[ CAS No. 182924-36-3 ] {[proInfo.proName]}

Name: 182924-36-3|5-(Bromomethyl)-2-chloropyridine|98%
Brand: Ambeed
SKU: A260649
Price: 23.0 USD
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Quality Control of [ 182924-36-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 182924-36-3 ]

SDS Specification

Alternatived Products of [ 182924-36-3 ]

Product Details of [ 182924-36-3 ]

CAS No. :	182924-36-3	MDL No. :	MFCD07368893
Formula :	C₆H₅BrClN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YJOULMMJZAADRY-UHFFFAOYSA-N
M.W :	206.47	Pubchem ID :	6424661
Synonyms :

Calculated chemistry of [ 182924-36-3 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.17
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	42.08
TPSA :	12.89 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.88 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.97
Log Po/w (XLOGP3) :	2.37
Log Po/w (WLOGP) :	2.48
Log Po/w (MLOGP) :	1.91
Log Po/w (SILICOS-IT) :	3.01
Consensus Log Po/w :	2.35

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.04
Solubility :	0.188 mg/ml ; 0.000911 mol/l
Class :	Soluble
Log S (Ali) :	-2.28
Solubility :	1.08 mg/ml ; 0.00523 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.9
Solubility :	0.0258 mg/ml ; 0.000125 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.98

Safety of [ 182924-36-3 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	1759
Hazard Statements:	H314	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 182924-36-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 182924-36-3 ]
Downstream synthetic route of [ 182924-36-3 ]

[ 182924-36-3 ] Synthesis Path-Upstream 1~6

1
[ 182924-36-3 ]
[ 23100-12-1 ]

Reference： [1] Synthetic Communications, 2010, vol. 40, # 8, p. 1106 - 1114

2
[ 21543-49-7 ]
[ 182924-36-3 ]

Yield	Reaction Conditions	Operation in experiment
85%	With carbon tetrabromide; triphenylphosphine In dichloromethane at 0 - 20℃; for 4.75 h; Inert atmosphere	Synthesis 265-(Bromomethyl)-2-chloropyridine (26).To a solution of (6-chloropyridin-3-yl)methanol (1 .005 g, 7.0 mmol, 1 eq) in dry DCM(20 ml.) CBr₄ (99percent, 2.885 g, 8.6 mmol, 1 .2 eq) was added. This solution was cooled to 0°C and then Ph₃P (2.297 g, 8.7 mmol, 1 .2 eq) was added. The reaction mixture was stirred at 0°C for 15 minutes under nitrogen atmosphere and then it was allowed to warm to room temperature. After 4.5 hours the reaction mixture was treated with 20 ml. of water and extracted with DCM. The combined organic extracts were dried over anhydrous Na₂S0₄, filtered and the solvent was removed in vacuo. The residue was purified by flash chromatography on silica gel (n-Hex/EtOAc 9: 1 ) to afford 1 .231 g of 26 as white solid (85percent).0.33 (n-Hex/EtOAc 9:1 ). ¹ H NMR (400 MHz, CDCI₃) δ 8.40 (d, J = 2.5 Hz, 1 H), 7.70 J = 8.2, 2.6 Hz, 1 H), 7.33 (d, J = 8.3 Hz, 1 H), 4.44 (s, 2H); ¹³C NMR (100 MHz, CDCI₃) 5 151.4, 149.6, 139.5, 132.8, 124.6, 28.5; ESI MS m/z: calcd. for C₆H₆BrCIN [/W+H]⁺ 205.9, found: 205.9, 207.9, 209.9.
76.65%	With phosphorus tribromide In dichloromethane at 0 - 20℃; for 3 h;	To a stirred solution of (6-chloropyridin-3-yl)methanol (2 g, 13.93 mmol) in dry DCM (40 ml), PBr3 (1.6 ml, 16.71 mmol) was added dropwise at 0°C. The reaction mixture was stirred at ambient temperature for 3h. The progress of the reaction was monitored by TLC (3:7, Ethyl acetate: pet. ether). After completion of the reaction the reactionmixture was cooled o room temperature and quenched with aqueous 10percent NaHCO3 solution (30 ml) and extracted with DCM (3 X 50 ml). The combined organic layer was dried over anhydrous sodium sulfate and removed under reduced pressure. The crude was purified by column chromatography (60-120 mesh silica gel) using 8percent Ethyl acetate in pet ether as eluent to yield pure 5-(bromomethyl)-2-chloropyridine (2.2 g,76.65percent) as a yellow oil.
62%	With carbon tetrabromide; 1,3-bis-(diphenylphosphino)propane In dichloromethane	(6-chloro-3-pyridinyl)-methanol (1.0 eq.) was taken up in dichloromethane and stirred overnight with carbon tetrabromide (1.5 eq.) and 1,3-bis(diphenylphosphino)propane (0.75 eq.) Ether was added to the solution and filtration followed by concentration of the filtrate afforded (6-chloro-3-bromomethyl) pyridine in 62percent yield.

62%	With carbon tetrabromide; 1,3-bis-(diphenylphosphino)propane In dichloromethane	(6-Chloro-3-pyridinyl)-methanol (1.0 eq.) was taken up in dichloromethane and stirred overnight with carbon tetrabromide (1.5 eq.) and 1,3-bis(diphenylphosphino)propane (0.75 eq.). Ether was added to the solution and filtration followed by concentration of the filtrate afforded (6-chloro-3-bromomethyl)pyridine in 62percent yield.
60%	With carbon tetrabromide; triphenylphosphine In dichloromethane at 0 - 20℃; for 16 h;	To a solution of 19-3B (115 mg, 0.804 mmol) in DCM (3 mL) was added carbon tetrabromide (320 mg, 0.965 mmol), triphenylphosphine (210 mg, 0.965 mmol), and stirred at 0 °C to RT for 16 hr. The reaction mixture was diluted with excess DCM (20 mL), washed with water (20 mL), brine (10 mL) and dried over Na₂S0₄, and the organic phase was concentrated under reduced pressure. Obtained crude compound was purified using silica gel chromatography (8percent EtOAc in hexanes) to afford 19- 4B (100 mg, 0.48 mmol, yield 60percent). MS (ESI): m/z 206.0 (M-l)⁺.
0.49 g	With phosphorus tribromide In dichloromethane at 0 - 30℃; for 1.5 h; Inert atmosphere	To a solution of 2-chloro-5-hydroxymethylpyridine (0.45 g, 0.003 mole) in DCM (10 mL) at 0 °C under N₂, was added phosphorus tribromide (0.44 mL, 0.0037 mole) drop wise. Reaction mixture was warmed to RT and stirred for 1.5 hours. The reaction mixture was diluted with DCM (75 mL), treated with saturated aqueous sodium bicarbonate (20 mL). Organic layer was washed with water (20 mL), brine solution (20 mL) and dried over Na₂S0₄ and concentrated under vacuum to obtain the title compound. Yield: 0.49 g; ^lH - NMR (CDC1₃, 400 MHz) δ ppm: 4.35 (s, 2H), 7.32 - 7.34 (d, J = 8.2 Hz, 1H), 7.69 - 7.71 (dd, J = 2.2, 7.9 Hz, 1H), 8.40 - 8.41 (d, J = 1.7 Hz, 1H); Mass (m/z): 205.9, 208.0 (M+H)⁺.

Reference： [1] Tetrahedron Letters, 2009, vol. 50, # 16, p. 1765 - 1767
[2] Patent: WO2013/38153, 2013, A1, . Location in patent: Page/Page column 93-94
[3] Patent: WO2016/97345, 2016, A1, . Location in patent: Page/Page column 14; 15
[4] Patent: US2004/82785, 2004, A1, . Location in patent: Page 21
[5] Patent: US2008/9485, 2008, A1, . Location in patent: Page/Page column 24
[6] Patent: WO2016/154241, 2016, A1, . Location in patent: Paragraph 578; 583
[7] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 23, p. 6120 - 6123
[8] Patent: WO2018/42362, 2018, A1, . Location in patent: Page/Page column 40

3
[ 18368-64-4 ]
[ 182924-36-3 ]

Yield	Reaction Conditions	Operation in experiment
31%	With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethaneReflux	Example 2. Synthesis of compound 1-1. Into a 1000-mL round-bottom flask, was placed 2-chloro-5-methylpyridine (44 g, 344.83 mmol, 1.00 equiv), perchloromethane (500 mL), 1- bromopyrrolidine-2,5-dione (60 g, 337.08 mmol, 0.98 equiv), and benzoic peroxyanhydride (1 g). The resulting solution was heated to reflux for overnight. The solids were removed by Alteration. The filtrate was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1 :20). This resulted in 22 g (31percent) of 5- (bromomethyl)-2-chloropyridine as a white solid.LC-MS: (ES, m/z): 208 [M+H]⁺

Reference： [1] European Journal of Organic Chemistry, 2015, vol. 2015, # 8, p. 1764 - 1770
[2] Patent: WO2013/3505, 2013, A1, . Location in patent: Page/Page column 54; 55
[3] Patent: WO2004/56365, 2004, A2, . Location in patent: Page/Page column 129
[4] Patent: US2011/9390, 2011, A1, . Location in patent: Page/Page column 20
[5] Patent: WO2008/62182, 2008, A1, . Location in patent: Page/Page column 143-144

4
[ 22536-61-4 ]
[ 182924-36-3 ]

Yield	Reaction Conditions	Operation in experiment
38%	With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 6 h; Reflux	Synthesis Example 25 N-[1-((2-chloropyrimidin-5-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide (Compound 243) 2-chloro-5-methylpyrimidine (1.04 g, 8.13 mmol) was dissolved in 30 mL of carbon tetrachloride, 1.73 g (9.75 mmol) of N-bromosuccinimide and 20 mg of benzoyl peroxide were added, and the mixture was refluxed under heating for 6 hours. Following reaction completion, the reaction mixture was returned to room temperature, concentrated under reduced pressure, and purified by silica gel column chromatography (hexane/ethyl acetate=3:1), affording 641 mg of 5-bromomethyl-2-chloropyridine (yield, 38percent). ¹H-NMR (CDCl₃, δ, ppm): 4.42 (2H, s), 8.66 (2H, s)

Reference： [1] Patent: US2013/150414, 2013, A1, . Location in patent: Paragraph 0437

5
[ 49608-01-7 ]
[ 182924-36-3 ]

Reference： [1] Patent: WO2016/154241, 2016, A1,

6
[ 5326-23-8 ]
[ 182924-36-3 ]

Reference： [1] Patent: WO2018/42362, 2018, A1,

[ 182924-36-3 ] Synthesis Path-Downstream 1~57

2
[ 16874-34-3 ]
[ 182924-36-3 ]
[ 919361-16-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 6120 - 6123

3
[ 21543-49-7 ]
[ 182924-36-3 ]

Yield	Reaction Conditions	Operation in experiment
85%	With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0 - 20℃; for 4.75h;Inert atmosphere;	Synthesis 265-(Bromomethyl)-2-chloropyridine (26).To a solution of (6-chloropyridin-3-yl)methanol (1 .005 g, 7.0 mmol, 1 eq) in dry DCM(20 ml.) CBr4 (99%, 2.885 g, 8.6 mmol, 1 .2 eq) was added. This solution was cooled to 0C and then Ph3P (2.297 g, 8.7 mmol, 1 .2 eq) was added. The reaction mixture was stirred at 0C for 15 minutes under nitrogen atmosphere and then it was allowed to warm to room temperature. After 4.5 hours the reaction mixture was treated with 20 ml. of water and extracted with DCM. The combined organic extracts were dried over anhydrous Na2S04, filtered and the solvent was removed in vacuo. The residue was purified by flash chromatography on silica gel (n-Hex/EtOAc 9: 1 ) to afford 1 .231 g of 26 as white solid (85%).0.33 (n-Hex/EtOAc 9:1 ). 1 H NMR (400 MHz, CDCI3) delta 8.40 (d, J = 2.5 Hz, 1 H), 7.70 J = 8.2, 2.6 Hz, 1 H), 7.33 (d, J = 8.3 Hz, 1 H), 4.44 (s, 2H); 13C NMR (100 MHz, CDCI3) 5 151.4, 149.6, 139.5, 132.8, 124.6, 28.5; ESI MS m/z: calcd. for C6H6BrCIN [/W+H]+ 205.9, found: 205.9, 207.9, 209.9.
76.65%	With phosphorus tribromide; In dichloromethane; at 0 - 20℃; for 3h;	To a stirred solution of (6-chloropyridin-3-yl)methanol (2 g, 13.93 mmol) in dry DCM (40 ml), PBr3 (1.6 ml, 16.71 mmol) was added dropwise at 0C. The reaction mixture was stirred at ambient temperature for 3h. The progress of the reaction was monitored by TLC (3:7, Ethyl acetate: pet. ether). After completion of the reaction the reactionmixture was cooled o room temperature and quenched with aqueous 10% NaHCO3 solution (30 ml) and extracted with DCM (3 X 50 ml). The combined organic layer was dried over anhydrous sodium sulfate and removed under reduced pressure. The crude was purified by column chromatography (60-120 mesh silica gel) using 8% Ethyl acetate in pet ether as eluent to yield pure 5-(bromomethyl)-2-chloropyridine (2.2 g,76.65%) as a yellow oil.
62%	With carbon tetrabromide; 1,3-bis-(diphenylphosphino)propane; In dichloromethane;	(6-chloro-3-pyridinyl)-methanol (1.0 eq.) was taken up in dichloromethane and stirred overnight with carbon tetrabromide (1.5 eq.) and 1,3-bis(diphenylphosphino)propane (0.75 eq.) Ether was added to the solution and filtration followed by concentration of the filtrate afforded (6-chloro-3-bromomethyl) pyridine in 62% yield.

62%	With carbon tetrabromide; 1,3-bis-(diphenylphosphino)propane; In dichloromethane;	(6-Chloro-3-pyridinyl)-methanol (1.0 eq.) was taken up in dichloromethane and stirred overnight with carbon tetrabromide (1.5 eq.) and 1,3-bis(diphenylphosphino)propane (0.75 eq.). Ether was added to the solution and filtration followed by concentration of the filtrate afforded (6-chloro-3-bromomethyl)pyridine in 62% yield.
60%	With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0 - 20℃; for 16h;	To a solution of 19-3B (115 mg, 0.804 mmol) in DCM (3 mL) was added carbon tetrabromide (320 mg, 0.965 mmol), triphenylphosphine (210 mg, 0.965 mmol), and stirred at 0 C to RT for 16 hr. The reaction mixture was diluted with excess DCM (20 mL), washed with water (20 mL), brine (10 mL) and dried over Na2S04, and the organic phase was concentrated under reduced pressure. Obtained crude compound was purified using silica gel chromatography (8% EtOAc in hexanes) to afford 19- 4B (100 mg, 0.48 mmol, yield 60%). MS (ESI): m/z 206.0 (M-l)+.
0.49 g	With phosphorus tribromide; In dichloromethane; at 0 - 30℃; for 1.5h;Inert atmosphere;	To a solution of 2-chloro-5-hydroxymethylpyridine (0.45 g, 0.003 mole) in DCM (10 mL) at 0 C under N2, was added phosphorus tribromide (0.44 mL, 0.0037 mole) drop wise. Reaction mixture was warmed to RT and stirred for 1.5 hours. The reaction mixture was diluted with DCM (75 mL), treated with saturated aqueous sodium bicarbonate (20 mL). Organic layer was washed with water (20 mL), brine solution (20 mL) and dried over Na2S04 and concentrated under vacuum to obtain the title compound. Yield: 0.49 g; lH - NMR (CDC13, 400 MHz) delta ppm: 4.35 (s, 2H), 7.32 - 7.34 (d, J = 8.2 Hz, 1H), 7.69 - 7.71 (dd, J = 2.2, 7.9 Hz, 1H), 8.40 - 8.41 (d, J = 1.7 Hz, 1H); Mass (m/z): 205.9, 208.0 (M+H)+.

Reference： [1]Tetrahedron Letters,2009,vol. 50,p. 1765 - 1767
[2]Patent: WO2013/38153,2013,A1 .Location in patent: Page/Page column 93-94
[3]Patent: WO2016/97345,2016,A1 .Location in patent: Page/Page column 14; 15
[4]Patent: US2004/82785,2004,A1 .Location in patent: Page 21
[5]Patent: US2008/9485,2008,A1 .Location in patent: Page/Page column 24
[6]Patent: WO2016/154241,2016,A1 .Location in patent: Paragraph 578; 583
[7]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 6120 - 6123
[8]Patent: WO2018/42362,2018,A1 .Location in patent: Page/Page column 40

4
[ 306296-78-6 ]
[ 182924-36-3 ]
C₂₂H₃₅ClN₄O₂ [ No CAS ]

Reference： [1]Patent: US6391865,2002,B1 .Location in patent: Page column 65-66

5
[ 478964-94-2 ]
[ 182924-36-3 ]
[ 717105-13-0 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,3-dimethyl-2-imidazolidinone; potassium carbonate; at 60℃; for 2h;	To a solution of 323 mg (1.10 mmol) of (2-AMINO-5-PROPARGYLOXY-PHENYL)-4- isopropyl-phenyl) -methanone and 250 mg (1.21 mmol) of 2-bromomethyl-2-chloro- pyridine (step A) in 2 ml 1, 3-dimethyl-2-imidazolidinone (DMEU) 213 mg (1.54 mmol) of potassium carbonate are added. The reaction is complete after stirring for 2 h at 60 C. The cooled yellow suspension is distributed between ethyl acetate and bicarbonate solution. Flash chromatography (hexane/ethyl acetate) affords a yellow solid. m. p. 96 C. 'H-NMR (300 MHz, CDC13) : 8.49 (t, 1H), 8.40 (d, 1H), 7.67 (dd, 1H), 7.61 (d, 2H), 7.31 (d, 2H), 7.30 (d, 1H), 7.23 (d, 1H), 7.08 (dd, 1H), 6.59 (d, 1H), 4.53 (d, 2H), 4.48 (d, 2H), 2.99 (HEPT, 1H), 2.48 (t, 1H), 1.31 (d, 6H). MS: 419 (M+L)

Reference： [1]Patent: WO2004/56365,2004,A2 .Location in patent: Page/Page column 129-130

6
[ 18368-64-4 ]
[ 182924-36-3 ]

Yield	Reaction Conditions	Operation in experiment
31%	With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane;Reflux;	Example 2. Synthesis of compound 1-1. Into a 1000-mL round-bottom flask, was placed 2-chloro-5-methylpyridine (44 g, 344.83 mmol, 1.00 equiv), perchloromethane (500 mL), 1- bromopyrrolidine-2,5-dione (60 g, 337.08 mmol, 0.98 equiv), and benzoic peroxyanhydride (1 g). The resulting solution was heated to reflux for overnight. The solids were removed by Alteration. The filtrate was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1 :20). This resulted in 22 g (31%) of 5- (bromomethyl)-2-chloropyridine as a white solid.LC-MS: (ES, m/z): 208 [M+H]+
	With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 17h;Heating / reflux;	A solution of 1.28 g (10.0 mmol) 2-chloro-5-methyl-pyridine in 25 ML carbon tetra- chloride is treated with 1.79 g (10.0 mmol) of freshly recrystallised N-bromo- succinimid and 30 mg benzoyl peroxide. The mixture is heated to reflux for 17 h and filtered. The filtrate is washed with water and concentrated. Flash chromatography (HEXANE/ETHYL acetate) results in a white low melting solid. m. p. 40-43 C. MS: 210 (2), 208 (100), 206 (75) (chloro-bromo isotope pattern) (M+1) +
	With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 1.5h;Reflux;	Reference Example 54; 4-(6-chloro-pyridin-3-yl-methyl)-morpholine; a) Preparation of 5-bromomethyl-2-chloro-pyridine; N-bromosuccinimide (6.1 g, 3.44 mmol) and benzoyl peroxide (218 mg, 0.09 mmol) were added successively to a solution of 2-chloro-5-methyl-pyridine (4.0 g, 3.13 mmol) in carbon tetrachloride (20 mL) and refluxed for 90 min. The reaction mixture was cooled to room temperature, water added and the organic layer separated. The organic layer was washed successively with water, brine, dried over anhydrous sodium sulfate and filtered. The resultant solution of 5-bromomethyl-2-chloro-pyridine was used as such for the next step.

With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 1.5h;Heating / reflux;

a) Preparation of 5-bromomethyl-2-chloro-pyridine. N-bromosuccinimide (6.1 g, 3.44 mmol) and benzoyl peroxide (218 mg, 0.09 mmol) were added successively to a solution of 2-chloro-5-methyl-pyridine (4.0 g, 3.13 mmol) in carbon tetrachloride (20 mL) and refluxed for 90 min. The reaction mixture was cooled to room temperature, water added and the organic layer separated. The organic layer was washed successively with water, brine, dried over anhydrous sodium sulfate and filtered. The resultant solution of 5-bromomethyl-2-chloro-pyridine was used as such for the next step.

Reference： [1]European Journal of Organic Chemistry,2015,vol. 2015,p. 1764 - 1770
[2]Patent: WO2013/3505,2013,A1 .Location in patent: Page/Page column 54; 55
[3]Patent: WO2004/56365,2004,A2 .Location in patent: Page/Page column 129
[4]Patent: US2011/9390,2011,A1 .Location in patent: Page/Page column 20
[5]Patent: WO2008/62182,2008,A1 .Location in patent: Page/Page column 143-144

7
[ 1606-49-1 ]
[ 182924-36-3 ]
[ 371122-24-6 ]

Yield	Reaction Conditions	Operation in experiment
221 mg (yield; 35.2%)	With potassium hydroxide; In ethanol; toluene; acetonitrile;	1-(6-chloro-3-pyridyl)methyl-1,4,5,6-tetrahydropyrimidine [Compound 27] To an ice-cooled solution of 384 mg (4.6 mmol) of 1,4,5,6-tetrahydropyrimidine in 5 ml of acetonitrile was added 619 mg (3 mmol) of <strong>[182924-36-3]5-bromomethyl-2-chloropyridine</strong>, and the mixture was stirred for 15 minutes. After removal of solvent under reduced pressure, 6 ml of the solution of 0.5N potassium hydroxide in ethanol was added to the residue. The insoluble matter was removed off by filtration, and the filtrate was concentrated under reduced pressure. The resulting residue was dissolved in toluene, and the solvent was removed again under reduced pressure. The resulting residue was purified by aminopropyl-coated silica gel (Chromatorex NH-type; Fuji Silysia Chemical Ltd.) column chromatography (eluent; dichloromethane:methanol=40:1) to give 221 mg (yield; 35.2%) of 1-(6-chloro-3-pyridyl)methyl-1,4,5,6-tetrahydropyrimidine as colorless oil.

Reference： [1]Patent: US2003/100769,2003,A1

8
[ 10416-81-6 ]
ether-isopropyl ether [ No CAS ]
[ 182924-36-3 ]
3-(6-chloro-pyridin-3-yl)methyl-2-[(6-chloro-pyridin-3-yl)methyl]imino-4-methyl-2,3-dihydrothiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
310 mg (yield; 42.4%)	In acetonitrile;	3-(6-Chloro-3-pyridyl)methyl-2-[(6-chloro-3-pyridyl)methyl]imino-4-methyl-2,3-dihydrothiazole [Compound 9] A mixture of 228 mg (2 mmol) of 2-amino-4-methylthiazoline and 1.03 g (5 mmol) of <strong>[182924-36-3]5-bromomethyl-2-chloropyridine</strong> in 30 ml of acetonitrile was heated for 8 hours at 90 C. under refluxing. Then, the reaction mixture was cooled to the room temperature, and the solvent was removed under reduced pressure. The resulting residue was mixed with dichloromethane and saturated sodium hydrogen carbonate aqueous solution, and the organic layer was separated. The water layer was extracted with dichloromethane, and combined organic layer was dried over magnesium sulfate. The solvent was removed under reduced pressure and the resulting residue was purified by silica gel 60 (Merck Co., Ltd.) column chromatography (eluent; dichloromethane: ethyl acetate=from 9:1 to 4:1) to give 600 mg (yield; 82.1%) of crude product as yellow oil. Then, this crude product was purified again by aminopropyl-coated silica gel (Chromatorex NH-type; Fuji Silysia Chemical Ltd.) column chromatography (eluent; dichloromethane), and the eluted product was crystallized by treatment with ether-isopropyl ether to give 310 mg (yield; 42.4%) of 3-(6-chloro-3-pyridyl)methyl-2-[(6-chloro-3-pyridyl)methyl]imino-4-methyl-2,3-dihydrothiazole as milky white crystalline. 200 mg (0.548 mmol) of this product was dissolved in methanol and to this solution was added 64 mg (0.551 mmol) of fumaric acid, and the mixture was concentrated under reduced pressure.

Reference： [1]Patent: US2003/78259,2003,A1

9
[ 33142-18-6 ]
[ 182924-36-3 ]
3-(6-chloro-pyridin-3-yl)methyl-2-phenylimino-2,3-dihydrothiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57 mg (yield; 18.9%)	In acetonitrile;	3-(6-Chloro-3-pyridyl)methyl-2-phenylimino-2,3-dihydrothiazole [Compound 12] A mixture of 176 mg (1 mmol) of 2-anilinothiazole and 227 mg (1.1 mmol) of <strong>[182924-36-3]5-bromomethyl-2-chloropyridine</strong> in 10 ml of acetonitrile was heated for 15 hours at 90 C. under refluxing. Then, the reaction mixture was cooled to the room temperature, and the solvent was removed under reduced pressure. The resulting residue was mixed with dichloromethane and saturated sodium hydrogen carbonate aqueous solution, and the organic layer was separated. The water layer was extracted with dichloromethane, and combined organic layer was dried over magnesium sulfate. The solvent was removed under reduced pressure and the resulting residue was purified by silica gel 60 (Merck Co., Ltd.) column chromatography (eluent; dichloromethane: ethyl acetate=from 30:1 to 9:1) to give 57 mg (yield; 18.9%) of 3-(6-chloro-3-pyridyl)methyl-2-phenylimino-2,3-dihydrothiazole as yellow crystalline and 240 mg of mixture product of 3-(6-chloro-3-pyridyl)methyl-2-phenylimino-2,3-dihydrothiazole and 2-anilino-thiazole.

Reference： [1]Patent: US2003/78259,2003,A1

10
[ 182924-36-3 ]
[ 619-08-9 ]
2-chloro-5-(2-chloro-4-nitrophenoxy)methylpyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran;	EXAMPLE 5 2-Chloro-4-nitrophenol (17.4 mmol) in 15 ml of THF is slowly added to a stirring suspension of sodium hydride (17.4 mmol) in 25 ml of THF. After gas evolution has ceased, 2-chloro-5-bromomethylpyridine is added and the mixture is heated under reflux overnight. The reaction is diluted with water, extracted with chloroform, washed with water, dried and stripped to give 2-chloro-5-(2-chloro-4-nitrophenoxy)methylpyridine.

Reference： [1]Patent: US4332944,1982,A

11
[ 110-91-8 ]
[ 182924-36-3 ]
[ 311774-34-2 ]

Yield	Reaction Conditions	Operation in experiment
21%	In tetrachloromethane; at 20℃; for 6h;	b) Preparation of 4-(6-chloro-pyridin-3-yl-methyl)-morpholine. Morpholine (7.0 g, 8.8 mmol) was added to the solution of 5-bromomethyl-2- chloro-pyridine in carbon tetrachloride (20 mL) and stirred at room temperature for 6 h. Water was-added to the reaction, mixture and the separated organic layer was washed with water, brine, dried O.ver anhydrous sodium sulfate, filtered and concentrated to afford the crude product. Purification by column chromatography using silica gel (60- 120 mesh) and ethyl acetate as eluent afforded 4-(6-chloro-pyridin-3-yl-methyl)- morpholine (1.2 g, 21 %) as a brown oily liquid.
	In tetrachloromethane; at 20℃; for 6h;	b) Preparation of 4-(6-chloro-pyridin-3-yl-methyl)-morpholine; Morpholine (7.0 g, 8.8 mmol) was added to the solution of <strong>[182924-36-3]5-bromomethyl-2-chloro-pyridine</strong> in carbon tetrachloride (20 mL) and stirred at room temperature for 6 h. Water was added to the reaction mixture and the separated organic layer was washed with water, brine, dried over anhydrous sodium sulfate, filtered and concentrated to afford the crude product. Purification by column chromatography using silica gel (60-120 mesh) and ethyl acetate as eluent afforded 4-(6-chloro-pyridin-3-yl-methyl)-morpholine (1.2 g, 21%) as a brown oily liquid.

Reference： [1]Patent: WO2008/62182,2008,A1 .Location in patent: Page/Page column 144
[2]Patent: US2011/9390,2011,A1 .Location in patent: Page/Page column 20

12
[ 182924-36-3 ]
[ 17639-76-8 ]
[ 1145669-84-6 ]

Reference： [1]Tetrahedron Letters,2009,vol. 50,p. 1765 - 1767

13
[ 182924-36-3 ]
[ 6078-17-7 ]
[ 1172120-81-8 ]

Reference： [1]European Journal of Medicinal Chemistry,2009,vol. 44,p. 3293 - 3298

14
[ 182924-36-3 ]
[ 23100-12-1 ]

Reference： [1]Synthetic Communications,2010,vol. 40,p. 1106 - 1114

15
[ 182924-36-3 ]
[ 1227924-69-7 ]

Yield	Reaction Conditions	Operation in experiment
40%	With tris(tetra-n-butylammonium) hydrogen pyrophosphate; In acetonitrile;	(6-Chloropyridin-3-yl)-methyl-diphosphate (BPH-1029). 5-(Bromomethyl)-2- chloropyridine (103 mg, 0.5 mmol) was treated with 1.35 g (1.5 mmol) tris(tetra-n- butylammonium) hydrogen diphosphate in CH3CN (4 mL). Flash chromatography on a cellulose column ( 3: 2 (v/v) 2-propanol/50 mM NH4HCO3) yielded 70 mg (40 %) of a white solid. LH NMR (400 MHz, D20): delta 4.82 (d, JH,P = 7.6 Hz, 2H), 7.29 (d, J = 8.4 Hz, 1H), 7.74 (dd, J = 8.4 Hz, J = 2.4 Hz, 1H), 8.20 (d, J = 2.4 Hz, 1H). 31P NMR (162 MHz, D20) : delta -9.73 (d, J = 22.0 Hz), -5.81 (d, J = 22.0 Hz).

Reference： [1]Journal of the American Chemical Society,2010,vol. 132,p. 6719 - 6727
[2]Patent: WO2011/44505,2011,A2 .Location in patent: Page/Page column 29

16
[ 182924-36-3 ]
[ 169037-23-4 ]
[ 1247778-14-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 5617 - 5622

17
[ 947144-42-5 ]
[ 182924-36-3 ]
[ 1338370-95-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5939 - 5943

18
[ 182924-36-3 ]
[ 1417421-43-2 ]

Reference： [1]Patent: WO2013/3505,2013,A1

19
[ 182924-36-3 ]
[ 1417421-42-1 ]

Reference： [1]Patent: WO2013/3505,2013,A1

20
[ 182924-36-3 ]
[ 828-27-3 ]
[ 1417421-41-0 ]

Yield	Reaction Conditions	Operation in experiment
77%	With potassium carbonate; In acetonitrile;Reflux;	Example 3. Synthesis of compound 1-2. Into a 1000-mL round-bottom flask, was placed <strong>[182924-36-3]5-(bromomethyl)-2-chloropyridine</strong> (22 g, 106.54 mmol, 1.00 equiv), 4- (trifluoromethoxy)phenol (22 g, 123.53 mmol, 1.16 equiv), acetonitrile (300 mL), and potassium carbonate (22 g, 159.19 mmol, 1.49 equiv). The resulting solution was heated at reflux overnight. The resulting mixture was concentrated under vacuum. The residue was dissolved in 300 mL of dichloromethane. The solids were removed by filtration. The filtrate was concentrated under vacuum. This resulted in 25 g (77%) of 2-chloro-5-((4- (trifluoromethoxy)phenoxy)methyl)pyridine as a light yellow solid.LC-MS: (ES, m/z): 304 [M+H]+

Reference： [1]Patent: WO2013/3505,2013,A1 .Location in patent: Page/Page column 55

21
[ 182924-36-3 ]
[ 133-13-1 ]
[ 1101217-75-7 ]

Yield	Reaction Conditions	Operation in experiment
89%		Synthesis 27Diethyl 2-((6-chloropyridin-3-yl)methyl)-2-ethylmalonate (27)To a solution of diethyl 2-ethylmalonate (99%, 880 muIota_, 4.6 mmol, 1.2 eq) in dry DMF (10 ml_), sodium hydride (60% dispersion in mineral oil, 222 mg, 5.5 mmol, 1 .4 eq) was added at 0C. The suspension was stirred under nitrogen atmosphere at 0C for 1 hour. Then 26 (800 mg, 3.9 mmol, 1 eq) was added. The solution was stirred at room temperature under nitrogen atmosphere for 4.5 hours. The reaction mixture was quenched with a saturated aqueous NH4CI solution and extracted with small portions of diethyl ether. The collected organic phases were dried over anhydrous Na2S04, filtered and the solvent was removed in vacuo. The residue was purified by flashchromatography on silica gel (gradient: from n-Hex/EtOAc 9:1 to n-Hex/EtOAc 8.5:1 .5) to give 1.087 g of 27 (89%) as a pale yellow oil.Rf = 0.25 (n-Hex/EtOAc 9:1 ). 1 H NMR (400 MHz, CDCI3) delta 8.1 1 (d, J = 2.1 Hz, 1 H), 7.40 (dd, J = 8.2, 2.5 Hz, 1 H), 7.19 (d, J = 8.2 Hz, 1 H), 4.22 - 4.06 (m, 4H), 3.15 (s, 2H), 1 .82 (q, J = 7.5 Hz, 2H), 1.19 (t, J = 7.1 Hz, 6H), 0.89 (t, J = 7.5 Hz, 3H); 13C NMR (100 MHz, CDCI3) 5 170.9, 151 .1 , 150.4, 140.4, 131 .4, 124.0, 61.7, 59.4, 34.6, 25.8, 14.3, 8.8; ESI MS m/z: calcd. for Ci5H2iCIN04 [/W+H]+ 314.1 , Ci5H20CINNaO4 [/W+Na]+ 336.1 , found: 314.1 , 316.1 , 336.1 , 338.1 .

Reference： [1]Patent: WO2013/38153,2013,A1 .Location in patent: Page/Page column 94

22
[ 182924-36-3 ]
[ 1427731-16-5 ]

Reference： [1]Patent: WO2013/38153,2013,A1

23
[ 22536-61-4 ]
[ 182924-36-3 ]

Yield	Reaction Conditions	Operation in experiment
38%	With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 6h;Reflux;	Synthesis Example 25 N-[1-((2-chloropyrimidin-5-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide (Compound 243) 2-chloro-5-methylpyrimidine (1.04 g, 8.13 mmol) was dissolved in 30 mL of carbon tetrachloride, 1.73 g (9.75 mmol) of N-bromosuccinimide and 20 mg of benzoyl peroxide were added, and the mixture was refluxed under heating for 6 hours. Following reaction completion, the reaction mixture was returned to room temperature, concentrated under reduced pressure, and purified by silica gel column chromatography (hexane/ethyl acetate=3:1), affording 641 mg of 5-bromomethyl-2-chloropyridine (yield, 38%). 1H-NMR (CDCl3, delta, ppm): 4.42 (2H, s), 8.66 (2H, s)

Reference： [1]Patent: US2013/150414,2013,A1 .Location in patent: Paragraph 0437

24
[ 182924-36-3 ]
[ 457-50-1 ]
[ 1363400-89-8 ]

Yield	Reaction Conditions	Operation in experiment
58%	With potassium carbonate; In acetonitrile; for 1h;Reflux;	An amount of 104 mg (0.50 mmol) of <strong>[182924-36-3]5-bromomethyl-2-chloropyridine</strong> obtained by the above method was dissolved in 6 mL of anhydrous acetonitrile, after which 96 mg (0.50 mmol) of 2,2,2-trifluoro-N-(pyridin-2(1H)-ylidene)acetamide obtained by the method in "Synthesis Example 14, Step (1)" and 76 mg (0.55 mmol) of potassium carbonate were added, and the mixture was refluxed under heating for 1 hour. Following reaction completion, the reaction mixture was returned to room temperature, the insoluble matter was removed by filtration, and the filtrate was concentrated under reduced pressure. Diethyl ether was added to the concentrate, whereupon a solid separated out. The solid was collected by filtration, washed with diethyl ether, then placed in a desiccator and dried under reduced pressure, affording the target compound in an amount of 92 mg (yield, 58%). 1H-NMR (CDCl3, delta, ppm): 5.54 (2H, s), 6.98 (1H, m), 7.87 (1H, m), 8.18 (1H, m), 8.48 (1H, m), 8.83 (2H, m) 13C-NMR (CDCl3, delta, ppm): 60.0, 115.6, 117.1 (q), 122.1, 127.5, 139.2, 142.9, 158.8, 160.3 (2C), 161.4, 163.8 (q) MS: m/z=317 (M+H)

Reference： [1]Patent: US2013/150414,2013,A1 .Location in patent: Paragraph 0439; 0440; 0441; 0442

25
[ 109-12-6 ]
[ 182924-36-3 ]
[ 98-88-4 ]
[ 1461716-44-8 ]

Yield	Reaction Conditions	Operation in experiment
90%		A solution of 2-chloro(5-methylboromo)pyridine (12.80 g, 62 mmol) and 2-aminopyrimidine (5.930 g, 62 mmol) in DMF (100 ml), was heated to 80 C for 18 hours. The reaction was then concentratedin vacuo, and THF (150 ml) was added to the residue. The slurry was stirred for 24 hoursat room temperature and a precipitate formed. The solid was then filtered through a frit, washed with THF, dried in a vacuum oven at 40C for 18 hours and carried on without further purification.To a portion of the above synthesized salt (0.500 g, 1.13 mmol) in dichloromethane (1 0 ml)5 was sequentially added DMAP (0.030 g, 0.23 mmol), triethylamine (0.340 mg, 3.38 mmol), andbenzoyl chloride (0.240 g, 1.69 mmol). The reaction was then stirred at room temperature for 18hours. The reaction was then diluted with ethyl acetate (150 ml), and washed with water (1 00ml) dried over Na2S04 and concentrated in vacuo to afford a residue. The residue was purifiedby flash chromatography over silica gel (MeOH/CH2CI2-gradient) to afford the product E-1 as an10 orange wax (0.400 g, 90%).LC-MS: [M+H]+ 325.3; tR = 0.85 min

Reference： [1]Patent: WO2013/144223,2013,A1 .Location in patent: Page/Page column 85; 86

26
[ 182924-36-3 ]
1,3-dimethyl-8-(3-(trifluoromethyl)phenoxy)-1H-purine-2,6(3H,7H)-dione [ No CAS ]
7-((6-chloropyridin-3-yl)methyl)-1,3-dimethyl-8-(3-(trifluoromethyl)phenoxy)-1H-purine-2,6(3H,7H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
14.6%	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃;	To a solution of 1,3-dimethyl-8-(3-(trifluoromethyl)phenoxy)-1H-purine-2,6(3H,7H)-dione (100 mg, 0.294 mmol, Intermediate 5) in DMF (3 mL) was added <strong>[182924-36-3]5-(bromomethyl)-2-chloropyridine</strong> (137 mg, 0.668 mmol) followed by potassium carbonate (122 mg, 0.883 mmol). The mixture was stirred at 80 C. overnight. The mixture was diluted with ethyl acetate and water, and the phases were separated. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated to give crude product. This material was purified by silica gel chromatography eluting with DCM/methanol=100:1 and washed with ethanol and dried in vacuo to give 7-((6-chloropyridin-3-yl)methyl)-1,3-dimethyl-8-(3-(trifluoromethyl)phenoxy)-1H-purine-2,6(3H,7H)-dione (20 mg, 14.6%) as white solid. 1H-NMR (DMSO-d6) delta 8.52-8.51 (d, 1H), 7.92-7.86 (m, 2H), 7.76-7.71 (m, 3H), 7.55-7.53 (d, 1H,) 3.24 (s, 3H), 3.29 (s, 3H). LCMS retention time 2.645 min; LCMS MH+ 466. The following examples 34a to 34p were prepared using the general method of Example 33.

Reference： [1]Patent: US2014/275528,2014,A1 .Location in patent: Paragraph 0539; 0540

27
[ 182924-36-3 ]
7-({3-[(tert-butyldimethylsilyl)oxy]propyl}thio)-4-isobutyl-2-methyl-2,6-dihydro-1H-pyrrolo[3,4-d]pyridazin-1-one [ No CAS ]
6-[(6-chloropyridin-3-yl)methyl]-7-[(3-hydroxypropyl)thio]-4-isobutyl-2-methyl-2,6-dihydro-1H-pyrrolo[3,4-d]pyridazin-1-one [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2015,vol. 2015,p. 1764 - 1770

28
[ 182924-36-3 ]
7-({3-[(tert-butyldimethylsilyl)oxy]propyl}thio)-4-isobutyl-2-methyl-2,6-dihydro-1H-pyrrolo[3,4-d]pyridazin-1-one [ No CAS ]
C₂₆H₃₉ClN₄O₂SSi [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2015,vol. 2015,p. 1764 - 1770
[2]MedChemComm,2016,vol. 7,p. 900 - 905

29
[ 182924-36-3 ]
6-bromo-7-methoxyquinolin-2(1H)-one [ No CAS ]
6-bromo-1-((6-chloropyridin-3-yl)methyl)-7-methoxyquinolin-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
17%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 16h;	To a solution of intermediate-5 (0.2 g, 0.78 mmol) in DMF (5 mL) were add potassium carbonate (0.32 g, 0.99 mmol) followed by 2-chloro-5-(chloromethyl)pyridine (0.33 g, 2.36 mmol) and stirred at RT for 16 h. After completion of the reaction, the reaction mixture was diluted with water and extracted with EtOAc (200 mL X 2). The combined organic layers werewashed with water (200 mL), brine (100 mL), dried over sodium sulphate and concentrated. The residue was purified by preparative TLC to afford the title product as an off white solid (0.05 g, 17%). 1H NMR (400 MHz, DMSO-d6): oe 8.44 (d, J=2.5 Hz, 1H), 8.04 (s, 1H), 7.90 (d, J=9.3 Hz, 1H), 7.67 (dd, J=5.9 & 2.4 Hz, 1H), 7.46 (d, J=8.3 Hz, 1H), 6.98 (s, 1H), 6.60 (d, J=9.3 Hz, 1H),5.60 (s, 2H), 3.86 (s, 3H); LC-MS: mlz 379.0 (M+1).

Reference： [1]Patent: WO2015/104653,2015,A1 .Location in patent: Page/Page column 42; 43

30
[ 182924-36-3 ]
tert-butyl 2-(4-hydroxy-2-oxo-1,2,5,7-tetrahydrofuro[3,4-b]pyridine-3-carboxamido)acetate [ No CAS ]
tert-butyl 2-(1-((6-chloropyridin-3-yl)methyl)-4-hydroxy-2-oxo-1,2,5,7-tetrahydrofuro[3 ,4-b]pyridine-3-carboxamido)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetone; at 25 - 50℃; for 16h;Inert atmosphere;	To a solution of Intermediate 2 (200 mg, 0.64 mmol) and 5-(bromomethyl)-2- chloropyridine (159 mg, 0.77 mmol) in acetone (4.0 mL) and DMF (2.0 mL) was added K2C03 (134 mg, 0.96 mmol) at 25 C. Then the reaction mixture was stirred at 50C under N2 for 16 hours. When TLC showed the reaction was completed, the reaction mixture was partitioned between water (100 mL) and EtOAc (100 mL), and the aq. phase was extracted with EtOAc(100 mL x 2). The combined organic layers were washed with brine (50 mL), dried overNa2504 and concentrated under vacuum. The residue was purified by prep. TLC (eluted withPE/EtOAc = 2:1) to afford tert-butyl 2-(1-((6-chloropyridin-3-yl)methyl)-4-hydroxy-2-oxo-1 ,2,5,7-tetrahydrofuro[3 ,4-b] pyridine-3 -carboxamido)acetate. ?H NMR (400 MHz, CDC13) oe16.04 (s, 1H), 10.36 (t, J= 5.6 Hz, 1H), 8.32 (s, 1H), 7.65-7.63 (m, 1H), 7.33-7.31 (m, 1H),5.065.05 (m, 2H), 5.014.99 (m, 4H), 4.09 (d, J= 5.6 Hz, 2H), 1.50 (s, 9H). LC/MS (m/z): 436 (M+H).

Reference： [1]Patent: WO2016/49100,2016,A1 .Location in patent: Page/Page column 44

31
[ 182924-36-3 ]
(E)-1-(5-((6-chloropyridin-3-yl)methoxy)-2-hydroxyphenyl)-3-(dimethylamino)prop-2-en-1-one [ No CAS ]

Reference： [1]Patent: WO2016/97345,2016,A1

32
[ 182924-36-3 ]
6-((6-chloropyridin-3-yl)methoxy)-4H-chromen-4-one [ No CAS ]

Reference： [1]Patent: WO2016/97345,2016,A1

33
[ 182924-36-3 ]
[ 490-78-8 ]
1-(5-((6-chloropyridin-3-yl)methoxy)-2-hydroxyphenyl)ethan-1-one [ No CAS ]