2-[(5-iodopvridin-2-yi)oxy] ethyl] carbamate as a white solid

301 g	Stage #1: 2-fluoro-5-iodopyridine With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.166667h; Stage #2: 2-(N-tert-butoxycarbonylamino)ethanol In N,N-dimethyl-formamide at 0 - 20℃; for 8h;	3.1 Step-1: Synthesis of tert-butyl (2-((5-iodopyridin-2-yl)oxy)ethyl)carbamate Step-1: Synthesis of tert-butyl (2-((5-iodopyridin-2-yl)oxy)ethyl)carbamate To a stirred solution of 2-fluoro-5-iodopyridine (250 g, 1.12 mmol) in DMF (2.5 L) was added sodium hydride (67.2 g, 1.68 mol), and the solution was stirred for 10 min at 0° C. Then, tert-butyl (2-hydroxyethyl)carbamate (180.4 g, 1.12 mol) was added. The contents were stirred at R.T. until completion. The reaction mixture was poured onto ice cold water, the solid separated was filtered and dried under reduced pressure to deliver the title compound in 301 g as an off-white solid.
	With sodium hydride; N,N-dimethyl-formamide at 0℃; for 24h;

Reference： [1]Current Patent Assignee: EISAI CO LTD - US2016/347717, 2016, A1 Location in patent: Paragraph 0432; 0433
[2]Current Patent Assignee: EISAI CO LTD - WO2018/97273, 2018, A1 Location in patent: Paragraph 0070
[3]Current Patent Assignee: EISAI CO LTD - WO2018/98251, 2018, A1 Location in patent: Page/Page column 47; 50
[4]Current Patent Assignee: EISAI CO LTD - US2018/141913, 2018, A1 Location in patent: Paragraph 0246; 0247
[5]Current Patent Assignee: DUNAD THERAPEUTICS; 2692372 ONTARIO - WO2021/99842, 2021, A1 Location in patent: Paragraph 00213

14
[ 37663-46-0 ]
[ 171197-80-1 ]
C₁₇H₁₅IN₂O₂ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 3594 - 3605

15
[ 3445-11-2 ]
[ 171197-80-1 ]
1-(2-((5-iodopyridin-2-yl)oxy)ethyl)pyrrolidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With sodium hydride; In N,N-dimethyl-formamide; at 0 - 25℃;	Step-a: Synthesis of 1-(2-((5-iodopyridin-2-yl)oxy)ethyl)pyrrolidin-2-one Into a 250-mL round-bottom flask was placed 1-(2-hydroxyethyl)pyrrolidin-2-one (8.6 g, 66.59 mmol, 1.00 equiv), N,N-dimethylformamide (50 mL), and sodium hydride (1.1 g, 45.83 mmol, 1.20 equiv). The resulting solution was stirred at 0 C. in a water/ice bath until completion. 2-fluoro-5-iodopyridine (5 g, 22.42 mmol, 1.00 equiv) was then added. The resulting solution was allowed to react, with stirring, at 25 C. until completion. The solution was diluted with H2O (100 mL), extracted with 3*100 mL of ethyl acetate, dried over Na2SO4 and the organic layers combined. The crude product was purified by Flash-Prep-HPLC with the following conditions (IntelFlash-1): Column, silica gel; mobile phase, ethyl acetate/petroleum ether (1:9); Detector, UV 254 nm to deliver the title compound in 5.0 g (67%) as light yellow oil. 1H NMR (400 MHz, Methanol-d4) delta 8.34 (dd, J=2.4, 0.7 Hz, 1H), 7.94-7.91 (dd, J=8.7, 2.4 Hz, 1H), 6.69-6.67 (dd, J=8.7, 0.7 Hz, 1H), 4.46-4.43 (m, 2H), 3.68-3.65 (t, J=5.3 Hz, 2H), 3.60-3.56 (m, 2H), 2.382.34 (t, J=8.1 Hz, 2H), 2.07-2.00 (m, 2H). LCMS: 333 [M+H]+.

Reference： [1]Patent: US2018/141913,2018,A1 .Location in patent: Paragraph 0325; 0326

16
[ 1251010-45-3 ]
[ 171197-80-1 ]
[ 2242425-22-3 ]

Yield	Reaction Conditions	Operation in experiment
62.3%	With sodium carbonate In 1-methyl-pyrrolidin-2-one at 85℃;	Synthesis of tert-butyl 7-(5-iodopyridin-2-yl)-3-oxa-7,9-diazabicyclo j3.3. 11 nonane-9-carboxylate (S la). A solution of tert-butyl 3-oxa-7,9-diazabicyclo [3.3.1 jnonane-9-carboxylate(1 g, 4.38 mmol) 2-fluoro-5-iodopyridine (1.12 g, 5.04 mmol), and sodium carbonate (0.84 g,7.88 mmol) in 1-Methyl-2-pyrrolidinone (4 ml) was heated at 85 °C overnight. The mixture wascooled to room temperature, diluted with water and extracted into DCM. The organic extract was dried over Na2SO4 filtered and concentrated under reduced pressure. The residue waspurified by silica chromatography to yield Sia (1.57 g, 62.3%). MS (ESI) mlz 431.9 [M+Hj . 1HNMR (400 MHz, Chloroform-d) ö 8.30 (dd, J = 2.4, 0.7 Hz, 1H), 7.66 (dd, J = 9.0, 2.3 Hz, 1H), 6.44 (d, J = 9.0 Hz, 1H), 4.25 (d, J = 12.7 Hz, 1H), 4.21 - 4.00 (m, 3H), 3.97 - 3.86 (m,2H), 3.80 (t, J= 11.9 Hz, 2H), 3.26 (t, J= 15.1 Hz, 2H), 1.48 (s, 9H).
62.3%	With sodium carbonate In 1-methyl-pyrrolidin-2-one at 85℃;	1.2 Synthesis of tert-butyl 7-(5-iodopyridin-2-yl)-3-oxa-7,9-diazabicyclo[3.3.1]nonane-9-carboxylate (S1a) A solution of tert-butyl 3-oxa-7,9-diazabicyclo[3.3.1]nonane-9-carboxylate (1 g, 4.38 mmol) 2-fluoro-5-iodopyridine (1.12 g, 5.04 mmol), and sodium carbonate (0.84 g, 7.88 mmol) in 1-methyl-2-pyrrolidinone (4 mL) was heated at 85° C. overnight. The mixture was cooled to room temperature, diluted with water and extracted into DCM. The organic extract was dried over Na2SO4 filtered and concentrated under reduced pressure. The residue was purified by silica chromatography to yield S1a (1.57 g, 62.3%). MS (ESI) m/z 431.9 [M+H]+. 1H NMR (400 MHz, Chloroform-d) δ 8.30 (dd, J=2.4, 0.7 Hz, 1H), 7.66 (dd, J=9.0, 2.3 Hz, 1H), 6.44 (d, J=9.0 Hz, 1H), 4.25 (d, J=12.7 Hz, 1H), 4.21-4.00 (m, 3H), 3.97-3.86 (m, 2H), 3.80 (t, J=11.9 Hz, 2H), 3.26 (t, J=15.1 Hz, 2H), 1.48 (s, 9H).

Reference： [1]Current Patent Assignee: GILEAD SCIENCES INC - WO2018/145021, 2018, A1 Location in patent: Page/Page column 90; 91
[2]Current Patent Assignee: GILEAD SCIENCES INC - US2020/30327, 2020, A1 Location in patent: Paragraph 0348; 0349

17
[ 109384-27-2 ]
[ 171197-80-1 ]
4-(5-iodopyridin-2-yl)-1-methylpiperazin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In 1-methyl-pyrrolidin-2-one; at 85℃;	General procedure: A solution of tert-butyl 3-oxa-7,9-diazabicyclo [3.3.1 jnonane-9-carboxylate(1 g, 4.38 mmol) 2-fluoro-5-iodopyridine (1.12 g, 5.04 mmol), and sodium carbonate (0.84 g,7.88 mmol) in 1-Methyl-2-pyrrolidinone (4 ml) was heated at 85 C overnight. The mixture wascooled to room temperature, diluted with water and extracted into DCM. The organic extract was dried over Na2SO4 filtered and concentrated under reduced pressure. The residue waspurified by silica chromatography to yield Sia (1.57 g, 62.3%). MS (ESI) mlz 431.9 [M+Hj . 1HNMR (400 MHz, Chloroform-d) oe 8.30 (dd, J = 2.4, 0.7 Hz, 1H), 7.66 (dd, J = 9.0, 2.3 Hz, 1H), 6.44 (d, J = 9.0 Hz, 1H), 4.25 (d, J = 12.7 Hz, 1H), 4.21 - 4.00 (m, 3H), 3.97 - 3.86 (m,2H), 3.80 (t, J= 11.9 Hz, 2H), 3.26 (t, J= 15.1 Hz, 2H), 1.48 (s, 9H).

Reference： [1]Patent: WO2018/145021,2018,A1 .Location in patent: Page/Page column 90; 91; 120

18
[ 17768-41-1 ]
[ 171197-80-1 ]
N-(1-adamantylmethyl)-6-fluoropyridin-3-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With copper(l) iodide; 2-(2-methyl-1-oxopropyl)cyclohexanone; caesium carbonate; In N,N-dimethyl-formamide; at 140℃; for 24h;Inert atmosphere;	General procedure: A dry vial with a screwcap equipped with a magnetic stirrer was filled with dry argon, charged with CuI(10-20 mol%, 10-20 mg), ligand L1 or L2, 20-40 mol%, 2-fluoro-5-iodopyridine (0.5 mmol, 112 mg),DMF (1 mL) and adamantylalkyl amine (0.5 mmol) in stream of dry argon. The reaction mixture wasstirred for 1 min, then cesium carbonate (1 mmol, 326 mg) was added and the reaction was stirred at140 C or 110 C. After ca. 24 h the mixture was cooled down to ambient temperature, CH2Cl2 (5 mL)was added, the organic solution was filtered, the residue was washed additionally with CH2Cl2 (2 × 5 mL),the combined organic fractions were evaporated in vacuo. To obtain individual compounds, the residuewas chromatographed on silica gel using a sequence of eluents: petroleum ether, petroleum ether(PE)/CH2Cl2 (2:1, 1:1, 1:2 v/v), CH2Cl2, CH2Cl2/MeOH (200:1, 100:1, 50:1, 33:1; 25:1 v/v).Catalyst-free amination was carried out according to the same procedure without adding catalyst andusing dry K2CO3 (4 equiv., 2 mmol) instead of Cs2CO3.

Reference： [1]Heterocycles,2019,vol. 99,p. 1342 - 1354

19
[ 17768-41-1 ]
[ 171197-80-1 ]
N-(1-adamantylmethyl)-5-iodopyridin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With potassium carbonate; In N,N-dimethyl-formamide; at 140℃; for 24h;Inert atmosphere;	General procedure: A dry vial with a screwcap equipped with a magnetic stirrer was filled with dry argon, charged with CuI(10-20 mol%, 10-20 mg), ligand L1 or L2, 20-40 mol%, 2-fluoro-5-iodopyridine (0.5 mmol, 112 mg),DMF (1 mL) and adamantylalkyl amine (0.5 mmol) in stream of dry argon. The reaction mixture wasstirred for 1 min, then cesium carbonate (1 mmol, 326 mg) was added and the reaction was stirred at140 C or 110 C. After ca. 24 h the mixture was cooled down to ambient temperature, CH2Cl2 (5 mL)was added, the organic solution was filtered, the residue was washed additionally with CH2Cl2 (2 × 5 mL),the combined organic fractions were evaporated in vacuo. To obtain individual compounds, the residuewas chromatographed on silica gel using a sequence of eluents: petroleum ether, petroleum ether(PE)/CH2Cl2 (2:1, 1:1, 1:2 v/v), CH2Cl2, CH2Cl2/MeOH (200:1, 100:1, 50:1, 33:1; 25:1 v/v).Catalyst-free amination was carried out according to the same procedure without adding catalyst andusing dry K2CO3 (4 equiv., 2 mmol) instead of Cs2CO3.

Reference： [1]Heterocycles,2019,vol. 99,p. 1342 - 1354

20
[ 3019-25-8 ]
[ 171197-80-1 ]
1-((1R,2S)-2-(6-fluoropyridin-3-yl)cyclobutyl)ethan-1-one [ No CAS ]
1-(2-(6-fluoropyridin-3-yl)cyclobutyl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88 % ee	With silver orthophosphate; D-Val-OH; palladium diacetate; trifluoroacetic acid; 3-nitro-5-trifluoromethylpyridin-2-ol at 100℃; for 24h; Microwave irradiation; Sealed tube; Overall yield = 37 percent; Overall yield = 7.1 mg; enantioselective reaction;

Reference： [1]Ewing, William R.; Hong, Kai; Hu, Liang; Luo, Fan; Xiao, Li-Jun; Yeung, Kap-Sun; Yu, Jin-Quan [Angewandte Chemie - International Edition, 2020, vol. 59, # 24, p. 9594 - 9600][Angew. Chem., 2020, vol. 132, # 24, p. 9681 - 9687,7]

21
[ 171197-80-1 ]
[ 421595-81-5 ]
C₁₂H₉IN₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
8.8%	With caesium carbonate In N,N-dimethyl-formamide at 120℃; for 15h;	1 Preparation of compound 6 A suspension of 2-fluoro-5-iodopyridine (112 mg, 0.5 mmol), compound 2 (66.5 mg, 0.5 mmol) and cesium carbonate in DMF (4 mL) was stirred at 120 ° C. for 15 hours. .. The reaction mixture was allowed to cool to room temperature, water was added, and the mixture was extracted with ethyl acetate. After washing with water, the extract was dried over magnesium sulfate, filtered, and the filtrate was evaporated under reduced pressure. The obtained residue was purified by flash chromatography (silica gel, elution solvent: chloroform / methanol 9/1), and the solvent was distilled off under reduced pressure to obtain compound 6 (14.7 mg, 0.04) as a white-yellow solid. mmol, 8.8%) was obtained.

Reference： [1]Current Patent Assignee: CLINO - JP2021/102593, 2021, A Location in patent: Paragraph 0085; 0100-0101

22
[ 107017-73-2 ]
[ 171197-80-1 ]
tert-butyl (1-(((5-iodopyridin-2-yl)oxy)methyl)cyclopropyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With sodium hydride In N,N-dimethyl-formamide at 20 - 30℃; for 2h; Inert atmosphere;	1.1 Tert-butyl (1-(((5-iodopyridin-2-yl)oxy)methyl)cyclopropyl)carbamate 1c Sodium hydride (0.4 g, 10.7 mmol) was dissolved in N,N-dimethylformamide (20 mL), followed by the addition of tert-butyl (1-(hydroxymethyl)cyclopropyl)carbamate 1b (1.0 g, 5.3 mmol, prepared according to the method disclosed in "") at room temperature. After completion of the addition, 2-fluoro-5-iodopyridine 1a (1.8 g, 8.0 mmol) was added slowly. The reaction was stirred at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure, and the resulting residues were purified by thin layer chromatography with developing system B to obtain the title product 1c (2.4 g, yield: 86%). MS m/z(ESI): 391.0 [M+1].
86%	With sodium hydride In N,N-dimethyl-formamide at 20 - 30℃; for 2h; Inert atmosphere;	1.1 Tert-butyl (1-(((5-iodopyridin-2-yl)oxy)methyl)cyclopropyl)carbamate 1c Sodium hydride (0.4 g, 10.7 mmol) was dissolved in N,N-dimethylformamide (20 mL), followed by the addition of tert-butyl (1-(hydroxymethyl)cyclopropyl)carbamate 1b (1.0 g, 5.3 mmol, prepared according to the method disclosed in "") at room temperature. After completion of the addition, 2-fluoro-5-iodopyridine 1a (1.8 g, 8.0 mmol) was added slowly. The reaction was stirred at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure, and the resulting residues were purified by thin layer chromatography with developing system B to obtain the title product 1c (2.4 g, yield: 86%). MS m/z(ESI): 391.0 [M+1].
86%	With sodium hydride In N,N-dimethyl-formamide at 20 - 30℃; for 2h; Inert atmosphere;	1.1 Tert-butyl (1-(((5-iodopyridin-2-yl)oxy)methyl)cyclopropyl)carbamate 1c Sodium hydride (0.4 g, 10.7 mmol) was dissolved in N,N-dimethylformamide (20 mL), followed by the addition of tert-butyl (1-(hydroxymethyl)cyclopropyl)carbamate 1b (1.0 g, 5.3 mmol, prepared according to the method disclosed in "") at room temperature. After completion of the addition, 2-fluoro-5-iodopyridine 1a (1.8 g, 8.0 mmol) was added slowly. The reaction was stirred at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure, and the resulting residues were purified by thin layer chromatography with developing system B to obtain the title product 1c (2.4 g, yield: 86%). MS m/z(ESI): 391.0 [M+1].

Reference： [1]Current Patent Assignee: JIANGSU HENGRUI MEDICINE CO., LTD. - EP3988547, 2022, A1 Location in patent: Paragraph 0108; 0115; 0117-0119
[2]Current Patent Assignee: JIANGSU HENGRUI MEDICINE CO., LTD. - EP3988547, 2022, A1 Location in patent: Paragraph 0108; 0115; 0117-0119
[3]Current Patent Assignee: JIANGSU HENGRUI MEDICINE CO., LTD. - EP3988547, 2022, A1 Location in patent: Paragraph 0108; 0115; 0117-0119

23
[ 10316-79-7 ]
[ 171197-80-1 ]
1-(((5-iodopyridin-2-yl)oxy)methyl)cyclopentan-1-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With potassium-t-butoxide In tetrahydrofuran at 20 - 30℃; for 2h; Inert atmosphere;	7.1 1-(((5-Iodopyridin-2-yl)oxy)methyl)cyclopentan-1-amine 7b Potassium tert-butoxide (0.4 g, 3.5 mmol) was dissolved in tetrahydrofuran (10 mL), followed by the addition of (1-aminocyclopentyl)methanol 7a (0.4 g, 3.5 mmol, prepared according to the method disclosed in "") at room temperature. After completion of the addition, compound 1a (0.8 g, 3.5 mmol) was added slowly. The reaction was stirred at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure, and the resulting residues were purified by thin layer chromatography with developing system B to obtain the title product 7b (0.7 g, yield: 66%). MS m/z(ESI): 319.1 [M+1].
66%	With potassium-t-butoxide In tetrahydrofuran at 20 - 30℃; for 2h; Inert atmosphere;	7.1 1-(((5-Iodopyridin-2-yl)oxy)methyl)cyclopentan-1-amine 7b Potassium tert-butoxide (0.4 g, 3.5 mmol) was dissolved in tetrahydrofuran (10 mL), followed by the addition of (1-aminocyclopentyl)methanol 7a (0.4 g, 3.5 mmol, prepared according to the method disclosed in "") at room temperature. After completion of the addition, compound 1a (0.8 g, 3.5 mmol) was added slowly. The reaction was stirred at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure, and the resulting residues were purified by thin layer chromatography with developing system B to obtain the title product 7b (0.7 g, yield: 66%). MS m/z(ESI): 319.1 [M+1].
66%	With potassium-t-butoxide In tetrahydrofuran at 20 - 30℃; for 2h; Inert atmosphere;	7.1 1-(((5-Iodopyridin-2-yl)oxy)methyl)cyclopentan-1-amine 7b Potassium tert-butoxide (0.4 g, 3.5 mmol) was dissolved in tetrahydrofuran (10 mL), followed by the addition of (1-aminocyclopentyl)methanol 7a (0.4 g, 3.5 mmol, prepared according to the method disclosed in "") at room temperature. After completion of the addition, compound 1a (0.8 g, 3.5 mmol) was added slowly. The reaction was stirred at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure, and the resulting residues were purified by thin layer chromatography with developing system B to obtain the title product 7b (0.7 g, yield: 66%). MS m/z(ESI): 319.1 [M+1].

Reference： [1]Current Patent Assignee: JIANGSU HENGRUI MEDICINE CO., LTD. - EP3988547, 2022, A1 Location in patent: Paragraph 0108; 0115; 0165-0167
[2]Current Patent Assignee: JIANGSU HENGRUI MEDICINE CO., LTD. - EP3988547, 2022, A1 Location in patent: Paragraph 0108; 0115; 0165-0167
[3]Current Patent Assignee: JIANGSU HENGRUI MEDICINE CO., LTD. - EP3988547, 2022, A1 Location in patent: Paragraph 0108; 0115; 0165-0167

Recommend Products

Same Skeleton Products

Related Products

Isomers

Technical Information

• Acid-Catalyzed α -Halogenation of Ketones • Alcohols from Haloalkanes by Acetate Substitution-Hydrolysis • Alcohols React with PX3 • Alkyl Halide Occurrence • An Alkane are Prepared from an Haloalkane • Chichibabin Reaction • Convert Haloalkanes into Alcohols by SN2 • Friedel-Crafts Alkylation of Benzene with Haloalkanes • General Reactivity • Hantzsch Pyridine Synthesis • Hiyama Cross-Coupling Reaction • Kinetics of Alkyl Halides • Methylation of Ammonia • Preparation of Amines • Pyridines React with Grignard or Organolithium Reagents • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Dihalides • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling

Historical Records

Related Functional Groups of
[ 171197-80-1 ]

Fluorinated Building Blocks

[ 1184913-75-4 ]

2-Fluoro-5-iodo-4-methylpyridine

Similarity: 0.86

[ 22282-70-8 ]

2-Fluoro-4-iodopyridine

Similarity: 0.83

[ 851386-35-1 ]

2,3-Difluoro-5-iodopyridine

Similarity: 0.80

[ 372-48-5 ]

2-Fluoropyridine

Similarity: 0.77

[ 153034-94-7 ]

2-Fluoro-4-iodo-5-picoline

Similarity: 0.73

Related Parent Nucleus of
[ 171197-80-1 ]

Pyridines