[ CAS No. 802325-29-7 ] {[proInfo.proName]}

Name: 802325-29-7|(5-Fluoropyridin-2-yl)methanol|97%
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Quality Control of [ 802325-29-7 ]

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Product Details of [ 802325-29-7 ]

CAS No. :	802325-29-7	MDL No. :	MFCD09027049
Formula :	C₆H₆FNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BKLMFAZXPZQITJ-UHFFFAOYSA-N
M.W :	127.12	Pubchem ID :	24729312
Synonyms :

Safety of [ 802325-29-7 ]

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 [ 802325-29-7 ]

* 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 [ 802325-29-7 ]
Downstream synthetic route of [ 802325-29-7 ]

[ 802325-29-7 ] Synthesis Path-Upstream 1~4

1
[ 41404-58-4 ]
[ 68-12-2 ]
[ 802325-29-7 ]

Yield	Reaction Conditions	Operation in experiment
45%	Stage #1: With n-butyllithium In hexanes; toluene at -78℃; for 1.5 h; Stage #2: at -78℃; for 2 h;	Preparation 56; (5-Fluoro-pyridin-2-yl)-methanol EPO <DP n="164"/>Add butyllithium (10.9 mL, 27.22 mmol, 2.5 M solution in hexanes) to a- 78 ⁰C solution of 2-bromo-5-fluoro-pyridine (3.99 g, 22.68 mmol) in toluene (200 mL). Stir the reaction at -78 ⁰C for 90 min and then add iV.iV-dimethylforrnamide (2.3 mL, 29.71 mmol) via syringe. Stir the reaction for an additional 2 h at -78 ⁰C and then add sodium borohydride (1.72 g, 45.36 mmol) and allow the reaction to warm to room temperature over a 12 h period. Quench the reaction with saturated aqueous sodium bicarbonate (20 mL) and dilute with ethyl acetate (100 mL). Separate the organic phase and dry (magnesium sulfate), filter and concentrate in vacuo to give a yellow oil. Purify the oil by column chromatography (silica gel; 10percent to 50percent ethyl acetate in hexanes) to give 1.30 g (45percent) as a clear colorless oil. ¹H NMR (300 MHz, CDCl₃): δ 8.41s, IH), 7.46-7.37 (m, IH), 7.32-7.27 (m, IH), 4.75 (s, 2H), 3.64 (br s, IH)
36%	Stage #1: With n-butyllithium In hexane; toluene at -78℃; for 0.5 h; Stage #2: at -78 - 0℃; for 0.333333 h;	Manufacturing Example 41-1-1 (5-Fluoro-pyridin-2-yl)-methanol; To a solution of 2-bromo-5-fluoropyridine (3.67 g, 20.8 mmol) in toluene (100 mL) was added dropwise n-butyl lithium (15.6 mL, 1.6 M hexane solution, 25.0 mmol) under nitrogen atmosphere at -78° C., which was stirred for 30 minutes. N,N-Dimethylformamide (8.05 mL, 104.0 mmol) was added dropwise to this solution at -78° C., and stirred for 20 minutes at 0° C. This reaction solution was vigorously stirred after addition of water and tetrahydrofuran. The organic layer was separated, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and filtered. Sodium borohydride (1.58 g, 41.8 mmol) was added to the filtrate at 0° C., and stirred for 1 hour at room temperature. This reaction solution was partitioned by addition of water and tetrahydrofuran. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under a reduced pressure. The resulting residue was purified by NH silica gel column chromatography (hexane:diethyl ether=1:2) to obtain the title compound (945 mg, 36percent).¹H-NMR Spectrum (CDCl₃) δ (ppm): 4.75 (2H, s), 7.29 (1H, dd, J=4.4, 8.8 Hz), 7.43 (1H, ddd, J=2.8, 8.4, 8.4 Hz), 8.42 (1H, d, J=2.8 Hz).

Reference： [1] Patent: WO2007/2181, 2007, A2, . Location in patent: Page/Page column 162-163
[2] Patent: US2009/82403, 2009, A1, . Location in patent: Page/Page column 89
[3] Patent: US2007/72831, 2007, A1, . Location in patent: Page/Page column 97-98

2
[ 148541-70-2 ]
[ 802325-29-7 ]

Yield	Reaction Conditions	Operation in experiment
54%	With lithium borohydride In tetrahydrofuran at 0 - 20℃; for 1 h;	To a solution of ethyl 5-fluoropicolinate (377 mg, 2.23 mmol). in tetrahydrofuran (6 ml), L1BH₄ (73 mg, 3.34 mmol) was added at 0 "C and stirred at room temperature for 1 hour. The reaction was quenched with ice-water and extracted with ethyl acetate, dried (Na₂SO₄) and evaporated under reduced pressure. The residue was purified by column chromatography on silica (ethyl acetate/hexane, 20/80-60/40) to give (5- fluoropyridin-2-yl)methanol (309 mg, 54 percent, colorless oil).

Reference： [1] Patent: WO2008/8398, 2008, A2, . Location in patent: Page/Page column 354
[2] Patent: EP1748048, 2007, A1, . Location in patent: Page/Page column 35

3
[ 107504-08-5 ]
[ 802325-29-7 ]

Yield	Reaction Conditions	Operation in experiment
52%	With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 12 h; Inert atmosphere	A mixture of 14 (500 mg, 4 mmol) and LiAIH₄(202 mg, 5 mmol) in THF (10 mL) was degassed and purged with N₂for 3 times, and then the mixture was stirred at 0 °C for 12 h under N₂atmosphere. The reaction mixture was quenched by saturated sodium potassium tartrate (0.8 mL) at 15 °C, and then filtered. The mixture was diluted with H₂0 (5 mL) and extracted with EtOAc (5 mL x 3). The combined organic layer was washed with brine (5 mL x 2), dried over Na₂S0₄, filtered and concentrated under reduced pressure to give 15 (236 mg, 52percent) as a yellow solid.¹H NMR (400 MHz, DMSO-d₆) 8.43 (d, J - 2.8 Hz, 1 H), 7.45-7.41 (m, 1 H), 7.31-7.27 (m, 1 H), 4.76 (s, 2H). A mixture of 15 (1 g, 8 mmol), DCC (3 g, 16 mmol), DMAP (96 mg, 786 umol) and A/-BOC-(S)-valine (2 g, 9 mmol) in DCM (5 mL) was degassed and purged with N₂for 3 times, and then the mixture was stirred at 25 "C for 12 h under N₂atmosphere. The reaction mixture was filtered and concentrated under reduced pressure. The residue was purified by column chromatography (Si0₂, PE/EtOAc = 5:1) to give 16 (1 .3 g, 51 percent) as a yellow liquid.¹H N R (400 MHz, DMSO-de) 8.55 (s, 1 H), 7.71-7.83 (m, 1 H), 7.54-7.51 (m, 1 H), 7.25 (d, J = 8.0 Hz, 1 H), 5.22-5.13 (m, 2H), 3.91 (t, J = 7.2 Hz, 1 H), 2.06-2.02 (m, 1 H), 1.38 (s, 9H), 0.87 (d, J - 6.4 Hz, 6H).

Reference： [1] Patent: WO2017/195069, 2017, A1, . Location in patent: Page/Page column 61

4
[ 31181-88-1 ]
[ 802325-29-7 ]

Reference： [1] Patent: US2007/105904, 2007, A1, . Location in patent: Page/Page column 87

[ 802325-29-7 ] Synthesis Path-Downstream 1~47

1
[ 802325-29-7 ]
[ 915409-01-7 ]

Yield	Reaction Conditions	Operation in experiment
33%		Preparation 57; 2-Chloromethyl-5-fluoro-pyridine hydrochloride salt HCIAdd thionyl chloride (320 muL, 4.30 mmol) slowly to a 0 0C solution of (5- fluoro-pyridm-2-yl)-methanol (420 mg, 3.31 mmol) in methylene chloride (15 mL). Stir the reaction at 0 0C for 3 h and quench with isopropyl alcohol. Dilute the reaction contents with methylene chloride (50 mL) and then saturated aqueous sodium bicarbonate (20 mL). Separate the organic phase, dry(magnesium sulfate), filter and concentrate in vacuo to give an oil. The oil is treated with hydrochloric acid (10 mL, 3 M solution in dioxane) at room temperature for 30 min. The resultant solid is collected by filtration and washed with a minimal amount of cold diethyl ether to give 200 mg (33%) as a yellow solid. MS (APCI): m/z 146[C6H5ClFN + H]+; 1H NMR (300 MHz, CDCl3): delta 8.42 (s, IH), 7.56-7.37 (m, 2H), 4.67 (s, 2H).
102 mg	With thionyl chloride; In dichloromethane; at 20℃;Inert atmosphere;	To a mixture of <strong>[802325-29-7]5-fluoro-2-hydroxymethylpyridine</strong> (purchased from Ark Pharm Inc.), (250 mg) in anhydrous DCM (8.4 mL) stirred at rt under nitrogen, was added thionyl chloride (0.29 mL). The reaction was stirred at rt overnight, at which point LC-MS indicated presence of the product. The reaction was then concentrated in vacuo and re-dissolved in DCM (10 mL) and concentrated in vacuo again to give 2-(chloromethyl)-5-fluoropyridine hydrochloride (102 mg), which was added to a mixture of 7-chloro-N-((1S,2S)-2-hydroxycyclohexyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide (Intermediate 17), (150 mg), and cesium carbonate (383 mg) in DMF (3 mL) and left to stir at rt over the weekend. The crude product was purified by prep. LC-MS to give the desired compound (129 mg).
102 mg	With thionyl chloride; In dichloromethane; at 20℃;Inert atmosphere;	To a mixture of <strong>[802325-29-7]5-fluoro-2-hydroxymethylpyridine</strong> (purchased from Ark Pharm Inc.), (250 mg) in anhydrous DCM (8.4 mL) stirred at rt under nitrogen, was added thionyl chloride (0.29 mL). The reaction was stirred at rt overnight, at which point LC-MS indicated presence of the product. The reaction was then concentrated in vacuo and re-dissolved in DCM (10 mL) and concentrated in vacuo again to give 2-(chloromethyl)-5-fluoropyridine hydrochloride (102 mg), which was added to a mixture of 7-chloro-N-((1S,2S)-2-hydroxycyclohexyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxamide (Intermediate 17), (150 mg), and cesium carbonate (383 mg) in DMF (3 mL) and left to stir at rt over the weekend. The crude product was purified by prep. LC-MS to give the desired compound (129 mg).

With thionyl chloride; In dichloromethane; at 20℃; for 16h;Inert atmosphere;

Thionyl chloride (0.419 mL, 5.74 mmol, commercial source: Aldrich) was added dropwise to a stirred solution of [802325-29-7](5-fluoropyridin-2-yl)methanol (0.289 mL, 2.87 mmol, commercial source: Combi-Blocks) in Dichloromethane (5.74 mL) under nitrogen at rt. The mixture was stirred at rt for 16 h. The mixture was concentrated under reduced pressure to yield 2-(chloromethyl)-5- fluoropyridine hydrochloride (395 mg, 2.170 mmol, 76%) that was used in the next step without further purification.1H NMR (400 MHz, DMSO-d6) delta 1 1 .68 (br s, 1 H), 8.55 (d, J = 3.0 Hz, 1 H), 7.77 (dt, J = 8.7, 3.0 Hz, 1 H), 7.63 (dd, J = 8.6, 4.5 Hz, 1 H), 4.78 (s, 2H). MS m/z [M+H]+= 146.10.

Reference： [1]Patent: WO2007/2181,2007,A2 .Location in patent: Page/Page column 163
[2]Patent: US2015/94328,2015,A1 .Location in patent: Paragraph 0626
[3]Patent: WO2015/49574,2015,A1 .Location in patent: Page/Page column 77
[4]Patent: WO2019/34729,2019,A1 .Location in patent: Page/Page column 37

2
[ 148541-70-2 ]
[ 802325-29-7 ]

Yield	Reaction Conditions	Operation in experiment
54%	With lithium borohydride; In tetrahydrofuran; at 0 - 20℃; for 1h;	To a solution of ethyl 5-fluoropicolinate (377 mg, 2.23 mmol). in tetrahydrofuran (6 ml), L1BH4 (73 mg, 3.34 mmol) was added at 0 "C and stirred at room temperature for 1 hour. The reaction was quenched with ice-water and extracted with ethyl acetate, dried (Na2SO4) and evaporated under reduced pressure. The residue was purified by column chromatography on silica (ethyl acetate/hexane, 20/80-60/40) to give (5- fluoropyridin-2-yl)methanol (309 mg, 54 %, colorless oil).
		Production Example 5-3: (5-Fluoropyridin-2-yl)methanol: A THF solution (50 mL) of the compound (1.1 g) obtained in Production Example 5-2 was cooled to 0C, and in a nitrogen atmosphere, a toluene solution (19.5 mL) of 1 M diisobutylaluminium hydride was dropwise added thereto at an inner temperature not higher than 5C. This was stirred at 0C for 30 minutes, and then sodium borohydride (246 mg) and methanol (2 mL) were added to the reaction solution and stirred at room temperature for 30 minutes. Sodium sulfate 10-hydrate was added to the reaction solution, and stirred overnight at room temperature. The reaction solution was filtered through Celite, and the solvent was evaporated off from the filtrate under reduced pressure. The resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate = 9/1 to 3/2) to obtain the entitled compound (800 mg).;

Reference： [1]Patent: WO2008/8398,2008,A2 .Location in patent: Page/Page column 354
[2]Patent: EP1748048,2007,A1 .Location in patent: Page/Page column 35

3
[ 41404-58-4 ]
[ 68-12-2 ]
[ 802325-29-7 ]

Yield	Reaction Conditions	Operation in experiment
45%		Preparation 56; (5-Fluoro-pyridin-2-yl)-methanol EPO <DP n="164"/>Add butyllithium (10.9 mL, 27.22 mmol, 2.5 M solution in hexanes) to a- 78 0C solution of 2-bromo-5-fluoro-pyridine (3.99 g, 22.68 mmol) in toluene (200 mL). Stir the reaction at -78 0C for 90 min and then add iV.iV-dimethylforrnamide (2.3 mL, 29.71 mmol) via syringe. Stir the reaction for an additional 2 h at -78 0C and then add sodium borohydride (1.72 g, 45.36 mmol) and allow the reaction to warm to room temperature over a 12 h period. Quench the reaction with saturated aqueous sodium bicarbonate (20 mL) and dilute with ethyl acetate (100 mL). Separate the organic phase and dry (magnesium sulfate), filter and concentrate in vacuo to give a yellow oil. Purify the oil by column chromatography (silica gel; 10% to 50% ethyl acetate in hexanes) to give 1.30 g (45%) as a clear colorless oil. 1H NMR (300 MHz, CDCl3): delta 8.41s, IH), 7.46-7.37 (m, IH), 7.32-7.27 (m, IH), 4.75 (s, 2H), 3.64 (br s, IH)
36%		Manufacturing Example 41-1-1 (5-Fluoro-pyridin-2-yl)-methanol; To a solution of 2-bromo-5-fluoropyridine (3.67 g, 20.8 mmol) in toluene (100 mL) was added dropwise n-butyl lithium (15.6 mL, 1.6 M hexane solution, 25.0 mmol) under nitrogen atmosphere at -78 C., which was stirred for 30 minutes. N,N-Dimethylformamide (8.05 mL, 104.0 mmol) was added dropwise to this solution at -78 C., and stirred for 20 minutes at 0 C. This reaction solution was vigorously stirred after addition of water and tetrahydrofuran. The organic layer was separated, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and filtered. Sodium borohydride (1.58 g, 41.8 mmol) was added to the filtrate at 0 C., and stirred for 1 hour at room temperature. This reaction solution was partitioned by addition of water and tetrahydrofuran. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under a reduced pressure. The resulting residue was purified by NH silica gel column chromatography (hexane:diethyl ether=1:2) to obtain the title compound (945 mg, 36%).1H-NMR Spectrum (CDCl3) delta (ppm): 4.75 (2H, s), 7.29 (1H, dd, J=4.4, 8.8 Hz), 7.43 (1H, ddd, J=2.8, 8.4, 8.4 Hz), 8.42 (1H, d, J=2.8 Hz).
		(Related precendent, see Reider et al., Tett. Lett., 41, 2000, 4335-4338). Into a flask containing 2-Bromo-5-fluoro-pyridine (purchased from Aldrich, 2.5 g, 14.30 mmol, 1 eq) was dissolved toluene (143 mL, 0.1 M) and DMF (1.44 mL, 18.58 mmol, 1.3 eq, anhydrous) before being cooled to 78 C. under an inert atmosphere. nBuLi (17.1 mL, 17.14 mmol, 1 M hexanes) was added dropwise via an addition funnel over 15 min and allowed to stir for 90 min. To the mixture was added NaBH4 (1.08 g, 28.60 mmol, 2 eq) and the reaction allowed to warm up to room temp. The reaction was quenched with saturated NH4Cl and dissolved in EtOAc (300 mL). It was washed with water (2×100 mL) and brine (100 mL). The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. Flash column chromatography was used to purify the product using hexanes/Ethyl acetate (3/7) as eluent to furnish desired alcohol 148. 1H NMR (300 MHz) CDCl3 delta: partial 4.75 (s, 2H), 3.67 (bs, 1H). 19F NMR (300 MHz) CDCl3 delta: -129.80. MS: 127.96 (M+1).

Reference： [1]Patent: WO2007/2181,2007,A2 .Location in patent: Page/Page column 162-163
[2]Patent: US2009/82403,2009,A1 .Location in patent: Page/Page column 89
[3]Patent: US2007/72831,2007,A1 .Location in patent: Page/Page column 97-98

4
[ 31181-88-1 ]
[ 802325-29-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tetrahydroborate; In tetrahydrofuran; hexane; toluene; at 0 - 20℃; for 1h;	To a solution of 2-bromo-5-fluoropyridine (3.67 g, 20.8 mmol) in toluene (100 mL) was added dropwise n-butyl lithium (15.6 mL, 1.6 M hexane solution, 25.0 mmol) under nitrogen atmosphere at -78 C., which was stirred for 30 minutes. N,N-Dimethylformamide (8.05 mL, 104.0 mmol) was added dropwise to this solution at -78 C., and stirred for 20 minutes at 0 C. This reaction solution was vigorously stirred after addition of water and tetrahydrofuran. The organic layer was separated, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and filtered. Sodium borohydride (1.58 g, 41.8 mmol) was added to the filtrate at 0 C., and stirred for 1 hour at room temperature. This reaction solution was partitioned by addition of water and tetrahydrofuran. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under a reduced pressure. The resulting residue was purified by NH silica gel column chromatography (hexane:diethyl ether=1:2) to obtain the title compound (945 mg, 36%). 1H-NMR Spectrum (CDCl3) delta (ppm): 4.75 (2H, s), 7.29 (1H, dd, J=4.4, 8.8 Hz), 7.43 (1H, ddd, J=2.8, 8.4, 8.4 Hz), 8.42 (1H, d, J=2.8 Hz).

Reference： [1]Patent: US2007/105904,2007,A1 .Location in patent: Page/Page column 87

5
[ 802325-29-7 ]
2-(chloromethyl)-5-fluoropyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%		Manufacturing Example 41-1-2 2-Chloromethyl-5-fluoro-pyridine; To a solution of <strong>[802325-29-7](5-fluoro-pyridin-2-yl)-methanol</strong> (945 mg, 7.43 mmol) described in Manufacturing Example 41-1-1 in methylene chloride (70 mL) was added dropwise thionyl chloride (813 muL, 11.1 mmol) at room temperature, which was stirred for 30 minutes. This reaction solution was partitioned by addition of water, sodium hydrogencarbonate and methylene chloride. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under a reduced pressure. The residue was purified by NH silica gel column chromatography (hexane:diethyl ether=1:1) to obtain the title compound (761.1 mg, 70%).1H-NMR Spectrum (CDCl3) delta (ppm): 4.67 (2H, s), 7.26-7.51 (2H, m), 8.43 (1H, d, J=2.8 Hz).
70%		To a solution of <strong>[802325-29-7](5-fluoro-pyridin-2-yl)-methanol</strong> (945 mg, 7.43 mmol) described in Manufacturing Example 41-1-1 in methylene chloride (70 mL) was added dropwise thionyl chloride (813 muL, 11.1 mmol) at room temperature, which was stirred for 30 minutes. This reaction solution was partitioned by addition of water, sodium hydrogencarbonate and methylene chloride. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under a reduced pressure. The residue was purified by NH silica gel column chromatography (hexane:diethyl ether=1:1) to obtain the title compound (761.1 mg, 70%). 1H-NMR Spectrum (CDCl3) delta (ppm): 4.67 (2H, s), 7.26-7.51 (2H, m), 8.43 (1H, d, J=2.8 Hz).
620 mg	With thionyl chloride; In dichloromethane; at 20℃; for 1h;	To a stirred solution of <strong>[802325-29-7](5-fluoropyridin-2-yl) methanol</strong> 5 (500 mg, 3.94 mmol) in CH2C12 (40 mL) at RT under an inert atmosphere, was added SOd2 (0.43 mL, 5.9 mmol) drop wise and the mixture stirred for 1 h. The reaction mixture was quenched with saturated NaHCO3 (40 mL) and extracted with CH2C12 (2 x 50 mL). The combined organic extracts were washed with water (20 mL), brine (20 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to afford compound 3 (620 mg) as pale brown viscous liquid. This material was used without purification.

With thionyl chloride; In dichloromethane; at 28℃; for 2h;

To a solution of [802325-29-7](5-fluoropyridin-2-yl)methanol (10 g, 0.0787 mol, commercial source: Combi- Blocks) in dichloromethane (200 mL), thionyl chloride (18.72 g, 0.1574 mol, commercial source: Avra) was slowly added at 0 C. The reaction mixture was allowed to 28 C and stirred for 2 h. On completion, the reaction mixture was cooled to 0 C, quenched with saturated ammonium chloride solution (200 mL) and extracted with dichloromethane (5x100 mL). The organic layer was dried over Na2S04, filtered and the filtrate was concentrated under reduced pressure to afford 2-(chloromethyl)-5-fluoropyridine (7 g, 47%) as a yellow liquid that was characterized by H-NMR. This crude was used without any purification in the next reaction.1H NMR (400 MHz, CDCI3) delta 8.43 (d, J = 2.8 Hz, 1 H), 7.53-7.40 (m, 2H), 4.67 (s, 2H).

Reference： [1]Patent: US2009/82403,2009,A1 .Location in patent: Page/Page column 89
[2]Patent: US2007/105904,2007,A1 .Location in patent: Page/Page column 87
[3]Patent: WO2016/144702,2016,A1 .Location in patent: Paragraph 00369
[4]Patent: WO2019/34729,2019,A1 .Location in patent: Page/Page column 36; 37

6
[ 802325-29-7 ]
[ 1160938-20-4 ]
[ 1160938-49-7 ]

Yield	Reaction Conditions	Operation in experiment
44%	With di-tert-butyl (E)-azodicarboxylate; triphenylphosphine; In dichloromethane;	A solution of 6'-[3-(dimethylamino)-1-pyrrolidinyl]-4-hydroxy-2/-/-1 ,3'-bipyridin-2-one (100 mg, 0.333 mmol) and triphenylphosphine (140 mg, 0.533 mmol) in dichloromethane (5 ml) was treated with <strong>[802325-29-7](5-fluoro-2-pyridinyl)methanol</strong> (50.8 mg, 0.400 mmol) followed by bis(1 ,1-dimethylethyl) (E)-1 ,2-diazenedicarboxylate (123 mg, 0.533 mmol). After stirring overnight, the reaction was treated with additional (5- fluoro-2-pyridinyl)methanol (50.8 mg, 0.400 mmol), triphenylphosphine (140 mg, 0.533 mmol), and bis(1 ,1-dimethylethyl) (E)- 1 ,2-diazenedicarboxylate (123 mg, 0.533 mmol). After stirring for 2 h, the reaction was concentrated in vacuo and residue purified via Agilent semi-prep HPLC using 5-50% CH3CN/H2O. The resulting residue was treated with saturated aqueous NaHCC>3 solution and extracted with EtOAc. The combined extracts were dried (IS^SC^), filtered, and concentrated in vacuo to give the title compound (61 mg, 44%): 1H NMR (400 MHz, CDCI3) delta ppm 8.46 (s, 1 H), 8.05 (d, J = 2.7 Hz, 1 H), 7.51-7.41 (m, 3 H), 7.19 (d, J = 7.6 Hz, 1 H), 6.39 (d, J = 9.0 Hz, 1 H), 6.06 (dd, J = 7.6, 2.7 Hz, 1 H), 6.01 (d, J = 2.4 Hz, 1 H), 5.13 (s, 2 H), 3.79 (t, J = 8.3 Hz, 1 H), 3.65 (t, J = 9.4 Hz, 1 H), 3.47-3.36 (m, 1 H), 3.33-3.20 (m, 1 H), 2.81 (br s, 1 H), 2.32 (s, 6 H), 2.29-2.18 (m, 1 H), 2.01-1.86 (m, 1 H); ES-LCMS m/z 410 {M+H)+.

Reference： [1]Patent: WO2009/76387,2009,A1 .Location in patent: Page/Page column 59

7
[ 1121-76-2 ]
[ 802325-29-7 ]
[ 1173155-63-9 ]

Yield	Reaction Conditions	Operation in experiment
50%		5-Fluoro-2-pyridylbenzylalcohol (3.00 g, 23.6 mmol) was dissolved in DMF (20 mL), and NaH (60% weight dispersion in mineral oil, 0.92 g, 23 mmol) was added. After ?tauiotarhorhoiotanugamma for 30 minutes, 4-chloropyridine-N-oxide (2.03 g, 15.7 mmol) was added, and the reaction mixture was heated for 1 h at 120 C. Upon cooling, the mixture was diluted with methylene chloride and washed with 5% lithium chloride solution (5×), dried and concentrated. Purification by flash column chromatography (40 g ISCO column eluting with methylene chloride and a methanol/ammonia mixture (10:1); gradient 100% methylene chloride to 90% methylene chloride over 30 min at 40 mL/min) provided the title compound (1.76 g, 50%) as a tan solid: 1H NMR (300 MHz, CDCl3) delta 8.48 (s, 1H), 8.12 (d, J=7.7 Hz, 2H), 7.48-7.46 (m, 2H), 6.90 (d, J=7.7 Hz, 2H), 5.20 (s, 2H).
50%		5-Fluoro-2-pyridylbenzylalcohol (3.00 g, 23.6 mmol) was dissolved in DMF (20 mL), and NaH (60% weight dispersion in mineral oil, 0.92 g, 23 mmol) was added. After stirring for 30 minutes, 4-chloropyridine-N-oxide (2.03 g, 15.7 mmol) was added, and the reaction mixture was heated for 1 h at 120 C. Upon cooling, the mixture was diluted with methylene chloride and washed with 5% lithium chloride solution (5×), dried and concentrated. Purification by flash column chromatography (40 g ISCO column eluting with methylene chloride and a methanol/ammonia mixture (10:1); gradient 100% methylene chloride to 90% methylene chloride over 30 min at 40 mL/min) provided the title compound (1.76 g, 50%) as a tan solid: 1H NMR (300 MHz, CDCl3) delta 8.48 (s, 1H), 8.12 (d, J=7.7 Hz, 2H), 7.48-7.46 (m, 2H), 6.90 (d, J=7.7 Hz, 2H), 5.20 (s, 2H).
50%		5-Fluoro-2-pyridylbenzylalcohol (3.00 g, 23.6 mmol) was dissolved in DMF (20 mL), and NaH (60% weight dispersion in mineral oil, 0.92 g, 23 mmol) was added. After stirring for 30 minutes, 4-chloropyridine-N-oxide (2.03 g, 15.7 mmol) was added, and the reaction mixture was heated for 1 h at 120 C. Upon cooling, the mixture was diluted with methylene chloride, washed with 5% lithium chloride solution (5*), dried, and concentrated. Purification by flash column chromatography (40 g ISCO column eluting with methylene chloride and a methanol/ammonia mixture (10:1); gradient 100% methylene chloride to 90% methylene chloride over 30 min at 40 mL/min) provided the title compound (1.76 g, 50%) as a tan solid: 1H NMR (300 MHz, CDCl3) delta 8.48 (s, 1H), 8.12 (d, J=7.7 Hz, 2H), 7.48-7.46 (m, 2H), 6.90 (d, J=7.7 Hz, 2H), 5.20 (s, 2H).

With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 120℃; for 1h;

5-Fluoro-2-pyridylbenzylalcohol (3.00 g, 23.6 mmol) was dissolved in DMF (20 mL), and NaH (60% weight dispersion in mineral oil, 0.92 g, 23 mmol) was added. After stirring for 30 minutes, 4-chloropyridine-N-oxide (2.03 g, 15.7 mmol) was added, and the reaction mixture was heated for 1 h at 120 C. Upon cooling, the mixture was diluted with methylene chloride and washed with 5% lithium chloride solution (5×), dried and concentrated. Purification by flash column chromatography (40 g ISCO column eluting with methylene chloride and a methanol/ammonia mixture (10:1); gradient 100% methylene chloride to 90% methylene chloride over 30 min at 40 mL/min) provided the title compound (1.76 g, 50%) as a tan solid: 1H NMR (300 MHz, CDCl3) delta 8.48 (s, 1H), 8.12 (d, J=7.7 Hz, 2H), 7.48-7.46 (m, 2H), 6.90 (d, J=7.7 Hz, 2H), 5.20 (s, 2H).

Reference： [1]Patent: US2011/3738,2011,A1 .Location in patent: Page/Page column 26
[2]Patent: US2011/3739,2011,A1 .Location in patent: Page/Page column 20
[3]Patent: US2012/157460,2012,A1 .Location in patent: Page/Page column 25
[4]Patent: US2011/3793,2011,A1 .Location in patent: Page/Page column 41-42

8
[ 802325-29-7 ]
[ 924311-90-0 ]

Reference： [1]Patent: US2012/157460,2012,A1

9
[ 802325-29-7 ]
[ 1382804-98-9 ]

Reference： [1]Patent: US2012/157460,2012,A1

10
[ 802325-29-7 ]
[ 1382804-97-8 ]

Reference： [1]Patent: US2012/157460,2012,A1

11
[ 802325-29-7 ]
5-tert-butyl-3-(4-chloro-5-cyclopropylpyridin-2-yl)-1,2,4-oxadiazole [ No CAS ]
5-tert-butyl-3-[5-cyclopropyl-4-[(5-fluoropyridin-2-yl)methoxy]pyridin-2-yl]-1,2,4-oxadiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		The title compound was synthesized in analogy to Example 48e, using 5-tert-butyl-3-(4- chloro-5-cyclopropylpyridin-2-yl)- 1 ,2,4-oxadiazole and <strong>[802325-29-7]5-fluoro-2-hydroxylmethylpyridine</strong> (CAS 802325-29-7) as starting materials, heated 30 min at 110C under microwave radiation. The mixture was diluted with ethyl acetate and extracted with aqueous Na2C03. Organic phase was collected and the aqueous phase was back-extracted with ethyl acetate. The organic phases were combined, dried over Na2S04 and evaporated down to dryness. The crude material was purified by flash chromatography (Si02, 5 g, ethyl acetate/heptane). MS (ESI, m/z): 369.6 (MH+).

Reference： [1]Patent: WO2014/154612,2014,A1 .Location in patent: Page/Page column 114; 115

12
[ 802325-29-7 ]
5-(2-chloro-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl)pyridine-2-carbonitrile [ No CAS ]
5-{2-[(5-fluoropyridin-2-yl)methoxy]-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl}pyridine-2-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
11 mg		[Step 6] Production of 5-{2-[(5-fluoropyridin-2-yl)methoxy]-6,7-dihydro-5H -cyclopenta[b]pyridin-4-yl}pyridine-2-carbonitrile To 5-(2-chloro-6,7-dihydro-5H-cyclopenta[b]pyridin-4-y l)pyridine-2-carbonitrile (60 mg), <strong>[802325-29-7](5-fluoropyridin-2-yl)methanol</strong> (36 mg), t-Bu-X-Phos (24 mg), NaO-t-Bu (45 mg), Pd2(dba)3·CHCl3 (10 mg) and molecular sieve 4A (hereinafter referred to as 'MS4A') was added toluene (1 mL), and the mixture was degassed, then stirred under Ar atmosphere at 100C for 1 hour. After the reaction mixture was allowed to return to room temperature, diluted with diethyl acetate filtered through Celite, and the filtrate was evaporated under reduced pressure. The resulting residue was dissolved in CH2Cl2 (3 mL), and then Et3N (0.1 mL) and TFAA (0.05 mL) were added to the mixture under ice water cooling under Ar atmosphere, and the mixture was stirred at the same temperature for 2 hours. The resulting mixture was added with water and ethyl acetate, and subjected to extraction. The organic layer was washed with saturated brine, 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 (11 mg). [MS (ESI) m/z 347.3 (M+H)+]

Reference： [1]Patent: EP2891656,2015,A1 .Location in patent: Paragraph 0126

13
[ 802325-29-7 ]
2-chloro-4-[(4-methoxybenzyl)oxy]-5,6,7,8-tetrahydroquinoline [ No CAS ]
2-[(5-fluoropyridin-2-yl)methoxy]-4-[(4-methoxybenzyl)oxy]-5,6,7,8-tetrahydroquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
287 mg	With 4,5-bis-(di-tert-butyl-phosphanyl)-9,9-dimethyl-9H-xanthene; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; In toluene; at 100℃; for 2h;Inert atmosphere;	[Step 1] Production of 2-[(5-fluoropyridin-2-yl)methoxy]-4-[(4-methoxybenz yl)oxy]-5,6,7,8-tetrahydroquinoline To 2-chloro-4-[(4-methoxybenzyl)oxy]-5,6,7,8-tetrahydr oquinoline (450 mg), <strong>[802325-29-7](5-fluoropyridin-2-yl)methanol</strong> (226 mL), Pd2(dba)3 (136 mg), t-Bu-X-Phos (151 mg) and NaO-t-Bu (285 mg) was added toluene (10 mL), and the mixture was degassed, then stirred under Ar atmosphere at 100C for 2 hours. After the reaction mixture was allowed to return to room temperature, the reaction mixture was added with water and ethyl acetate, and subjected to extraction. The organic layer was 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 to give the title compound (287 mg) as a yellow solid.

Reference： [1]Patent: EP2891656,2015,A1 .Location in patent: Paragraph 0384

14
[ 802325-29-7 ]
4-[6-([tert-butyl(dimethyl)silyl]oxy}methyl)pyrazin-2-yl]-2-chloro-5,6,7,8-tetrahydroquinoline [ No CAS ]
4-[6-([tert-butyl(dimethyl)silyl]oxy}methyl)pyrazin-2-yl]-2-[(5-fluoropyridin-2-yl)methoxy]-5,6,7,8-tetrahydroquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59 mg	With 4,5-bis-(di-tert-butyl-phosphanyl)-9,9-dimethyl-9H-xanthene; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; In toluene; at 100℃;Inert atmosphere;	[Step 1] Production of 4-[6-([tert-butyl(dimethyl)silyl]oxy}methyl)pyrazi n-2-yl]-2-[(5-fluoropyridin-2-yl)methoxy]-5,6,7,8-t etrahydroquinoline To 4-[6-([tert-butyl(dimethyl)silyl]oxy}methyl)pyrazi n-2-yl]-2-chloro-5,6,7,8-tetrahydroquinoline (80 mg), <strong>[802325-29-7](5-fluoropyridin-2-yl)methanol</strong> (31 mg), Pd2(dba)3 (11 mg), t-Bu-X-Phos (21 mg) and NaO-t-Bu (39 mg) was added toluene (2 mL), and the mixture was degassed, and then stirred under Ar atmosphere at 100C overnight. 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 purified by silica gel column chromatography to give the title compound (59 mg) as yellow oil.

Reference： [1]Patent: EP2891656,2015,A1 .Location in patent: Paragraph 0422

15
[ 802325-29-7 ]
[ 124-63-0 ]
(5-fluoropyridin-2-yl)methyl methanesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃;	Methanesulfonyl chloride (0.91 mL, 12 mmol) was added to a mixture of <strong>[802325-29-7](5-fluoropyridin-2-yl)methanol</strong> (Pharmablock, catNo.PB112906) (1.00 g, 7.87 mmol), and N,N-diisopropylethylamine (2.0 mL, 12 mmol) in methylene chloride (20 mL) at 0 C. The reaction mixture was stirred at room temperature overnight, and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column (gradient elution with ethyl acetate in hexanes (0-55%)) to afford the desired product (0.63 g, 39%). LC-MS calculated for C7H9FNO3S [M+H]+: m/z=206.0. found 206.1.
	With N-ethyl-N,N-diisopropylamine; In dichloromethane;	Step 1: (5-fluoropyridin-2-yl)methyl methanesulfonate Methanesulfonyl chloride (0.91 mL, 12 mmol) was added to a mixture of <strong>[802325-29-7](5-fluoropyridin-2-yl)methanol</strong> (Pharmablock, cat#PB112906: 1.00 g, 7.87 mmol), and N,N-diisopropylethylamine (2.0 mL, 12 mmol) in methylene chloride (20 mL) at 0 C. The reaction mixture was stirred at room temperature overnight, and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column (gradient elution with ethyl acetate in hexanes (0-55%)) to afford the desired product (0.63 g, 39%). LC-MS calculated for C7H9FNO3S [M+H]+: m/z=206.0. found 206.1.
	With triethylamine; In dichloromethane; at 0℃; for 0.166667h;	To a sol. of <strong>[802325-29-7](5-fluoropyridin-2-yl)methanol</strong> (339 mg, 2.64 mmol) and EfeN (0.551 mL, 3.96 mmol) in CH2CI2 (13 mL) is added at 0 C methansulfonyl chloride (225muIota, 2.9 mmol). The mixture is stirred at 0 C for 10 min. Aq. sat. NaHC03 is added, and the phases are separated. The aq. layer is extracted with CH2CI2 several times. The combined org. layers are washed with brine, dried over Na2S04, filtered and evaporated under reduced pressure to yield the example 106. LC-MS: tR = 0.45 min, MH+ = 206.22 (conditions 4).

0.3 g

With triethylamine; In dichloromethane; at 20℃; for 2h;Cooling with ice;

To an ice cold solution of [802325-29-7](5-fluoropyridin-2-yl)methanol (0.25 g, 1.96 mmol) in DCM (10 mL) was added triethyl amine (0.8 mL, 5.90 mmol) followed by methane sulphonyl chloride (0.23 mL, 2.95 mmol). The mixture was stirred at RT for 2 h. The mixture was diluted with DCM and washed with water. The organic layer was dried over sodium sulphate and concentrated under reduced pressure to afford the title compound as brown gummy mass (0.3 g). LC-MS: m/z 206.1 (M+H)+ .

Reference： [1]Patent: US2015/225401,2015,A1 .Location in patent: Paragraph 0770; 0771
[2]Patent: US2015/225379,2015,A1
[3]Patent: WO2015/186056,2015,A1 .Location in patent: Page/Page column 72
[4]Patent: WO2016/203112,2016,A1 .Location in patent: Page/Page column 62

16
[ 802325-29-7 ]
5-fluoro-2-((3-nitro-1H-pyrazol-1-yl)methyl)pyridine [ No CAS ]

Reference： [1]Patent: WO2015/186056,2015,A1

17
[ 802325-29-7 ]
1-((5-fluoropyridin-2-yl)methyl)-1H-pyrazol-3-amine [ No CAS ]

Reference： [1]Patent: WO2015/186056,2015,A1

18
[ 802325-29-7 ]
2-((1-((5-fluoropyridin-2-yl)methyl)-1H-indol-4-yl)oxy)isonicotinonitrile [ No CAS ]

Reference： [1]Patent: WO2016/144702,2016,A1

19
[ 802325-29-7 ]
(2-((1-((5-fluoropyridin-2-yl)methyl)-1H-indol-4-yl)oxy) pyridin-4-yl)methanamine hydrochloride [ No CAS ]

Reference： [1]Patent: WO2016/144702,2016,A1

20
[ 802325-29-7 ]
7'-((5-fluoropyridin-2-yl)methoxy)-1'-(4-methoxybenzyl)-5'-nitrospiro[cyclobutane-1,3'-indolin]-2'-one [ No CAS ]

Reference： [1]Patent: WO2016/203112,2016,A1

21
[ 802325-29-7 ]
C₁₁H₁₅FN₂O₂*ClH [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 6 - 10
[2]Patent: WO2017/195069,2017,A1

22
[ 802325-29-7 ]
C₂₀H₂₂BFN₂O₅ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 6 - 10

23
[ 802325-29-7 ]
[ 13734-41-3 ]
C₁₆H₂₃FN₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 25℃; for 12h;Inert atmosphere;	A mixture of 14 (500 mg, 4 mmol) and LiAIH4(202 mg, 5 mmol) in THF (10 mL) was degassed and purged with N2for 3 times, and then the mixture was stirred at 0 C for 12 h under N2atmosphere. The reaction mixture was quenched by saturated sodium potassium tartrate (0.8 mL) at 15 C, and then filtered. The mixture was diluted with H20 (5 mL) and extracted with EtOAc (5 mL x 3). The combined organic layer was washed with brine (5 mL x 2), dried over Na2S04, filtered and concentrated under reduced pressure to give 15 (236 mg, 52%) as a yellow solid.1H NMR (400 MHz, DMSO-d6) 8.43 (d, J - 2.8 Hz, 1 H), 7.45-7.41 (m, 1 H), 7.31-7.27 (m, 1 H), 4.76 (s, 2H). A mixture of 15 (1 g, 8 mmol), DCC (3 g, 16 mmol), DMAP (96 mg, 786 umol) and A/-BOC-(S)-valine (2 g, 9 mmol) in DCM (5 mL) was degassed and purged with N2for 3 times, and then the mixture was stirred at 25 "C for 12 h under N2atmosphere. The reaction mixture was filtered and concentrated under reduced pressure. The residue was purified by column chromatography (Si02, PE/EtOAc = 5:1) to give 16 (1 .3 g, 51 %) as a yellow liquid.1H N R (400 MHz, DMSO-de) 8.55 (s, 1 H), 7.71-7.83 (m, 1 H), 7.54-7.51 (m, 1 H), 7.25 (d, J = 8.0 Hz, 1 H), 5.22-5.13 (m, 2H), 3.91 (t, J = 7.2 Hz, 1 H), 2.06-2.02 (m, 1 H), 1.38 (s, 9H), 0.87 (d, J - 6.4 Hz, 6H).

Reference： [1]Patent: WO2017/195069,2017,A1 .Location in patent: Page/Page column 61; 62
[2]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 6 - 10

24
[ 107504-08-5 ]
[ 802325-29-7 ]

Yield	Reaction Conditions	Operation in experiment
52%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0℃; for 12h;Inert atmosphere;	A mixture of 14 (500 mg, 4 mmol) and LiAIH4(202 mg, 5 mmol) in THF (10 mL) was degassed and purged with N2for 3 times, and then the mixture was stirred at 0 C for 12 h under N2atmosphere. The reaction mixture was quenched by saturated sodium potassium tartrate (0.8 mL) at 15 C, and then filtered. The mixture was diluted with H20 (5 mL) and extracted with EtOAc (5 mL x 3). The combined organic layer was washed with brine (5 mL x 2), dried over Na2S04, filtered and concentrated under reduced pressure to give 15 (236 mg, 52%) as a yellow solid.1H NMR (400 MHz, DMSO-d6) 8.43 (d, J - 2.8 Hz, 1 H), 7.45-7.41 (m, 1 H), 7.31-7.27 (m, 1 H), 4.76 (s, 2H). A mixture of 15 (1 g, 8 mmol), DCC (3 g, 16 mmol), DMAP (96 mg, 786 umol) and A/-BOC-(S)-valine (2 g, 9 mmol) in DCM (5 mL) was degassed and purged with N2for 3 times, and then the mixture was stirred at 25 "C for 12 h under N2atmosphere. The reaction mixture was filtered and concentrated under reduced pressure. The residue was purified by column chromatography (Si02, PE/EtOAc = 5:1) to give 16 (1 .3 g, 51 %) as a yellow liquid.1H N R (400 MHz, DMSO-de) 8.55 (s, 1 H), 7.71-7.83 (m, 1 H), 7.54-7.51 (m, 1 H), 7.25 (d, J = 8.0 Hz, 1 H), 5.22-5.13 (m, 2H), 3.91 (t, J = 7.2 Hz, 1 H), 2.06-2.02 (m, 1 H), 1.38 (s, 9H), 0.87 (d, J - 6.4 Hz, 6H).

Reference： [1]Patent: WO2017/195069,2017,A1 .Location in patent: Page/Page column 61

25
[ 802325-29-7 ]
(5-fluoropyridin-2-yl)methyl (1-hydroxy-7-methyl-1,3-dihydrobenzo[c][1,2]oxaborole-6-carbonyl)-L-valinate hydrochloride [ No CAS ]

Reference： [1]Patent: WO2017/195069,2017,A1

26
[ 802325-29-7 ]
5-(4-chloro-1H-imidazol-2-yl)-1,3-dimethylpyridin-2(1H)-one [ No CAS ]
5-(4-chloro-1-((5-fluoropyridin-2-yl)methyl)-1H-imidazol-2-yl)-1,3-dimethylpyridin-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
17%		To a stirred solution of <strong>[802325-29-7](5-fluoropyridin-2-yl)methanol</strong> (45.5 mg, 0.358 mmol) in DMF (0.5 mL) at 0 C was added sodium hydride (10.73 mg, 0.447 mmol) and the reaction mixture stirred for 15 min prior to addition of 4-methylbenzene-l-sulfonyl chloride (85 mg, 0.447 mmol). The reaction was stirred for a further 30 min at this temperature. In a separate flask, 5-(4-chloro-lH-imidazol-2-yl)-l,3-dimethylpyridin-2(lH)-one (for an example preparation, see Intermediate 12, 40 mg, 0.179 mmol) was dissolved in DMF (0.5 mL) at 0 C, to which sodium hydride (8.58 mg, 0.358 mmol) was added and the reaction stirred for a further 30 min. The solution containing the tosylated pyridine was added dropwise to the flask containing the imidazole, and the reaction stirred for a further 16 h. The reaction was quenched with MeOH and the solvent removed in vacuo. The crude residue was dissolved in 1 : 1 DMSO: MeOH (0.9 mL) and purified by MDAP (Method C) to afford the title compound as a colourless solid (10.5 mg, 0.03 mmol, 17%). LCMS (System A): tRET = 0.77 min; MH+ 333, 335.

Reference： [1]Patent: WO2018/41964,2018,A1 .Location in patent: Page/Page column 94

27
[ 802325-29-7 ]
N-(4-amino-2-cyclopropyl-4-oxobutan-2-yl)-4-chloro-5-cyclopropylpicolinamide [ No CAS ]
N-(4-amino-2-cyclopropyl-4-oxobutan-2-yl)-5-cyclopropyl-4-[(5-fluoropyridin-2-yl)methoxy]pyridine-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
8%	With potassium tert-butylate; Potassium benzoate; In N,N-dimethyl-formamide; at 130℃; for 5h;Microwave irradiation;	Pottassium tert-butoxyde (13.9 mg, 124 imol) and potassium benzoate (19.9 mg, 124 imol) were added to a solution of N-(4-amino-2-cyclopropyl-4-oxobutan-2-yl)-4-chloro-5- cyclopropylpicolinamide (20 mg, 62.2 imol) and <strong>[802325-29-7](5-fluoropyridin-2-yl)methanol</strong> (9.48mg, 74.6 imol; CAN 802325-29-7) in DMF (500 iL). The reaction mixture was heated for5 h to 130 C in a microwave oven, poured onto ice / 0.1 N HC1 (25 mL) and extracted with EtOAc (2 x 50 mL). The combined extracts were washed with ice / brine (25 mL), dried over Na2SO4 and filtered. The filtrate was brought to dryness and the residue was purified by preparative TLC (silica gel, 2.0 mm, EtOAc) to obtain the title compound (2mg, 8%) as colorless liquid, LC-MS: 413.2 [MHi.

Reference： [1]Patent: WO2018/234284,2018,A1 .Location in patent: Page/Page column 33

28
[ 802325-29-7 ]
4-(2-((5-fluoropyridin-2-yl)methyl)-2H-tetrazol-5-yl)-N-(2-hydroxyethyl)benzenesulfonamide [ No CAS ]

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

29
[ 802325-29-7 ]
(4-(2-((5-fluoropyridin-2-yl)methyl)-2H-tetrazol-5-yl)-N-(2-hydroxyethyl)-2-methoxybenzenesulfonamide) [ No CAS ]

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

30
[ 802325-29-7 ]
(4-(1-((5-fluoropyridin-2-yl)methyl)-1H-1,2,3-triazol-4-yl)-N-(2-hydroxyethyl)benzene sulfonamide) [ No CAS ]

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

31
[ 802325-29-7 ]
4-(2-((5-fluoropyridin-2-yl)methyl)-2H-tetrazol-5-yl)-N-(2-hydroxyethyl)-2-methylbenzenesulfonamide [ No CAS ]

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

32
[ 802325-29-7 ]
4-(2-((5-fluoropyridin-2-yl)methyl)-2H-tetrazol-5-yl)-N-(2-hydroxyethyl)-3-methylbenzenesulfonamide [ No CAS ]

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

33
[ 802325-29-7 ]
2-fluoro-4-(2-((5-fluoropyridin-2-yl)methyl)-2H-tetrazol-5-yl)-N-(2-hydroxyethyl)benzenesulfonamide [ No CAS ]

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

34
[ 802325-29-7 ]
2-chloro-4-(2-((5-fluoropyridin-2-yl)methyl)-2H-tetrazol-5-yl)-N-(2-hydroxyethyl)benzenesulfonamide [ No CAS ]

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

35
[ 802325-29-7 ]
3-chloro-4-(2-((5-fluoropyridin-2-yl)methyl)-2H-tetrazol-5-yl)-N-(2-hydroxyethyl)benzenesulfonamide [ No CAS ]

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

36
[ 802325-29-7 ]
3-fluoro-4-(2-((5-fluoropyridin-2-yl)methyl)-2H-tetrazol-5-yl)-N-(2-hydroxyethyl)benzenesulfonamide [ No CAS ]

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

37
[ 802325-29-7 ]
2,3-difluoro-4-(2-((5-fluoropyridin-2-yl)methyl)-2H-tetrazol-5-yl)-N-(2-hydroxyethyl)benzenesulfonamide [ No CAS ]

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

38
[ 802325-29-7 ]
2,6-difluoro-4-(2-((5-fluoropyridin-2-yl)methyl)-2H-tetrazol-5-yl)-N-(2-hydroxyethyl)benzenesulfonamide [ No CAS ]

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

39
[ 802325-29-7 ]
2-fluoro-4-(2-((5-fluoropyridin-2-yl)methyl)-2H-tetrazol-5-yl)-N-(2-hydroxyethyl)-5-methylbenzenesulfonamide [ No CAS ]

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

40
[ 802325-29-7 ]
C₁₆H₁₇FN₆O₃S [ No CAS ]

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

41
[ 802325-29-7 ]
4-(2-((5-fluoropyridin-2-yl)methyl)-2H-tetrazol-5-yl)benzenesulfonamide [ No CAS ]

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

42
[ 802325-29-7 ]
tert-butyl(cyanomethyl)((4-(2-((5-fluoropyridin-2-yl)methyl)-2H-tetrazol-5-yl)phenyl)sulfonyl)carbamate [ No CAS ]

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

43
[ 802325-29-7 ]
2-(azidomethyl)-5-fluoropyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%		To a stirred solution of <strong>[802325-29-7](5-fluoropyridin-2-yl)methanol</strong> (500 mg, 3.937 mmol, commercial source: Combi-Blocks) and triethylamine (398 mg, 3.937 mmol) in /V,/V-dimethylformamide (10 ml_), mesyl chloride (451 mg, 3.937 mmol) was added at 27 C. The reaction mixture was stirred at 27 C for 2 h. Followed by the addition of sodium azide (384 mg, 5.905 mmol) at 27 C and the reaction mixture was stirred for 12 h at the same temperature. Upon completion, the reaction mixture was concentrated under reduced pressure. The crude compound was purified by column chromatography (silica gel 100-200 mesh) using 5% ethyl acetate in pet ether. The pure fractions were collected and concentrated under reduced pressure to afford 2-(azidomethyl)-5- fluoropyridine (150 mg, 25%) as a brown liquid. NMR (400 MHz, CDCI3) 5 8.46 (d, J = 2.6 Hz, 1 H), 7.47-7.40 (m, 1 H), 7.39-7.33 (m, 1 H), 4.48 (s, 2H). MS m/z [M+H]+= 153.12.

Reference： [1]Patent: WO2019/34729,2019,A1 .Location in patent: Page/Page column 62

44
[ 802325-29-7 ]
2-(bromomethyl)-5-fluoropyridine hydrobromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With phosphorus tribromide; In dichloromethane; at 26℃; for 3h;	To a stirred solution of <strong>[802325-29-7](5-fluoropyridin-2-yl)methanol</strong> (600 mg, 4.7244 mmol, commercial source: Combi-Blocks) in dichloromethane (15 mL), phosphorus tribromide (1.5 mL) was added at 0 C. The reaction mixture was allowed to stir at 26 C for 3 h. On completion, the reaction mixture was concentrated under reduced pressure to afford 2-(bromomethyl)-5- fluoropyridine hydrobromide (1 .7 g) as a yellow solid.1H NMR (400 MHz, DMSO-c/6) +=190.09. The compound was used for next step without any further purification.

Reference： [1]Patent: WO2019/34729,2019,A1 .Location in patent: Page/Page column 34

45
[ 802325-29-7 ]
4-(1-((5-fluoropyridin-2-yl)methyl)-1H-1,2,3-triazol-4-yl)benzenesulfonamide [ No CAS ]

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

46
[ 802325-29-7 ]
tert-butyl (cyanomethyl)((4-(1-((5-fluoropyridin-2-yl)methyl)-1 H-1,2,3-triazol-4-yl)phenyl)sulfonyl)carbamate [ No CAS ]

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

47
[ 802325-29-7 ]
3-(3-((6-fluoropyridin-3-yl)methyl)isoxazol-5-yl)pyridin-2-amine [ No CAS ]
3-(3-((6-((5-fluoropyridin-2-yl)methoxy)pyridin-3-yl)methyl)isoxazol-5-yl)pyridin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	With potassium tert-butylate; In tetrahydrofuran; for 0.5h;	To a neat mixture of 3-(3-((6-fluoropyridin-3-yl)methyl)isoxazol-5-yl)pyridin-2 -amine (Intermediate E, 50 mg, O. l9mmol) and 5-fluoropyridin-2-yl)methanol (2l2mg, l.67mmol) was added potassium 2-methylpropane-2-olate (1M in THF, l.85mL, l.85mmol) and the mixture was stirred for 30min. The mixture was transferred to a silica gel samplet which was subsequently loaded on to a Biotage Snap column. The residue was purified by column chromatography (Si02, hexane/ethyl acetate). Combined fractions were concentrated under reduced pressure. Residue was dissolved in acetonitrile (5mL) and water (lOmL), frozen and lyophilized to yield 3-(3-((6-((5-fluoropyridin-2- yl)methoxy)pyridin-3-yl)methyl)isoxazol-5-yl)pyridin-2-amine (2lmg, 0.056mmol, 30%) as a white solid. MS: 378.0 [M+H]+.

Reference： [1]Patent: WO2019/113542,2019,A1 .Location in patent: Paragraph 0437; 0438

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 802325-29-7 ] {[proInfo.proName]}

Quality Control of [ 802325-29-7 ]

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Product Details of [ 802325-29-7 ]

Safety of [ 802325-29-7 ]

Application In Synthesis of [ 802325-29-7 ]

[ 802325-29-7 ] Synthesis Path-Upstream 1~4

[ 802325-29-7 ] Synthesis Path-Downstream 1~47

Related Functional Groups of [ 802325-29-7 ]

Fluorinated Building Blocks

Alcohols

Related Parent Nucleus of [ 802325-29-7 ]

Pyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 802325-29-7 ]

Related Parent Nucleus of
[ 802325-29-7 ]