[ CAS No. 1065267-14-2 ] {[proInfo.proName]}

Name: 1065267-14-2|(3,5-Difluoropyridin-2-yl)methanol|98%
Brand: Ambeed
SKU: A489717
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Quality Control of [ 1065267-14-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1065267-14-2 ]

Product Details of [ 1065267-14-2 ]

CAS No. :	1065267-14-2	MDL No. :	MFCD11520700
Formula :	C₆H₅F₂NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XYNXXKCNVYDIET-UHFFFAOYSA-N
M.W :	145.11	Pubchem ID :	53414314
Synonyms :

Calculated chemistry of [ 1065267-14-2 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.17
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	30.28
TPSA :	33.12 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) :	-7.04 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.39
Log Po/w (XLOGP3) :	0.2
Log Po/w (WLOGP) :	1.54
Log Po/w (MLOGP) :	0.75
Log Po/w (SILICOS-IT) :	2.05
Consensus Log Po/w :	1.19

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.24
Solubility :	8.28 mg/ml ; 0.0571 mol/l
Class :	Very soluble
Log S (Ali) :	-0.45
Solubility :	51.0 mg/ml ; 0.351 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.39
Solubility :	0.591 mg/ml ; 0.00407 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.58

Safety of [ 1065267-14-2 ]

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 [ 1065267-14-2 ]

* 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 [ 1065267-14-2 ]

[ 1065267-14-2 ] Synthesis Path-Downstream 1~24

1
[ 1065267-10-8 ]
[ 1065267-14-2 ]

Yield	Reaction Conditions	Operation in experiment
98%	With sodium tetrahydroborate; In ethanol; at 0 - 20℃; for 2h;Cooling with ice;	Step B: Preparation of (3,5-difluoro-pyridin-2-yl)-methanol To a solution of 3,5-difluoro-pyridine-2-carboxylic acid ethyl ester of Step A (2.5 g, 12.6 mmol) in ethanol (10 mL), cooled using an ice water bath, was added sodium borohydride (1.43 g, 37.8 mmol) in a portion wise manner. The solution was stirred at 0 C. for thirty minutes and at ambient temperature for two hours. The reaction was returned to 0 C. and saturated ammonium chloride was added dropwise. The solvent was removed in vacuo and the resulting residue was partitioned between ethyl acetate and water. The organic layer was washed with saturated ammonium chloride, water and brine and dried over magnesium sulfate. The slurry was filtered and concentrated to provide the alcohol as a yellow oil (1.8 g, 98%). MS (M+H): 146
71%	With lithium borohydride; In tetrahydrofuran; at 0 - 25℃;	A stirred solution of ethyl 3,5-difluoropyridine-2-carboxylate (Intermediate 29, 3.1g, 16.57mmol) in anhydrous THF (10OmL) was cooled to O0C. To this solution was added portion- wise LiBH4 (l.lg, 50mmol) under a nitrogen atmosphere. After stirring 30 minutes at O0C, the reaction mixture was warmed to room temperature and stirred overnight. After cooling to O0C, the reaction mixture was quenched with MeOH, followed by saturated NH4Cl (aq) solution. After most of the organic solvent was removed by evaporation, the residue remaining was diluted with H2O and extracted with EtOAc (2x). The combined organic phases were dried (Na2SO4) and evaporated to give the title compound (1.7g, 71%). <n="75"/>LCMS: [M+H]+ 146.

Reference： [1]Patent: US2013/143906,2013,A1 .Location in patent: Paragraph 0316
[2]Patent: WO2008/117050,2008,A1 .Location in patent: Page/Page column 73-74

2
[ 1065267-14-2 ]
[ 780801-58-3 ]

Yield	Reaction Conditions	Operation in experiment
80%	With Dess-Martin periodane; In dichloromethane; at 18 - 25℃;	To a stirred solution of 3,5-difluoropyridin-2-yl)methanol (Intermediate 30, 1.7g, 11.72mmol) in DCM (10OmL) was added Dess-Martin periodinane (DMP) (8.45g, 19.92mmol). The resulting solution was stirred at room temperature overnight under a nitrogen atmosphere. The reaction mixture was diluted with DCM, and washed with saturated NaHCU3 (2x), H2O and brine. The organic layer was dried over Na2SO4, and concentrated. Purification by column chromatography (EtOAc:Hexane = 2:8) provided the title compound (1.4g, 80%) as a thick oil. LCMS: [M+H]+144

Reference： [1]Patent: WO2008/117050,2008,A1 .Location in patent: Page/Page column 74

3
[ 1065267-14-2 ]
[ 1160938-20-4 ]
[ 1160938-47-5 ]

Yield	Reaction Conditions	Operation in experiment
45%	With di-tert-butyl (E)-azodicarboxylate; triphenylphosphine; In dichloromethane; at 25℃; for 2h;	A mixture of 6'-[3-(dimethylamino)-1-pyrrolidinyl]-4-hydroxy-2/-/-1 ,3'-bipyridin-2-one (102 mg, 0.340 mmol) and triphenylphosphine (223 mg, 0.849 mmol) was treated with <strong>[1065267-14-2](3,5-difluoro-2-pyridinyl)methanol</strong> (59.1 mg, 0.408 mmol) dissolved in dichloromethane (3 ml). Bis( 1 , 1 -dimethylethyl) (E)-1 ,2-diazenedicarboxylate (195 mg, 0.849 mmol) was added in two portions, and the reaction mixture was stirred at 250C for 2 h then concentrated under a stream of nitrogen. Purification by reverse phase HPLC (1 to 50% gradient) and concentration of the fractions containing product provided a residue. The residue was treated with aqueous NaHCO3 solution and extracted with ethyl acetate. The organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo to give a white solid (65 mg, 45% yield): 1H NMR (400 MHz, CDCI3) delta ppm 8.36 (d, J = 2.4 Hz, 1 H), 8.02 (d, J = 2.4 Hz, 1 H), 7.46 (dd, J = 9.0, 2.6 Hz, 1 H), 7.28-7.21 (m, 1 H), 7.15 (d, J = 7.6 Hz, 1 H), 6.37 (d, J = 9.0 Hz, 1 H), 6.07 (d, J = 2.7 Hz, 1 H), 5.99 (dd, J = 7.6 2.7 Hz, 1 H), 5.15 (s, 2 H), 3.83-3.73 (m, 1 H), 3.64 (t, J = 8.9 Hz, 1 H), 3.40 (dt, J = 10.1 , 6.9 Hz, 1 H), 3.28 (t, J = 9.0 Hz, 1 H), 2.91-2.78 (m, 1 H), 2.32 (s, 6 H), 2.28-2.18 (m, 1 H), 2.02- 1.88 (m, 1 H); ES-LCMS m/z 428 {M+H)+.

Reference： [1]Patent: WO2009/76387,2009,A1 .Location in patent: Page/Page column 57

4
[ 153034-86-7 ]
[ 1065267-14-2 ]
[ 1260240-62-7 ]

Yield	Reaction Conditions	Operation in experiment
47%	With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate; In toluene; at 105℃; for 16h;Inert atmosphere;	(3,5-Difluoropyridin-2-yl)methanol (4.15 g, 28.4 mmol), 2-chloro-4-iodopyridine (7.47 g, 31.2 mmol), cesium carbonate (12.0 g, 36.3 mmol), CuI (5.40 g, 28.4 mmol) and 1,10-phenanthroline (1.02 g, 5.60 mmol) were stirred in toluene (20 mL) and degassed with a nitrogen stream for 10 minutes. The mixture was heated to 105 C. for 16 h, allowed cool and filtered through a silica plug eluting with ethyl acetate. The filtrate was concentrated, and the residue was purified by column chromatography (80 g ISCO column eluting with ethyl acetate/hexanes; gradient 100% hexanes to 60% ethyl acetate) to provide the title compound (3.42 g, 47%) as a yellow oil: ESI MS m/z 257 [M+H]+.
47%	With 1,10-Phenanthroline; caesium carbonate;copper(l) iodide; In toluene; at 105℃; for 16h;	a) 2((2-Chloropyridin-4-yloxy)methyl)-3,5-difluoropyridine (3,5-Difluoropyridin-2-yl)methanol (4.15 g, 28.4 mmol), 2-chloro-4-iodopyridine (7.47 g, 31.2 mmol), cesium carbonate (12.0 g, 36.3 mmol), CuI (5.40 g, 28.4 mmol) and 1,10-phenanthroline (1.02 g, 5.60 mmol) were stirred in toluene (20 mL) and purged with a nitrogen stream for 10 minutes. The mixture was heated to 105 C. for 16 h, allowed cool and filtered through a silica plug eluding with ethyl acetate. The filtrate was concentrated, and the residue was purified by column chromatography (80 g ISCO column column eluding with ethyl acetate/hexanes; gradient 100% hexanes to 60% ethyl acetate) to yield the title compound (3.42 g, 47%) as a yellow oil; ESI MS m/z 257 [M+H]+.

Reference： [1]Patent: US2011/3738,2011,A1 .Location in patent: Page/Page column 49-50
[2]Patent: US2011/3793,2011,A1 .Location in patent: Page/Page column 107

5
[ 153034-86-7 ]
[ 1065267-14-2 ]
[ 1260240-63-8 ]

Reference： [1]Patent: US2011/3793,2011,A1

6
[ 1065267-14-2 ]
[ 124-63-0 ]
[ 1372891-54-7 ]

Yield	Reaction Conditions	Operation in experiment
78%	With triethylamine; In dichloromethane; at 0℃; for 1.5h;	Intermediate 18: (3,5-difluoro-2-pyridinyl)methyl methanesulfonate; Intermediate 9 <strong>[1065267-14-2](3,5-difluoro-2-pyridinyl)methanol</strong> (114 mg, 0.786 mmol) was dissolved in DCM (anh) (6 mL) at 0C. N, /V-diethylethanamine (ALDRICH, 0.131 mL, 0.943 mmol) and methanesulfonyl chloride (ALDRICH, 0.067 mL, 0.864 mmol) were added. Reaction mixture was stirred at 0C for 1 h 30 min. Crude of reaction was partitioned between water and DCM, aqueous layer was extracted with DCM (2x10 mL). Organic layers were dried over MgS04 (anh) and filtered. Solvent was eliminated to yield title compound (3,5- difluoro-2-pyridinyl)methyl methanesulfonate (137 mg, 0.614 mmol, 78% yield). 1 H NMR (400 MHz, DMSO-de) delta ppm: 1 H NMR (300 MHz, DMSO-cf6) delta ppm: 8.58 (d, 1 H), 8.06-8.1 1 (m, 1 H), 5.36 (d, 2H), 3.27 (s, 3H). [ES+ MS] m/z 224 (MH+).
78%	With diethylamine; In dichloromethane; at 0℃; for 1.5h;	Intermediate 18: (3,5-difluoro-2-pyridinyl)methyl methanesulfonate Intermediate 9 <strong>[1065267-14-2](3,5-difluoro-2-pyridinyl)methanol</strong> (114 mg, 0.786 mmol) was dissolved in DCM (anh) (6 mL) at 0 C. N,N-diethylethanamine (ALDRICH, 0.131 mL, 0.943 mmol) and methanesulfonyl chloride (ALDRICH, 0.067 mL, 0.864 mmol) were added. Reaction mixture was stirred at 0 C. for 1 h 30 min. Crude of reaction was partitioned between water and DCM, aqueous layer was extracted with DCM (2*10 mL). Organic layers were dried over MgSO4 (anh) and filtered. Solvent was eliminated to yield title compound (3,5-difluoro-2-pyridinyl)methyl methanesulfonate (137 mg, 0.614 mmol, 78% yield). 1H NMR (400 MHz, DMSO-d6) delta ppm: 1H NMR (300 MHz, DMSO-d6) delta ppm: 8.58 (d, 1H), 8.06-8.11 (m, 1H), 5.36 (d, 2H), 3.27 (s, 3H). [ES+MS] m/z 224 (MH+). Intermediates 19-21 were prepared by methods analogous to that described for Intermediate 18 but replacing the alcohol (<strong>[1065267-14-2](3,5-difluoro-2-pyridinyl)methanol</strong>) with that indicated in Table 2. Reaction times varied from 1 h to 4 h.
	With triethylamine; In dichloromethane; for 1.5h;Cooling with ice;	In an ice bath, a flask was charged with Dichloromethane (1 mL), (3,5-d ifluoropyridin-2- yl)methanol (200 mg, 1 .378 mmol, commercial source: Rennothech-China, triethylamine (229 muIota_, 1 .654 mmol) and finally methanesulfonyl chloride (1 18 muIota_, 1.516 mmol) that was added dropwise. The crude was left in the same conditions during 1 .5 h. Upon completion, the mixture was partitioned between water and DCM and extracted with DCM (2x). Organic layers were dried over MgS04(anh.) and filtered. Solvent was evaporated under vacuo conditions, obtaining (3,5-difluoropyridin-2-yl)methyl methanesulfonate (205 mg, 0.918 mmol, 66.6%) that was characterized by1H NMR. This crude was used without any purification in the next reaction.1H NMR (400 MHz, CDCI3) delta 8.40 (d, J = 2.5 Hz, 1 H), 7.32-7.27 (m, 1 H), 5.40 (d, J = 2.0 Hz, 2H), 3.1 1 (s, 3H).

Reference： [1]Patent: WO2012/49161,2012,A1 .Location in patent: Page/Page column 32
[2]Patent: US2013/203802,2013,A1 .Location in patent: Paragraph 0255; 0256
[3]Patent: WO2019/34729,2019,A1 .Location in patent: Page/Page column 38; 39

7
[ 745784-04-7 ]
[ 1065267-14-2 ]

Reference： [1]Patent: WO2012/49161,2012,A1
[2]Patent: US2013/143906,2013,A1
[3]Patent: US2013/203802,2013,A1
[4]Patent: WO2015/69512,2015,A1

8
C₁₁H₁₁F₂NO₄ [ No CAS ]
[ 1065267-14-2 ]

Yield	Reaction Conditions	Operation in experiment
42.4%	With sodium tetrahydroborate; water; In tetrahydrofuran; at 0℃; for 0.75h;	Intermediate 9: (3,5-difluoro-2-py; 3,5-difluoro-2-pyridinecarboxylic acid (ALFAAESAR , 300 mg, 1.886 mmol) was dissolved in tetrahydrofuran (THF) (10 mL). A/,A/-diethylethanamine (FLUKA, 0.549 mL, 3.96 mmol) was added and mixture was cooled to -10C (ice in acetone). Isobutyl chloroformate (0.269 mL, 2.074 mmol, FLUKA) was added dropwise. Reaction was stirred 20 min at - 10C. Mixture was filtered into a previously prepared solution of sodium borohydride (ALDRICH, 214 mg, 5.66 mmol) in 2 mL of water at 0C and was stirred at 0C for 45 min. HCI (1 N, aq) was added slowly until neutral pH. Aqueous mixture was partitioned with DCM (3x15ml). Organic layer was dried over Na2S04 (anh), filtered and concentrated. Residue was purified by silica gel chromatography using a linear gradient of DCM/MeOH to yield title compound (3,5-difluoro-2-pyridinyl)methanol (1 16 mg, 0.799 mmol, 42.4% yield). 1 H NMR (400 MHz, DMSO-cfe) delta ppm: 8.44-8.45 (s, 1 H), 7.88-7.93 (m, 1 H), 5.35 (t, 1 H), 4.56-4.58 (m, 2H). [ES+MS] m/z 146 (MH+).
42.4%		Intermediate 9: (3,5-difluoro-2-pyridinyl)methanol 3,5-difluoro-2-pyridinecarboxylic acid (ALFAAESAR, 300 mg, 1.886 mmol) was dissolved in tetrahydrofuran (THF) (10 mL). N,N-diethylethanamine (FLUKA, 0.549 mL, 3.96 mmol) was added and mixture was cooled to -10 C. (ice in acetone). Isobutyl chloroformate (0.269 mL, 2.074 mmol, FLUKA) was added dropwise. Reaction was stirred 20 min at -10 C. Mixture was filtered into a previously prepared solution of sodium borohydride (ALDRICH, 214 mg, 5.66 mmol) in 2 mL of water at 0 C. and was stirred at 0 C. for 45 min. HCl (1N, aq) was added slowly until neutral pH. Aqueous mixture was partitioned with DCM (3*15 ml). Organic layer was dried over Na2SO4 (anh), filtered and concentrated. Residue was purified by silica gel chromatography using a linear gradient of DCM/MeOH to yield title compound (3,5-difluoro-2-pyridinyl)methanol (116 mg, 0.799 mmol, 42.4% yield). 1H NMR (400 MHz, DMSO-d6) delta ppm: 8.44-8.45 (s, 1H), 7.88-7.93 (m, 1H), 5.35 (t, 1H), 4.56-4.58 (m, 2H). [ES+MS] m/z 146 (MH+).

Reference： [1]Patent: WO2012/49161,2012,A1 .Location in patent: Page/Page column 28-29
[2]Patent: US2013/203802,2013,A1 .Location in patent: Paragraph 0242; 0243

9
[ 1065267-14-2 ]
[ 98-59-9 ]
[ 1428987-10-3 ]

Yield	Reaction Conditions	Operation in experiment
35%		(3,5-Difluoropyridin-2-yl)methyl 4-methylbenzenesulfonate (I-5)To a solution of <strong>[1065267-14-2](3,5-difluoropyridin-2-yl)methanol</strong> (0.25 g, 0.7 mmol) in tetrahydrofuran (THF; 10 mL) was added potassium hydroxide (KOH; 0.14 g, 2.55 mmol) at RT, and the mixture was stirred for 15 min p-Toluenesulfonyl chloride (0.42 g, 2.21 mmol) was added slowly at RT, and the reaction mixture was stirred for another 18 h. After complete consumption of the starting material (by TLC), the reaction mixture was diluted with H2O (50 mL) and extracted with EtOAc (2×25 mL). The combined organic extracts were washed with H2O (25 mL) and brine (25 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to obtain the crude material. Purification by silica gel column chromatography eluting with 15% EtOAc/hexane afforded compound I-5 (0.18 g, 0.25 mmol, 35%) as colorless liquid. 1H NMR (500 MHz, CDCl3): delta 8.29 (s, 1H), 7.82 (d, J=8.5 Hz, 2H), 7.34 (d, J=8.5 Hz, 2H), 7.20-7.16 (m, 1H), 5.20 (s, 2H), 2.45 (s, 3H)

Reference： [1]Patent: US2012/329788,2012,A1 .Location in patent: Page/Page column 27-28

10
[ 1065267-14-2 ]
[ 1222633-85-3 ]

Yield	Reaction Conditions	Operation in experiment
87%	With thionyl chloride; N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 1h;Cooling with ice;	Step C: Preparation of 2-chloromethyl-3,5-difluoro-pyridine To a solution of <strong>[1065267-14-2](3,5-difluoro-pyridin-2-yl)-methanol</strong> from Step B (1.8 g, 12.3 mmol) in dichloromethane (20 mL) was added three drops of N,N-dimethylformamide and cooled using an ice water bath. Thionyl chloride (2 mL) was added dropwise and the solution was stirred at ambient temperature for one hour. The solution was concentrated in vacuo to provide the chloro compound as a light brown liquid (1.75 g, 87%).
81%	With thionyl chloride; In dichloromethane; N,N-dimethyl-formamide; for 4h;	Add together <strong>[1065267-14-2](3,5-difluoro-2-pyridyl)methanol</strong> (200 mg, 1.4 mmol), DCM (4 mL), DMF (0.1 mL) and thionyl chloride (1 mL) and stir the mixture for 4 hours. Adjust the pH to about 7.0 with 4 M aqueous sodium bicarbonate and extract the mixture with DCM (3 x 50 mL). Combine the organic portions, dry over anhydrous sodium sulfate, filter, and concentrate to give the title compound (182 mg, 81%) as an orange oil.
1.75 g	With thionyl chloride; N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 1h;Cooling;	Step C: Preparation of 2-chloromethyl-3,5-difluoro-pyridine To a solution of <strong>[1065267-14-2](3,5-difluoro-pyridin-2-yl)-methanol</strong> from part B (1.8 g, 12.3 mmol) in dichloromethane (20 mL) was added three drops of N,N-dimethylformamide and cooled using an ice water bath. Thionyl chloride (2 mL) was added dropwise and the solution was stirred at ambient temperature for one hour. The solution was concentrated in vacuo to provide the chloro compound as a light brown liquid (1.75 g).

Reference： [1]Patent: US2013/143906,2013,A1 .Location in patent: Paragraph 0317
[2]Patent: WO2015/69512,2015,A1 .Location in patent: Page/Page column 19
[3]Patent: US2014/364442,2014,A1 .Location in patent: Paragraph 0135; 0140; 0141

11
[ 1065267-14-2 ]
[ 1442451-89-9 ]

Reference： [1]Patent: US2013/143906,2013,A1

12
[ 1065267-14-2 ]
(+)-5-chloro-6-((3,5-difluoropyridin-2-yl)methoxy)-3-(5-(2-(2-hydroxypropan-2-yl)pyrimidin-4-yl)-2-methylphenyl)-2-methylpyrimidin-4(3H)-one [ No CAS ]
(-)-5-chloro-6-((3,5-difluoropyridin-2-yl)methoxy)-3-(5-(2-(2-hydroxypropan-2-yl)pyrimidin-4-yl)-2-methylphenyl)-2-methylpyrimidin-4(3H)-one [ No CAS ]

Reference： [1]Patent: US2013/143906,2013,A1

13
[ 1065267-14-2 ]
[ 1403745-38-9 ]
[ 1417654-87-5 ]
[ 1417654-88-6 ]

Yield	Reaction Conditions	Operation in experiment
	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; dichloromethane; at 0 - 20℃; for 4h;	Example 37A 3-{1-[(3,5-Difluoropyridin-2-yl)methyl]-5-fluoro-1H-pyrazolo[3,4-b]pyridin-3-yl}-7,7-dimethyl-5-[2-(trimethylsilyl)ethoxy]methyl}-5,7-dihydro-6H-pyrrolo[2,3-e][1,2,4]triazin-6-one [0713] triphenylphosphine were dissolved in 3 ml of tetrahydrofuran and 3 ml dichloromethane, and the mixture was cooled to 0 C. 101 mul (0.524 mmol) of diisopropyl azodicarboxylate were then added, and the solution was stirred at 0 C. for 1 h (solution 1). In a further flask, 0.150 g (0.349 mmol) of the compound from Example 36A and 76 mg (0.542 mmol) of <strong>[1065267-14-2](3,5-difluoropyridin-2-yl)methanol</strong> were dissolved in tetrahydrofuran (6 ml), and the mixture was cooled to 0 C. (solution 2). Solution 1 was then added to this solution 2, and the reaction mixture was stirred at room temperature for 2 h. Subsequently, once more solution 1 was prepared as described above from 274 mg (1.048 mmol) of triphenylphosphine and 203 mul (1.048 mmol) of diisopropyl azodicarboxylate and, together with 152 mg (1.048 mmol) of <strong>[1065267-14-2](3,5-difluoropyridin-2-yl)methanol</strong>, added to the reaction mixture at 0 C. After 2 h at room temperature, the product was purified by preparative HPLC (acetonitrile:water (+0.05% formic acid) gradient). This gave 64 mg of the title compound as a mixture of isomers (N1/N2-alkylated, ratio 4.5:1) (33% of theory). [0715] LC-MS (Method 2): Rt=1.32 min (N2) and 1.36 min (N1); MS (EIpos): m/z=557 [M+H]+

Reference： [1]Patent: US2014/228366,2014,A1 .Location in patent: Paragraph 0713; 0714; 0715

14
[ 1065267-14-2 ]
3-chloro-4-((3,5-difluoropyridin-2-yl)methoxy)-2'-(2-(2-hydroxypropan-2-yl)pyrimidin-4-yl)-5',6-dimethyl-2H-[1,4'-bipyridin]-2-one [ No CAS ]

Reference： [1]Patent: US2014/364442,2014,A1

15
[ 1065267-14-2 ]
3-chloro-4-((3,5-difluoropyridin-2-yl)methoxy)-2'-(2-(2-hydroxypropan-2-yl)pyrimidin-4-yl)-5',6-dimethyl-2H-[1,4'-bipyridin]-2-one [ No CAS ]
3-chloro-4-((3,5-difluoropyridin-2-yl)methoxy)-2'-(2-(2-hydroxypropan-2-yl)pyrimidin-4-yl)-5',6-dimethyl-2H-[1,4'-bipyridin]-2-one [ No CAS ]

Reference： [1]Patent: US2014/364442,2014,A1

16
[ 1065267-14-2 ]
2'-acetyl-3-chloro-4-(3,5-difluoro-pyridin-2-ylmethoxy)-5',6-dimethyl-[1,4]bipyridinyl-2-one [ No CAS ]

Reference： [1]Patent: US2014/364442,2014,A1

17
3,5-difluoro-pyridine-2-carboxylic acid ethyl ester hydrochloride [ No CAS ]
[ 1065267-14-2 ]

Yield	Reaction Conditions	Operation in experiment
1.8 g	With sodium tetrahydroborate; In ethanol; at 0 - 20℃; for 2.5h;	Step B: Preparation of (3,5-difluoro-pyridin-2-yl)-methanol To a solution of 3,5-difluoro-pyridine-2-carboxylic acid ethyl ester of part A (2.5 g, 12.6 mmol) in ethanol (10 mL), cooled using an ice water bath, was added sodium borohydride (1.43 g, 37.8 mmol) in a portion wise manner. The solution was stirred at 0 C. for thirty minutes and at ambient temperature for 2 h. The reaction was returned to 0 C. and saturated ammonium chloride was added dropwise. The solvent was removed in vacuo and the resulting residue was partitioned between ethyl acetate and water. The organic layer was washed with saturated ammonium chloride, water and brine, and dried over magnesium sulfate. The slurry was filtered and concentrated to provide the alcohol as a yellow oil (1.8 g): MS (ES) m/e 146 (M+H).

Reference： [1]Patent: US2014/364442,2014,A1 .Location in patent: Paragraph 0135; 0138; 0139

18
[ 955885-64-0 ]
[ 1065267-14-2 ]

Yield	Reaction Conditions	Operation in experiment
60%	With lithium borohydride; In tetrahydrofuran; at 20℃; for 48h;	Add together methyl 3,5-difluoropyridine-2-carboxylate (1.0 g, 4.6 mmol), THF (10 mL) and 2 M lithium borohydride in THF (15 mL, 23 mmoL). Stir the mixture at room temperature for 2 days. Concentrate under reduced pressure and purify the residue by silica gel chromatography eluting with DCM to give the title compound (0.448 g,60%).

Reference： [1]Patent: WO2015/69512,2015,A1 .Location in patent: Page/Page column 18; 19

19
[ 1065267-14-2 ]
2-[4-[(3,5-difluoro-2-pyridyl)methyl]piperazin-1-yl]-8-methyl-3,5,6,7-tetrahydropyrido[2,3-d]pyrimidin-4-one [ No CAS ]

Reference： [1]Patent: WO2015/69512,2015,A1

20
[ 1065267-14-2 ]
5-(2-chloro-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl)pyridine-2-carbonitrile [ No CAS ]
5-{2-[(3,5-difluoropyridin-2-yl)methoxy]-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl}pyridine-2-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
27 mg		Example 246 5-{2-[(3,5-Difluoropyridin-2-yl)methoxy]-6,7-dihydr o-5H-cyclopenta[b]pyridin-4-yl}pyridine-2-carbonitr ile To 5-(2-chloro-6,7-dihydro-5H-cyclopenta[b]pyridin-4-y l)pyridine-2-carbonitrile (47 mg), <strong>[1065267-14-2](3,5-difluoropyridin-2-yl)methanol</strong> (32 mg), Pd2(dba)3·CHCl3 (11 mg), cesium carbonate (180 mg) and t-Bu-X-Phos (19 mg) was added toluene (1 mL), and the mixture was degassed, then stirred under Ar atmosphere at 100C for 4 hours. After the reaction mixture was allowed to return to room temperature, diluted with ethyl acetate, filtered through Celite, and the filtrate was evaporated under reduced pressure. The resulting residue was dissolved in CH2Cl2 (2 mL), and added with Et3N (0.1 mL) and TFAA (0.05 mL) under ice water cooling, and the mixture was stirred at the same temperature for 2 hours. The reaction mixture was added with ethyl acetate and saturated aqueous sodium hydrogen carbonate solution, and subjected to extraction. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, filtered off, and the filtrate was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography and by recycling preparative gel permeation chromatography (Japan Analytical Industry, Co. Ltd., LC-9201) to give the title compound (27 mg) as colorless oil. [MS (ESI) m/z 365.3 (M+H)+]

Reference： [1]Patent: EP2891656,2015,A1 .Location in patent: Paragraph 0463

21
[ 1065267-14-2 ]
2,4-dichloro-6,7-dihydro-5H-cyclopenta[b]pyridine-1-oxide [ No CAS ]
4-chloro-2-[(3,5-difluoropyridin-2-yl)methoxy]-6,7-dihydro-5H-cyclopenta[b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63 mg		[Step 2] Production of 4-chloro-2-[(3,5-difluoropyridin-2-yl)methoxy]-6,7-dihydro-5H-cyclopenta[b]pyridine To 2,4-dichloro-6,7-dihydro-5H-cyclopenta[b]pyridine 1-oxide (200 mg) and <strong>[1065267-14-2](3,5-difluoropyridin-2-yl)methanol</strong>(185 mg) was added THF (8 mL) and then added NaH (60% dispersion in oil, 59 mg) under ice water cooling, then the mixture was stirred at room temperature for 3 hours. After that phosphorus trichloride (175 mg) was added to the mixture under ice water cooling, and the mixture was stirred for 30 minutes. The reaction mixture was added with aqueous sodium bicarbonate solution, water and ethyl acetate, and subjected to extraction. The organic layer was dried over anhydrous sodium sulfate, filtered off, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give the title compound (63 mg) as a white powder.

Reference： [1]Patent: EP2891656,2015,A1 .Location in patent: Paragraph 0169

22
[ 298709-29-2 ]
[ 1065267-14-2 ]

Reference： [1]Patent: WO2008/117050,2008,A1

23
[ 1065267-14-2 ]
4-(2-((3,5-difluoropyridin-2-yl)methyl)-2H-tetrazol-5-yl)-N-(2-hydroxyethyl)benzenesulfonamide [ No CAS ]

Reference： [1]Patent: WO2019/34729,2019,A1

24
[ 1065267-14-2 ]
C₆H₁₁F₂NO*ClH [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%Spectr.		General procedure: An oven-dried reaction vessel (4 or 9 ml screw-cap vial) equipped with a stirring bar was allowed to cool to room temperature under vacuum. Activated 4 A molecular sieves (crushed, 50 mg), [Rh-2 ] (and solid substrates, 1.0 equiv.), were added under air. The vial was then depressurized and pressurized with argon gas three times before the addition of dry THF (1 M) (and liquid substrates, distilled over CaH2, 1.0 equiv.). Following the addition of 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.0-4.0 equiv. as indicated), the glass vial was placed in a 150 ml stainless-steel autoclave under an argon atmosphere. The autoclave was pressurized and depressurized with hydrogen gas three times before the indicated pressure was set. The reaction mixture was stirred at 25-40 C for 24 h. After the autoclave was carefully depressurized, trifluoroacetic anhydride (3.0 equiv.) and CH2Cl2 (0.5 ml) were added to the crude mixture and stirring was continued for 10 min at room temperature. Alternatively, di-tert-butyl dicarbonate (3.0 equiv.), triethyl amine (3.0 equiv.) and CH2Cl2 (0.5 ml) were added to the reaction mixture and stirring was continued for 2 h at room temperature. The crude was then filtered over fritted funnel and the remaining solid was washed with ethyl acetate (2x 5 ml). The combined solution was concentrated under reduced pressure and submitted to column chromatography (pentane/ethyl acetate or pentane/dichloromethane) to obtain the final product. The indicated diastereoselectivities were determined by GC analysis or from the 19F NMR spectrum immediately after the reaction. NMR yield was calculated using hexafluorobenzene (20 mul, 0.173 mmol) as internal standard.

Reference： [1]Nature Chemistry,2019,vol. 11,p. 264 - 270

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[ 1065267-14-2 ] Synthesis Path-Downstream 1~24

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Fluorinated Building Blocks

Alcohols

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Pyridines

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