[ CAS No. 207994-08-9 ] {[proInfo.proName]}

Name: 207994-08-9|5-Chloro-3-fluoropicolinic acid|98%
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Quality Control of [ 207994-08-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 207994-08-9 ]

Product Details of [ 207994-08-9 ]

CAS No. :	207994-08-9	MDL No. :	MFCD12827555
Formula :	C₆H₃ClFNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ISWYPIVHUPCJGU-UHFFFAOYSA-N
M.W :	175.54	Pubchem ID :	11769070
Synonyms :

Calculated chemistry of [ 207994-08-9 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	36.16
TPSA :	50.19 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) :	-6.35 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.01
Log Po/w (XLOGP3) :	1.44
Log Po/w (WLOGP) :	1.99
Log Po/w (MLOGP) :	-0.08
Log Po/w (SILICOS-IT) :	1.82
Consensus Log Po/w :	1.24

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.85

Water Solubility

Log S (ESOL) :	-2.17
Solubility :	1.18 mg/ml ; 0.00671 mol/l
Class :	Soluble
Log S (Ali) :	-2.1
Solubility :	1.4 mg/ml ; 0.00795 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.29
Solubility :	0.898 mg/ml ; 0.00512 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.61

Safety of [ 207994-08-9 ]

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 [ 207994-08-9 ]

* 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 [ 207994-08-9 ]

[ 207994-08-9 ] Synthesis Path-Downstream 1~49

1
[ 124-38-9 ]
[ 514797-97-8 ]
[ 207994-08-9 ]

Reference： [1]European Journal of Organic Chemistry,2002,p. 4174 - 4180

2
[ 124-38-9 ]
[ 514797-98-9 ]
[ 207994-08-9 ]

Reference： [1]European Journal of Organic Chemistry,2002,p. 4174 - 4180

3
[ 89402-43-7 ]
[ 207994-08-9 ]

Reference： [1]European Journal of Organic Chemistry,2002,p. 4174 - 4180
[2]European Journal of Organic Chemistry,2002,p. 4174 - 4180

4
[ 514797-97-8 ]
[ 207994-08-9 ]

Reference： [1]European Journal of Organic Chemistry,2002,p. 4174 - 4180

5
[ 514797-96-7 ]
[ 207994-08-9 ]

Reference： [1]European Journal of Organic Chemistry,2002,p. 4174 - 4180
[2]European Journal of Organic Chemistry,2002,p. 4174 - 4180

6
[ 514798-05-1 ]
[ 207994-08-9 ]

Reference： [1]European Journal of Organic Chemistry,2002,p. 4174 - 4180
[2]European Journal of Organic Chemistry,2002,p. 4174 - 4180

7
[ 514798-06-2 ]
[ 207994-08-9 ]

Reference： [1]European Journal of Organic Chemistry,2002,p. 4174 - 4180

8
[ 207994-08-9 ]
[ 207994-09-0 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; In hexane; toluene;	Example H6 3-Fluoro-5-chloro-2-pyridinecarbonyl chloride 71.38 g of <strong>[207994-08-9]3-fluoro-5-chloro-2-pyridinecarboxylic acid</strong> is initially introduced into a round-bottomed flask and heated up to 90 C. 59 ml of thionyl chloride are added dropwise from a dropping funnel in the course of 30 minutes, and the gas formed is passed into sodium hydroxide solution. The mixture is subsequently stirred at 100 C. for a further 5 hours. The thionyl chloride is then distilled off under normal pressure. After addition of 50 ml of dry toluene, 20 ml thereof are distilled off. The solution thus obtained is poured onto 200 ml of n-hexane and the mixture is stirred overnight. After cooling in an ice-bath, the mixture is filtered and the material on the filter is washed twice with n-hexane. 68.7 9 of the desired compound are obtained as a brown solid. 1H-NMR (CDCl3): 8.60 ppm (d, 1H); 7.69 ppm (dxd, 1H).
	In thionyl chloride; hexane; toluene;	Example P6 3-Fluoro-5-chloro-2-pyridinecarboxylic Acid Chloride 71.38 g of <strong>[207994-08-9]3-fluoro-5-chloro-2-pyridinecarboxylic acid</strong> (Example P4) are placed in a round-bottomed flask and heated to 90 C. 59 ml of thionyl chloride are added dropwise from a dropping funnel over a period of 30 minutes, and the gas formed is introduced into sodium hydroxide solution. Stirring is then carried out for 5 hours at 100 C., after which the thionyl chloride is distilled off at normal pressure. After the addition of 50 ml of dry toluene, 20 ml thereof are distilled off. The resulting solution is poured into 200 ml of n-hexane and stirred overnight. After cooling in an ice-bath, the mixture is filtered and the filtration residue is washed twice with n-hexane. 68.7 g of the desired compound are obtained in the form of a brown solid. 1H-NMR (CDCl3): 8.60 ppm (d, 1H); 7.69 ppm (dxd, 1H).

Reference： [1]Patent: US6204221,2001,B1
[2]Patent: US6274536,2001,B1

9
3-fluoro-5-chloro-2-pyridinecarboxylic acid ethyl ester [ No CAS ]
[ 207994-08-9 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium hydroxide; dimethyl sulfoxide; In ice-water;	Example H4 3-Fluoro-5-chloro-2-pyridinecarboxylic acid 70 g of ethyl 3-fluoro-5-chloro-2-pyridinecarboxylate (Example H1) are initially introduced into 105 ml of dimethyl sulfoxide (DMSO). 230 ml of a 2N sodium hydroxide solution are added dropwise at 40 C. in the course of 30 minutes. The resulting yellow suspension is introduced into a mixture of 2 l of ice-water and 400 ml of 2N hydrochloric acid. After subsequently stirring for 20 minutes, the mixture is filtered and the material on the filter is washed twice with water. 56.4 g of the desired target compound are obtained as a white solid. 1H-NMR (DMSO-D6): 13.79 ppm (broad signal, 1H); 8.60 ppm (d, 1H); 8.27 ppm (dxd, 1H).

Reference： [1]Patent: US6204221,2001,B1

10
[ 207994-08-9 ]
[ 1270977-95-1 ]

Reference： [1]Patent: WO2011/28685,2011,A1

11
[ 207994-08-9 ]
[ 1270977-97-3 ]

Reference： [1]Patent: WO2011/28685,2011,A1

12
4-piperazin-1-yl-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]butanenitrile hydrochloride [ No CAS ]
[ 207994-08-9 ]
C₂₉H₃₅ClFN₉O₂Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of <strong>[207994-08-9]5-chloro-3-fluoropyridine-2-carboxylic acid</strong> (23.5 mg, 0.134 mmol, prepared as described in Eur. J. Org. Chem. (24), 4174-4180; 2002) and triethylamine (86.2 uL, 0.618 mmol) in THF (1.1 mL) was added N,N,N',N'-tetramethyl-0-(7-azabenzotriazol-l- yl)uronium Hexafluorophosphate (47.0 mg, 0.124 mol). After stirring for 15 minutes, 4- piperazin-l-yl-3-[4-(7- [2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)- lH-pyrazol-l-yl]butanenitrile hydrochloride (61 mg, 0.10 mmol; from Example 12, Step 2) was added. The reaction was stirred for two hours. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed successively with water, 0.1 N NaOH and brine, dried over sodium sulfate and concentrated. The residue was stirred in a 1 : 1 mixture of DQVLTFA for 1 hour, concentrated, and stirred in methanol (1 mL) containing ethylenediamine (0.2 mL) for 1 hour. Preparative HPLC-MS, eluting with a gradient of MeCN/H20 containing 0.15% NH4OH, was used to purify the product (29 mg, 57%). XH NMR (300 MHz, d6-dmso): delta 12.10 (br s, 1H), 8.81 (s, 1H), 8.61 (s, 1H), 8.55 (dd, 1H), 8.37 (s, IH), 8.24 (dd, IH), 7.60 (d, IH), 6.97 (d, IH), 4.98 (tt, IH), 3.65-3.56 (m, 2H), 3.26- 3.12 (m, 4H), 2.92-2.77 (m, 2H), 2.64-2.25 (m, 4H); LCMS (M+H)+: 494. 2.

Reference： [1]Patent: WO2011/28685,2011,A1 .Location in patent: Page/Page column 79; 80

13
C₁₃H₁₆FN₃O [ No CAS ]
[ 207994-08-9 ]
[ 1352417-54-9 ]
[ 1352417-55-0 ]

Yield	Reaction Conditions	Operation in experiment
6%; 18%	With 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; In methanol; at 0℃; for 6h;	5-Chloro-3-fluoropyridine-2-carboxylic acid (0.253 g, 1.444 mmol) was dissolved in MeOH (49 mL) and DMTMM (0.461 g, 1.564 mmol) was added. After stirring the mixture for 5 minutes, a solution of a mixture of intermediates 138 and 139 (0.3 g, 0.1.2 mmol) in MeOH (20 mL) was added at 0 C, and the mixture was stirred for an additional 6 h. The solvent was evaporated in vacuo. The crude material was purified by flash column chromatography (silica gel; 7 M solution of ammonia inmethanol/DCM 0/100 to 5/95). The desired fractions of each diastereomer were collected and the solvent evaporated in vacuo to yield compound 249 (0.03 g, 6 % yield) and compound 250 (0.082 g, 18% yield) as solids after precipitation in DIPE

Reference： [1]Patent: WO2011/154431,2011,A1 .Location in patent: Page/Page column 124

14
[ 1369543-83-8 ]
[ 207994-08-9 ]
[ 1369542-91-5 ]

Yield	Reaction Conditions	Operation in experiment
73%		Example BIOPreparation of compound 33: (R)-N-(3-r6-amino-4-cvclopropyl-4,7- dihydropyrazolo [ 1 , 5 -alpyrazin-4-yll -4-fluorophenyl I -5 -chloro-3 -fluoropyridine-2- carboxamide5 -Chloro-3 -fluoropyridine-2-carboxylic acid (0.052 g, 0.26 mmol) was dissolved in MeOH (1.5 mL) and DMTMM (0.086 g, 0.31 mmol) was added. After stirring the mixture for 5 minutes, a solution of intermediate 81 (0.074 g, 0.26 mmol) in MeOH (1.5 mL) was added at 0 C, and the mixture was stirred for an additional 24 h. The solvent was evaporated in vacuo. The crude product was purified by flash column chromatography (silica gel; 7 M solution fo ammonia in methanol/DCM 0/100 to 5/95). The desired fractions were collected and concentrated in vacuo. The residue was dried under vacuum to yield compound 33 (0.084 g, 73% yield) as a white solid.
73%		5-Chloro-3-fluoropyridine-2-carboxylic acid (0.052 g, 0.26 mmol) was dissolved in MeOH (1.5 mL) and DMTMM (0.086 g, 0.31 mmol) was added. After stirring the mixture for 5 minutes, a solution of intermediate 81 (0.074 g, 0.26 mmol) in MeOH (1.5 mL) was added at 0 C., and the mixture was stirred for an additional 24 h. The solvent was evaporated in vacuo. The crude product was purified by flash column chromatography (silica gel; 7 M solution of ammonia in methanol/DCM 0/100 to 5/95). The desired fractions were collected and concentrated in vacuo. The residue was dried under vacuum to yield compound 33 (0.084 g, 73% yield) as a white solid.

Reference： [1]Patent: WO2012/38438,2012,A1 .Location in patent: Page/Page column 64
[2]Patent: US2013/190318,2013,A1 .Location in patent: Paragraph 0247; 0248

15
[ 207994-08-9 ]
[ 543-27-1 ]
C₁₁H₁₁ClFNO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; at -25 - -15℃; for 0.333333h;	5-chloro-2-chloromethyl-3-fluoro-pyridine hydrochloride; [00379] To a - 15C solution of <strong>[207994-08-9]5-chloro-3-fluoropyridine-2-carboxylic acid</strong> (4.80 g, 27.3 mmol) in tetrahydrofuran (96 mL) was added isobutyl chloroformate (3.73 g, 27.34 mmol), dropwise, followed by triethylamine (3.80 mL, 27.3 mmol), resulting in a tan suspension. This reaction mixture was stirred at -25C for 20 minutes, after which the solids were removed by filtration. The remaining filtrate was cooled 0C, after which a solution of sodium borohydride (1.55 g, 40.1 mmol) in water (15 mL) was added, and the resulting reaction mixture was warmed to room temperature and stirred for 18 hours, then diluted with water (100 mL), adjusted to pH~7 with 2 mL of a 10% hydrochloric acid solution, extracted with ethyl acetate (2 x 80 mL), dried (sodium sulfate), filtered and concentrated. Purification was achieved by silica gel chromatography using 0.5% methanol in dichloromethane to afford (5-chloro-3-fluoro-pyridin-2-yl)-methanol (2.33 g, 14.4 mmol, 53.0 %) as a white solid.[00380] To a room temperature solution of (5-chloro-3-fluoro-pyridin-2-yl)-methanol (1.87 g, 11.6 mmol) in dichloromethane (19 mL) was added thionyl chloride (2.80 mL, 38.6 mmol), and the resulting suspension was refluxed for one hour. The reaction mixture was then concentrated, and the resulting residue was triturated with diethyl ether afford 5-chloro- 2-chloromethyl-3-fluoro-pyridine hydrochloride as a tan solid (1.70 g, 7.85 mmol, 68% yield). NMR (400 MHz, CDC13) delta (ppm): 8.41 (s, 1H), 7.51 (d, 1H), 4.71 (s, 2H).

Reference： [1]Patent: WO2012/88469,2012,A1 .Location in patent: Page/Page column 154-155

16
[ 207994-08-9 ]
[ 1383924-64-8 ]

Reference： [1]Patent: WO2012/88469,2012,A1

17
[ 207994-08-9 ]
[ 214055-12-6 ]

Yield	Reaction Conditions	Operation in experiment
1.88 g		(1) To a suspension of the Compound 1 (5.21 g) in 1,2- dimethoxyethane (30 mE) were added isobutyl chloroformate (4.24 mE) and N-methylmorpholine (3.6 mE) under ice-cooling, and the resulting mixture was stirred at the same temperature for 1 hout The resulting insoluble matters were removed by filtration, and to the resulting filtrate was added an aqueous solution of sodium borohydride (sodium borohydride (1.69 g)+water (15 mE)) under ice-cooling, and the resulting mixture was stirred at room temperature for 2 hours. To the reaction mixture were added water and chloroform, and the resulting mixture was stirred, and then extracted with chloroform. The resulting organic layers were dried, and then concentrated under reduced pressure. The resulting residues were purified by NH silica gel column chromatography (hexane:ethyl acetate=95:5 to 65:35) to give the Compound 2 (1.88 g) as a colorless solid. MS (APCI): mlz 162/164 [M+H]
1.88 g	With 4-methyl-morpholine; isobutyl chloroformate; In 1,2-dimethoxyethane; for 1h;Cooling with ice;	(1) Compound 1 (5.21 g)Of 1, 2-dimethoxyethane (30 mL)Isobutyl chloroformate (4.24 mL) was added to the suspension under ice cooling,And N-methylmorpholine(3.6 mL)Is added,The mixture was stirred at the same temperature for 1 hour.Insolubles were removed by filtration,To the filtrate was added sodium borohydride aqueous solution(Sodium borohydride 1.69 g + water 15 mL)Is added,And the mixture was stirred at room temperature for 2 hours.Water and chloroform were added to the reaction mixture, followed by stirring,And extracted with chloroform.The obtained organic layer was dried and concentrated under reduced pressure.The residue was purified by NH silica gel column chromatography (hexane: ethyl acetatePurity: 95: 5 to 65: 35)Compound 2 (1.88 g) was obtained as a colorless solid.

Reference： [1]Patent: WO2012/88469,2012,A1
[2]Patent: WO2015/75023,2015,A1
[3]Patent: WO2016/177690,2016,A1
[4]Patent: US2018/258076,2018,A1 .Location in patent: Paragraph 0469
[5]Patent: JP2018/199673,2018,A .Location in patent: Paragraph 0147

18
[ 6638-79-5 ]
[ 2592-95-2 ]
[ 25952-53-8 ]
[ 207994-08-9 ]
[ 1600511-96-3 ]

Yield	Reaction Conditions	Operation in experiment
	With triethanolamine; In n-heptane; dichloromethane;	Step 1: 5-Chloro-3-fluoro-N-methoxy-N-methylpicolinamide To a stirred mixture of <strong>[207994-08-9]5-chloro-3-fluoropicolinic acid</strong> (3.62 g, 20.62 mmol) in dichloromethane (50 mL) were added 1H-benzo[d][1,2,3]triazol-1-ol (0.42 g, 3.09 mmol), N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine HCl (5.93 g, 30.9 mmol), N,O-dimethylhydroxylamine HCl (3.02 g, 30.9 mmol), and TEA (7.19 mL, 51.6 mmol). The reaction mixture was stirred at RT for 2 hours, and then partitioned between ethyl acetate and water. The aqueous layer was extracted with EtOAc, and the combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by column chromatography, eluting with 0-100% EtOAc in heptane, to provide the title intermediate (3.71 g) as a white solid.

Reference： [1]Patent: US2014/107109,2014,A1 .Location in patent: Page/Page column

19
[ 207994-08-9 ]
5-chloro-3-fluoropicolinaldehyde [ No CAS ]

Reference： [1]Patent: US2014/107109,2014,A1
[2]Patent: US2018/258076,2018,A1
[3]Patent: JP2018/199673,2018,A

20
[ 207994-08-9 ]
[ 1600511-91-8 ]