[ CAS No. 862129-81-5 ] {[proInfo.proName]}

Name: 862129-81-5|2-(3,6-Dihydro-2H-thiopyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|97%
Brand: Ambeed
SKU: A102956
Price: 15.0 USD
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Quality Control of [ 862129-81-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 862129-81-5 ]

SDS Specification

Alternatived Products of [ 862129-81-5 ]

Product Details of [ 862129-81-5 ]

CAS No. :	862129-81-5	MDL No. :	MFCD10700154
Formula :	C₁₁H₁₉BO₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QZVRTORVCKGPPY-UHFFFAOYSA-N
M.W :	226.14	Pubchem ID :	46739735
Synonyms :

Calculated chemistry of [ 862129-81-5 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.82
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	66.94
TPSA :	43.76 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.19 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	2.1
Log Po/w (WLOGP) :	2.68
Log Po/w (MLOGP) :	1.67
Log Po/w (SILICOS-IT) :	1.89
Consensus Log Po/w :	1.67

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.5
Solubility :	0.717 mg/ml ; 0.00317 mol/l
Class :	Soluble
Log S (Ali) :	-2.65
Solubility :	0.507 mg/ml ; 0.00224 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.74
Solubility :	0.415 mg/ml ; 0.00184 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.74

Safety of [ 862129-81-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 862129-81-5 ]

* 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 [ 862129-81-5 ]
Downstream synthetic route of [ 862129-81-5 ]

[ 862129-81-5 ] Synthesis Path-Upstream 1~5

1
[ 181180-42-7 ]
[ 73183-34-3 ]
[ 862129-81-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium acetate In dimethyl sulfoxide at 70℃; for 12 h;	Combine diisopropylamine (2.5 mL, 18.1 mmol) and tetrahydrofuran (25 mL) and cool to 0°C. Add n-butyllithium (11 mL, 18.1 mmol, 1.6 M in hexanes) dropwise over 15 minutes. Cool to-78°C. Add tetrahydro-thiopyran-4-one (2 g, 17.2 mmol) dropwise over 20 minutes as a solution in tetrahydrofuran (20 mL). Stir at-78°C for 20 minutes. Add N-phenylbis (trifluoromethanesulfonimide) (6.8 g, 18.9 mmol) from a powder addition funnel and rinse into the reaction with tetrahydrofuran (5 mL). Allow to warm to ambient temperature and stir overnight. Partition between ether (100 mL) and 1 M aqueous sodium hydroxide (25 mL). Separate organic and wash with 1 M aqueous sodium bisulfate (25 mL) and finally with saturated aqueous brine. Dry the organic over sodium sulfate, decant, and concentrate in vacuo. Purify the residue by column chromatography using a silica gel column eluting with a linear gradient beginning with hexanes and ending with 5: 1 hexanes : ethyl acetate. Isolate 3.5 g (81percent) of trifluoro-methanesulfonic acid 3,6- dihydro-2H-thiopyran-4-yl ester after concentrating the fractions. Combine trifluoro-methanesulfonic acid 3,6-dihydro-2H-thiopyran-4-yl ester (1 g, 4.0 mmol), bis (pinacolotodiboron) (1.1 g, 4.4 mmol) and dimethylsulfoxide (15 mL). Bubble nitrogen through this solution for 15 minutes. Add potassium acetate (1.2 g, 12 mmol) and dichloro [1, 1'-bis (diphenylphosphino) ferrocene] palladium dichloromethane adduct (290 mg, 0.40 mmol). Heat the mixture to 70°C for 12 hours. Cool to ambient temperature. Partition between ether (100 mL) and water (25 mL). Extract the organic component. Wash the organic with saturated aqueous brine (25 mL). Dry over sodium sulfate, decant, and concentrate in vacuo. Purify the residue by column chromatography using a 5percent triethylamine/hexanes prewashed silica gel column eluting with 1: 1 ether: hexanes to give 900 mg (100percent) of 2- (3, 6-dihydro-2H-thiopyran-4-yl) -4,4, 5,5- tetramethyl- [1, 3,2] dioxaborolane after concentrating the fractions.
53%	With 1,1'-bis(diphenylphosphino)ferrocene; potassium acetate In 1,4-dioxane at 80℃; for 16 h;	A mixture of 2.0 g (8.1 mmol) trifluoro-methanesulfonic acid 3,6-dihydro-2H-thiopyran-4-yl ester, 2.3 g (8.9 mmol) bis(pinacolato)diboron, 0.18 g (0.24 mmol) dichloro(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloromethane, 0.13 g (0.24 mmol) 1,1'-bis(diphenylphosphino)ferrocene and 2.4 g (24 mmol) potassium acetate in 20 ml dioxane was stirred at 80° C. for 16 h. After cooling to room temperature the reaction mixture was diluted with water and brine (1:1) and extracted with three portions of tert-butyl methyl ether. The combined organic extracts were washed with brine, dried over sodium sulfate and concentrated in vacuo. Flash column chromatography gave 0.97 g (53percent) of the title compound as an orange resin

Reference： [1] Patent: WO2005/73206, 2005, A1, . Location in patent: Page/Page column 14-15
[2] Patent: WO2015/89327, 2015, A1, . Location in patent: Paragraph 0255
[3] Patent: US2006/30600, 2006, A1, . Location in patent: Page/Page column 18
[4] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 13, p. 3544 - 3549
[5] Patent: WO2010/57121, 2010, A1, . Location in patent: Page/Page column 195
[6] Patent: US2015/284411, 2015, A1, . Location in patent: Paragraph 0648; 0649

2
[ 76-09-5 ]
[ 121-43-7 ]
[ 862129-81-5 ]

Yield	Reaction Conditions	Operation in experiment
62%	With hydrogenchloride; magnesium; methyl iodide In tetrahydrofuran; water; ethyl acetate at 20℃; Reflux	Step two: adding metal magnesium (2.2 g, 92mmol) and 10 ml of tetrahydrofuran, add 2-3 drop iodine methane initiating the dropwise 13.8 g 3,6-dihydro -2H-pyran-4-polybromide dissolved in 60 ml tetrahydrofuran solution, reagent cheng Geshi preparing reflux reaction is omitted, then drop by adding boric acid three methyl ester (11.4 g, 0 . 11mol) in, after the reaction is complete, by adding 10percent hydrochloric acid solution to adjust PH= 3-4, organic layer by adding 110 ml of ethyl acetate and pinacone (9.4 g, 80mmol), stirring at room temperature until the reaction is complete. After laminating, an organic layer saturated salt water washing, solvent after evaporation to dryness, by adding normal heptane, cooling to -10 °C, obtained after filtering 10.8 g kind of white solid: 3,6-dihydro -2H-thiopyran-4-boronic acid pinacone ester, GC: 99.0percent, HNMR > 98percent, the yield is 62percent.

Reference： [1] Patent: CN105503927, 2016, A, . Location in patent: Paragraph 0015

3
[ 121-43-7 ]
[ 126-30-7 ]
[ 862129-81-5 ]

Yield	Reaction Conditions	Operation in experiment
64%	With hydrogenchloride; magnesium; methyl iodide In tetrahydrofuran; water; ethyl acetate at 20℃; Reflux	Step two: adding metal magnesium (2.2 g, 92mmol) and 10 ml of tetrahydrofuran, add 2-3 drop iodine methane initiating the dropwise 13.2 g 3,6-dihydro -2H-pyran-4-polybromide dissolved in 60 ml tetrahydrofuran solution, reagent cheng Geshi preparing reflux reaction is omitted, then drop by adding boric acid three methyl ester (11.4 g, 0 . 11mol) in, after the reaction is complete, by adding 10percent hydrochloric acid solution to adjust PH= 3-4, organic layer by adding 110 ml of ethyl acetate and npg (10.0 g, 96mmol), stirring at room temperature until the reaction is complete. After laminating, an organic layer saturated salt water washing, solvent after evaporation to dryness, by adding normal heptane, cooling to -10 °C, filtering to obtain 10.0 g kind of white solid: 3,6-dihydro -2H-thiopyran-4-boronic acid new pentamethylene glycol ester, GC: 99.7percent, HNMR > 98percent, the yield is 64percent.

Reference： [1] Patent: CN105503927, 2016, A, . Location in patent: Paragraph 0016

4
[ 1072-72-6 ]
[ 862129-81-5 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 13, p. 3544 - 3549
[2] Patent: WO2015/89327, 2015, A1,
[3] Patent: US2015/284411, 2015, A1,
[4] Patent: CN105503927, 2016, A,

5
[ 73183-34-3 ]
[ 862129-81-5 ]

Reference： [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 3, p. 847 - 850[2] Angew. Chem., 2017, vol. 129, p. 865 - 868,4

[ 862129-81-5 ] Synthesis Path-Downstream 1~64

1
[ 181180-42-7 ]
[ 73183-34-3 ]
[ 862129-81-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In dimethyl sulfoxide; at 70℃; for 12h;	Combine diisopropylamine (2.5 mL, 18.1 mmol) and tetrahydrofuran (25 mL) and cool to 0C. Add n-butyllithium (11 mL, 18.1 mmol, 1.6 M in hexanes) dropwise over 15 minutes. Cool to-78C. Add tetrahydro-thiopyran-4-one (2 g, 17.2 mmol) dropwise over 20 minutes as a solution in tetrahydrofuran (20 mL). Stir at-78C for 20 minutes. Add N-phenylbis (trifluoromethanesulfonimide) (6.8 g, 18.9 mmol) from a powder addition funnel and rinse into the reaction with tetrahydrofuran (5 mL). Allow to warm to ambient temperature and stir overnight. Partition between ether (100 mL) and 1 M aqueous sodium hydroxide (25 mL). Separate organic and wash with 1 M aqueous sodium bisulfate (25 mL) and finally with saturated aqueous brine. Dry the organic over sodium sulfate, decant, and concentrate in vacuo. Purify the residue by column chromatography using a silica gel column eluting with a linear gradient beginning with hexanes and ending with 5: 1 hexanes : ethyl acetate. Isolate 3.5 g (81%) of trifluoro-methanesulfonic acid 3,6- dihydro-2H-thiopyran-4-yl ester after concentrating the fractions. Combine trifluoro-methanesulfonic acid 3,6-dihydro-2H-thiopyran-4-yl ester (1 g, 4.0 mmol), bis (pinacolotodiboron) (1.1 g, 4.4 mmol) and dimethylsulfoxide (15 mL). Bubble nitrogen through this solution for 15 minutes. Add potassium acetate (1.2 g, 12 mmol) and dichloro [1, 1'-bis (diphenylphosphino) ferrocene] palladium dichloromethane adduct (290 mg, 0.40 mmol). Heat the mixture to 70C for 12 hours. Cool to ambient temperature. Partition between ether (100 mL) and water (25 mL). Extract the organic component. Wash the organic with saturated aqueous brine (25 mL). Dry over sodium sulfate, decant, and concentrate in vacuo. Purify the residue by column chromatography using a 5% triethylamine/hexanes prewashed silica gel column eluting with 1: 1 ether: hexanes to give 900 mg (100%) of 2- (3, 6-dihydro-2H-thiopyran-4-yl) -4,4, 5,5- tetramethyl- [1, 3,2] dioxaborolane after concentrating the fractions.
53%	With 1,1'-bis(diphenylphosphino)ferrocene; potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; at 80℃; for 16h;	A mixture of 2.0 g (8.1 mmol) trifluoro-methanesulfonic acid 3,6-dihydro-2H-thiopyran-4-yl ester, 2.3 g (8.9 mmol) bis(pinacolato)diboron, 0.18 g (0.24 mmol) dichloro(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloromethane, 0.13 g (0.24 mmol) 1,1'-bis(diphenylphosphino)ferrocene and 2.4 g (24 mmol) potassium acetate in 20 ml dioxane was stirred at 80 C. for 16 h. After cooling to room temperature the reaction mixture was diluted with water and brine (1:1) and extracted with three portions of tert-butyl methyl ether. The combined organic extracts were washed with brine, dried over sodium sulfate and concentrated in vacuo. Flash column chromatography gave 0.97 g (53%) of the title compound as an orange resin
	With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; water; at 100℃; for 24h;	A mixture of 3 ,6-dihydro-2H-thiopyran-4-yl trifluoromethanesulfonate (4.5 g, 18.13 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(l,3,2-dioxaborolane) (6.90 g, 27.2 mmol), potassium acetate (5.34 g, 54.4 mmol), and PdCl2(dppf)2 (1.480 g, 1.813 mmol) in p- dioxane/H2O (10:1, 22 ml) was heated at 1000C in 24h, cooled, diluted with EtOAc, washed with H2O, dried over MgSO4, concentrated and purified by ISCO (0-10% EtOAc/Hexanes) to give the yellow oil. MS [M+l]: 227.1.

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; water; at 100℃; for 20h;Inert atmosphere;

1,1?-Bis(diphenyl-phosphino)ferrocene-palladium(II)dichloride dichoromethane complex (219.0 mg, 0.268 mmol) was added to a suspension of 3,6-dihydro-2H-thiopyran-4-yl trifluoromethanesulfonate (Intermediate 42, 666.1 mg, 2.68 mmol), bis(pinacolato)diboron (1.022 g, 40.02 mmol), and potassium acetate (790.0 mg, 8.05 mmol) in degassed 10% water in dioxane (3.3 mL). The mixture was stirred at 100 C. for 20 h, then cooled to RT and added to stirring EtOAc (70 mL)/water (25 mL). The organic layer was separated and dried over Na2SO4, filtered, and evaporated under reduced pressure. Flash chromatography of the resulting residue utilizing a 40 g silica RediSep Rf Gold column and employing a 0-100% EtOAc/hexane gradient afforded the title compound. LC-MS: calculated for C11H19BO2S 226.12 observed m/e: 227.10 (M+H)+ (Rt 1.47/2.0 min)

Reference： [1]Patent: WO2005/73206,2005,A1 .Location in patent: Page/Page column 14-15
[2]Patent: WO2015/89327,2015,A1 .Location in patent: Paragraph 0255
[3]Patent: US2006/30600,2006,A1 .Location in patent: Page/Page column 18
[4]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 3544 - 3549
[5]Patent: WO2010/57121,2010,A1 .Location in patent: Page/Page column 195
[6]Patent: US2015/284411,2015,A1 .Location in patent: Paragraph 0648; 0649

2
[ 648904-46-5 ]
[ 862129-81-5 ]
[ 862129-83-7 ]

Yield	Reaction Conditions	Operation in experiment
90%	With cesium fluoride;palladium diacetate; tricyclohexylphosphine; In toluene; acetonitrile; for 4h;Heating / reflux;	Combine trifluoromethanesulfonic acid 6-methoxy-1- [4- (2-piperidin-1-yl-ethoxy)- phenoxy]-naphthalen-2-yl ester (780 mg, 1.5 mmol) and 2- (3, 6-dihydro-2H-thiopyran-4- yl) -4,4, 5, 5-tetramethyl- [1, 3,2] dioxaborolane (700 mg, 3.0 mmol) in acetonitrile (25 mL). Bubble nitrogen through the solution for 10 minutes. Add palladium (II) acetate (34 mg, 0.15 mmol), tricyclohexylphosphine (0.36 mL, 0.23 mmol, 20% solution in toluene), and cesium fluoride (2.0 g, 13.3 mmol). Fit the flask with a reflux condenser and heat to reflux for 4 hours. Cool to ambient temperature and dilute with dichloromethane (50 mL) and saturated aqueous ammonium chloride (10 mL). Separate the organic and wash the aqueous twice with dichloromethane (10 mL). Combine the organics and dry over magnesium sulfate. Filter and concentrate in vacuo. Purify the residue by column chromatography using a silica gel column eluting with a linear gradient beginning with dichloromethane and ending with 5: 1 dichloromethane: methanol to give 650 mg (90%) of 1- (2- {4- [2- (3, 6-dihydro-2H-thiopyran-4-yl)-6-methoxy-naphthalen-1-yloxy]-phenoxy}- ethyl) -piperidine after concentrating the fractions. Redissolve in methanol (10 mL) and dichloromethane (20 mL). Add water (8 mL) and oxone (2.0 g, 3.4 mmol). Stir at ambient temperature for 4 hours. Dilute with dichloromethane (50 mL) and saturated aqueous sodium bicarbonate. Separate the organic, dry over magnesium sulfate, filter and concentrate in vacuo. Purify the residue by column chromatography using a silica gel column eluting with a linear gradient beginning with dichloromethane and ending with 5: 1 dichloromethane: methanol to give 370 mg (53%) of the title compound after concentrating the fractions: mass spectrum (ion spray): m/z = 508.1 (M+H).

Reference： [1]Patent: WO2005/73206,2005,A1 .Location in patent: Page/Page column 15-16
[2]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 3544 - 3549

3
[ 1072-72-6 ]
[ 862129-81-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 3544 - 3549
[2]Patent: WO2015/89327,2015,A1
[3]Patent: US2015/284411,2015,A1
[4]Patent: CN105503927,2016,A

4
[ 862129-81-5 ]
[ 862129-82-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 3544 - 3549

5
[ 862129-81-5 ]
[ 862129-85-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 3544 - 3549

7
[ 862129-81-5 ]
[ 1227068-54-3 ]
[ 1227068-55-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;bis(tri-tert-butylphosphine)palladium(0); In 1,4-dioxane; water; at 120℃; for 4h;	A mixture of 4-(3 -chloropyrazin-2-yloxy)-N-methoxy-N-methylbenzamide ( 1.4 g, 4.77 mmol), 2-(3,6-dihydro-2H-thiopyran-4-yl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (1.132 g, 5.01 mmol), potassium carbonate (1.976 g, 14.30 mmol), and bis(tri-tert- butylphosphine)palladium(O) (0.244 g, 0.477 mmol) in p-dioxane/H2theta (10:1, 11 ml) was heated to 120^C in 4h, cooled, taken up in H2O, extracted with EtOAc (3x), dried over MgSO4, concentrated and purified by ISCO (50% EtOAc/hexanes) to give the titled compound. MS [M+l]: 358.1.

Reference： [1]Patent: WO2010/57121,2010,A1 .Location in patent: Page/Page column 196

8
[ 862129-81-5 ]
[ 857730-21-3 ]
[ 1354290-83-7 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; tricyclohexylphosphine;tris-(dibenzylideneacetone)dipalladium(0); In 1,4-dioxane; water; at 90.0℃; for 22.0h;Inert atmosphere;	4-Amino-5-bromo-2-chloropyridine (1.17 g, 5.6 mmol), 2-(3,6-dihydro-2H- thiopyran-4-yl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (1.65 g, 7.3 mmol), tricyclohexylphosphine (254 mg, 0.91 mmol), and tris(dibenzylideneacetone)- dipalladium (0) (413 mg, 0.45 mmol) were added to a flask then degassed and backfilled with argon. To the flask, 1,4-dioxane (16 mL) and aq. 1.3M potassium phosphate tribasic (13.1 mL, 17 mmol) were added by syringe. The resulting reaction was heated to 90 C and monitored with TLC and LC-MS. After 22 h, the reaction was cooled to rt then poured into water. After extracting twice with EtOAc and twice with DCM, the combined organic extractions were dried over anhydrous magnesium sulfate. After filtration and concentration, the residue was purified on silica gel (0-50% EtOAc in hexanes) to afford a brown film as 2- chloro-5-(3,6-dihydro-2H-thiopyran-4-yl)pyridin-4-amine that was used without further purification.

Reference： [1]Patent: WO2012/3283,2012,A1 .Location in patent: Page/Page column 167

9
[ 862129-81-5 ]
[ 1354288-81-5 ]

Reference： [1]Patent: WO2012/3283,2012,A1

10
[ 862129-81-5 ]
[ 1354290-85-9 ]

Reference： [1]Patent: WO2012/3283,2012,A1

11
[ 862129-81-5 ]
[ 1354288-82-6 ]

Reference： [1]Patent: WO2012/3283,2012,A1

12
[ 862129-81-5 ]
[ 1354286-50-2 ]

Reference： [1]Patent: WO2012/3283,2012,A1

13
[ 862129-81-5 ]
[ 1354290-08-6 ]
[ 1354286-15-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; tricyclohexylphosphine;tris-(dibenzylideneacetone)dipalladium(0); In 1,4-dioxane; water; at 90℃; for 19h;Inert atmosphere;	N-(5-bromo-2-morpholinopyridin-4-yl)-5,7-difluoro-3-methyl-2-(pyridin-2-yl)- quinolin-4-amine (68.2 mg, 0.13 mmol), 2-(3,6-dihydro-2H-thiopyran-4-yl)- 4,4,5, 5-tetramethyl-l,3,2-dioxaborolane (45.8 mg, 0.20 mmol), tricyclohexyl- phosphine (6.2 mg, 0.022 mmol), and tris(dibenzylideneacetone)dipalladium (0) (10.3 mg, 0.011 mmol) were added to a flask then degassed and backfilled with argon. To the flask, 1,4-dioxane (2.0 mL) and aq. 1.3M potassium phosphate tribasic (0.31 mL, 0.4 mmol) were added by syringe. The resulting reaction was heated to 90 C and monitored with TLC and LC-MS. After 19 h, the reaction was cooled to rt then poured into water. After extracting twice with EtOAc and twice with DCM, the combined organic extractions were dried over anhydrous magnesium sulfate. After filtration and concentration, the residue was purified on silica gel (0-40% of a premixed solution of 89:9: 1 DCM: MeOH: ammonium hydroxide in DCM) to afford a film that was triturated with MeOH to afford a white solid as N-(5-(3,6-dihydro-2H-thiopyran-4-yl)-2-morpholinopyridin-4-yl)- 5,7-difluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-amine. 1H NMR (500 MHz, CDC13) delta ppm 8.75 (1 H, m), 7.96 (3 H, m), 7.65 (1 H, d, J=9.0 Hz), 7.40 (1 H, ddd, J=6.5, 4.7, 2.2 Hz), 7.11 (1 H, m), 7.08 (1 H, m), 6.13 (1 H, br. s.), 5.71 (1 H, s), 3.85 (4 H, m), 3.39 (6 H, m), 2.91 (2 H, t, J=5.7 Hz), 2.63 (2 H, m), 2.26 (3 H, s). Mass Spectrum (pos.) m/e: 532.2 (M+H)+.

Reference： [1]Patent: WO2012/3283,2012,A1 .Location in patent: Page/Page column 142-143

14
[ 862129-81-5 ]
[ 1537169-11-1 ]
[ 1537169-10-0 ]

Yield	Reaction Conditions	Operation in experiment
45%	With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate; In 1,2-dimethoxyethane; water; at 90℃; for 2h;Inert atmosphere; Sealed tube;	Intermediate 6 (50 mg, 0.136 mmol), 2-(3,6-dihydro-2H-thiopyran-4-yl)-4,4,5,5- tetramethyl-l,3,2-dioxaborolane (46.07 mg, 0.2 mmol) and a 2M solution of sodium bicarbonate in water (0.43 mL) were combined in 1 ,2-dimethoxy ethane (2.2 mL) and the mixture was degassed thoroughly under nitrogen. Tetrakis(triphenylphosphine)- palladium(O) (16 mg, 0.014 mmol) was added and the mixture was heated at 90C in a sealed tube for 2 h. The reaction mixture was cooled to room temperature and diluted using dichloromethane (10 mL). The mixture was washed using an aqueous saturated solution of sodium bicarbonate (2 x 5 mL) and brine (10 mL). The organic phase was dried over sodium sulfate and concentrated in vacuo. The crude orange oil was purified by chromatography on silica (Biotage, lOg cartridge), eluting with 0 to 100%) ethyl acetate in heptane, to afford the title compound (23.5 mg, 45%) as a yellow solid. 5H (500 MHz, CDCls) 8.94 (s, 1H), 7.74-7.66 (m, 1H), 7.32-7.27 (m, 1H), 7.16 (d, J 8.1 Hz, 1H), 7.11 (t, J7.5 Hz, 1H), 6.93-6.89 (m, 1H), 6.88 (t, J4.4 Hz, 1H), 6.63 (t, J 73.6 Hz, 1H), 4.28 (s, 2H), 3.39 (dd, J 12.7, 10.5 Hz, 2H), 2.88 (t, J 5.8 Hz, 2H), 2.69-2.61 (m, 2H), 2.55 (s, 3H). Method D HPLC-MS: MH+ mlz 388, RT 3.06 minutes
45%	With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate; In 1,2-dimethoxyethane; water; at 90℃; for 2h;Inert atmosphere; Sealed tube;	Intermediate 6 (50 mg, 0.136 mmol), <strong>[862129-81-5]2-(3,6-dihydro-2H-thiopyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane</strong> (46.07 mg, 0.2 mmol) and a 2M solution of sodium bicarbonate in water (0.43 mL) were combined in 1,2-dimethoxyethane (2.2 mL) and the mixture was degassed thoroughly under nitrogen. Tetrakis(triphenylphosphine)-palladium(0) (16 mg, 0.014 mmol) was added and the mixture was heated at 90 C. in a sealed tube for 2 h. The reaction mixture was cooled to room temperature and diluted using dichloromethane (10 mL). The mixture was washed using an aqueous saturated solution of sodium bicarbonate (2×5 mL) and brine (10 mL). The organic phase was dried over sodium sulfate and concentrated in vacuo. The crude orange oil was purified by chromatography on silica (Biotage, 10 g cartridge), eluting with 0 to 100% ethyl acetate in heptane, to afford the title compound (23.5 mg, 45%) as a yellow solid. deltaH (500 MHz, CDCl3) 8.94 (s, 1H), 7.74-7.66 (m, 1H), 7.32-7.27 (m, 1H), 7.16 (d, J 8.1 Hz, 1H), 7.11 (t, J 7.5 Hz, 1H), 6.93-6.89 (m, 1H), 6.88 (t, J4.4 Hz, 1H), 6.63 (t, J 73.6 Hz, 1H), 4.28 (s, 2H), 3.39 (dd, J 12.7, 10.5 Hz, 2H), 2.88 (t, J 5.8 Hz, 2H), 2.69-2.61 (m, 2H), 2.55 (s, 3H). Method D HPLC-MS: MH+ m/z 388, RT 3.06 minutes.

Reference： [1]Patent: WO2014/9296,2014,A1 .Location in patent: Page/Page column 138; 139
[2]Patent: US2015/191482,2015,A1 .Location in patent: Paragraph 0561

15
[ 862129-81-5 ]
[ 1595284-69-7 ]
[ 1622053-20-6 ]

Yield	Reaction Conditions	Operation in experiment
33%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; tris-(o-tolyl)phosphine; In 1,4-dioxane; at 100℃; for 4h;Inert atmosphere;	To a solution of 5-bromo-2-iodo-N-methyl-6-(N-methylmethylsulfonamido) benzofuran-3-carboxamide (800 mg, 1.6 mmol), 2-(3,6-dihydro-2H-thiopyran-4-yl) -4,4,5,5- tetram ethyl-l,3,2-dioxaborolane (371 mg, 1.6 mmol) and CS2CO3 (1.07 g, 3.28 mmol) in 1,4- dioxane (20 mL) was added Pd(dppf)Cl2 (50 mg) and tri-o-tolylphosphine (50 mg) under nitrogen. The reaction mixture was heated at 100 C for 4 h, concentrated in vacuo to remove 1,4-dioxane and purified by column chromatography (PE : EA = 3 : 1) to give the compound 5- bromo-2-(3,6-dihydro-2H-thiopyran-4-yl)-N-methyl-6-(N-methylmethylsulfonamido) benzofuran-3-carboxamide (250 mg, yield: 33%). 1H- MR (CDC13, 400 MHz) delta 8.09 (s, 1H), 7.59 (s, 1H), 6.73 (s, 1H), 6.06 (brs, 1H), 3.38 (t, J = 2.0 Hz, 2H), 3.30 (s, 3H), 3.05 (s, 3H), 3.00 (d, J = 4.8 Hz, 3H), 2.87 (t, J = 5.6 Hz, 2H), 2.70-2.76 (m, 2H). MS (M+H)+: 459 / 461.

Reference： [1]Patent: WO2014/121418,2014,A1 .Location in patent: Page/Page column 64

16
[ 862129-81-5 ]
(3R,3aR,6R,6aR)-6-(5-(4-bromophenyl)-6-chloro-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-b]pyridin-2-yloxy)hexahydrofuro[3,2-b]furan-3-ol [ No CAS ]
(3R,3aR,6R,6aR)-6-[6-chloro-5-[4-(3,6-dihydro-2H-thiopyran-4-yl)phenyl]-3-(2-trimethylsilanyl-ethoxymethyl)-3H-imidazo[4,5-b]pyridin-2-yloxy]hexahydrofuro[3,2-b]furan-3-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; water; at 90℃; for 3h;Inert atmosphere;	Step 1: (3R,3aR,6R,6aR)-6-[6-Chloro-5-[4-(3,6-dihydro-2H-thiopyran-4-yl)-phenyl]-3-(2-trimethylsilanyl-ethoxymethyl)-3H-imidazo[4,5-b]pyridin-2-yloxy]-hexahydro-furo[3,2-b]furan-3-ol [0361] The title compound is prepared from (3R,3aR,6R,6aR)-6-[5-(4-bromo-phenyl)-6-chloro-3-(2-trimethylsilanyl-ethoxymethyl)-3H-imidazo[4,5-b]pyridin-2-yloxy]-hexahydro-furo[3,2-b]furan-3-ol and <strong>[862129-81-5]2-(3,6-dihydro-2H-thiopyran-4-yl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane</strong> following a procedure analogous to that described for Intermediate 2 (Step 1). LC (method 1): tR=1.26 min; Mass spectrum (ESI+): m/z=602 [M+H]+ Step 1: (3R,3aR,6R,6aR)-6-[5-(4-Bromo-phenyl)-6-chloro-3-(2-trimethylsilanyl-ethoxymethyl)-3H-imidazo[4,5-b]pyridin-2-yloxy]-hexahydro-furo[3,2-b]furan-3-ol A mixture of (3R,3aR,6R,6aR)-6-(6-chloro-5-iodo-3-(2-trimethylsilanyl-ethoxymethyl)-3H-imidazo[4,5-b]pyridin-2-yloxy)hexahydrofuro[3,2-b]furan-3-ol (300 mg), 4-bromophenylboronic acid (120 mg), Na2CO3 (2 M aqueous solution, 810 muL), and 1,4-dioxane (4 mL) is purged for 5 minutes with argon. [1,1'-Bis(diphenylphosphino)-ferrocene]-dichloropalladium(II)-CH2Cl2-complex (PdCl2(dppf)xCH2Cl2) (30 mg) is added and the mixture is stirred for 3 h at 90 C. The reaction mixture is diluted with ethylacetate and washed with water and brine, dried over MgSO4 and concentrated in vacuo. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 40:60?20:80) to give the title compound. LC (method 1): tR=1.26 min; Mass spectrum (ESI+): m/z=582 [M+H]+.
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; water; at 90℃; for 3h;Inert atmosphere;	A mixture of (3R 3aR,6R,6aR)-6-(6-chloro-5-iodo-3-(2-trimethylsilanyl-ethoxymethyl)- 3H-imidazo[4,5-b]pyridin-2-yloxy)hexahydrofuro[3,2-b]furan-3-ol (300 mg), 4- bromophenylboronic acid (120 mg), Na2C03 (2 M aqueous solution, 810 muIota_), and 1 ,4-dioxane (4 ml_) is purged for 5 minutes with argon. [1 ,1 '-Bis(diphenylphosphino)- ferrocene]-dichloropalladium(ll)-CH2Cl2-complex (PdCI2(dppf)xCH2Cl2) (30 mg) is added and the mixture is stirred for 3 h at 90 C. The reaction mixture is diluted with ethylacetate and washed with water and brine, dried over MgS04 and concentrated in vacuo. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 40:60?20:80) to give the title compound. LC (method 1 ): tR = 1.26 min; Mass spectrum (ESI+): m/z = 582 [M+H]+

Reference： [1]Patent: US2015/25065,2015,A1 .Location in patent: Paragraph 0235-0236; 0360-0361
[2]Patent: WO2015/7669,2015,A1 .Location in patent: Page/Page column 50; 90

17
[ 862129-81-5 ]
[ 1394373-61-5 ]
(3R,3aR,6R,6aR)-6-[6-chloro-5-[4-(3,6-dihydro-2H-thiopyran-4-yl)phenyl]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazo[4,5-b]pyridin-2-yloxy]hexahydrofuro[3,2-b]furan-3-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; water; at 90℃; for 3h;Inert atmosphere;	General procedure: A mixture of (3R 3aR,6R,6aR)-6-(6-chloro-5-iodo-3-(2-trimethylsilanyl-ethoxymethyl)- 3H-imidazo[4,5-b]pyridin-2-yloxy)hexahydrofuro[3,2-b]furan-3-ol (300 mg), 4- bromophenylboronic acid (120 mg), Na2C03 (2 M aqueous solution, 810 muIota_), and 1 ,4-dioxane (4 ml_) is purged for 5 minutes with argon. [1 ,1 '-Bis(diphenylphosphino)- ferrocene]-dichloropalladium(ll)-CH2Cl2-complex (PdCI2(dppf)xCH2Cl2) (30 mg) is added and the mixture is stirred for 3 h at 90 C. The reaction mixture is diluted with ethylacetate and washed with water and brine, dried over MgS04 and concentrated in vacuo. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 40:60?20:80) to give the title compound. LC (method 1 ): tR = 1.26 min; Mass spectrum (ESI+): m/z = 582 [M+H]+

Reference： [1]Patent: WO2015/7669,2015,A1 .Location in patent: Page/Page column 50; 106; 107

18
[ 862129-81-5 ]
[ 1394373-61-5 ]
(3R,3aR,6R,6aR)-6-[6-chloro-5-[4-(tetrahydrothiopyran-4-yl)phenyl]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazo[4,5-b]pyridin-2-yloxy]hexahydrofuro[3,2-b]furan-3-ol [ No CAS ]

Reference： [1]Patent: WO2015/7669,2015,A1

19
[ 862129-81-5 ]
2-(tert-butyl)-N-(4-(6-(3,6-dihydro-2H-thiopyran-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-2-methylbenzyl)thiazole-5-carboxamide [ No CAS ]

Reference： [1]Patent: WO2015/89327,2015,A1

20
[ 862129-81-5 ]
2-(tert-butyl)-N-(4-(6-(1,1-dioxido-3,6-dihydro-2H-thiopyran-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-2-methylbenzyl)thiazole-5-carboxamide [ No CAS ]

Reference： [1]Patent: WO2015/89327,2015,A1

21
[ 862129-81-5 ]
[ 784150-41-0 ]
[ 1418128-44-5 ]

Yield	Reaction Conditions	Operation in experiment
33%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In 1,4-dioxane; water; at 90℃; for 16h;Inert atmosphere;	To a solution of aryl bromide (233 mg, 1.0 mmol) in 1,4- dioxane (8 mL) and H2O (2 mL) was added tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 2-yl)-5,6-dihyropyridine-1(2H)-carboxylate (Eunkyung, K. et al Bioorganic & Medicinal Chemistry Letters 2008, 18, 4993-4996) (245 mg, 0.8 mmol), Pd(dppf)Cl2.DCM (41 mg, 0.05 mmol) and K2CO3(276 mg, 2.0 mmol) under N2. The mixture was stirred at 110 C for 4 h, cooled to rt, diluted with H2O (80 mL) and extracted with EtOAc (60 mL x 3 . The organic layers separated, dried (Na2SO4) concentrated in vacuo to afford a residue which was purified by column chromatography (petroleum ether/EtOAc = 5:1 to 2:1) to give the title compound (77 mg, yield 23%) as yellow solid ESI-MS (M+H)+: 335.2.1H NMR (400 MHz, CDCl3) : 10.82 (br, 1H), 8.71 (s, 1H), 6.73 (s, 1H), 6.68-6.56 (m, 1H), 4.16-4.13 (m, 2H), 3.70-3.65 (m, 2H), 2.62-2.60 (m, 2H), 1.46 (s, 9H).

Reference： [1]Patent: WO2015/89327,2015,A1 .Location in patent: Paragraph 0246; 0256

22
[ 862129-81-5 ]
(3R,3aR,6R,6aR)-6-[6-chloro-5-iodo-1-(2-trimethylsilylethoxymethyl)imidazol[4,5-b]pyridin-2-yl]oxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-ol [ No CAS ]
(3R,3aR,6R,6aR)-6-((6-chloro-5-(3,6-dihydro-2H-thiopyran-4-yl)-1H-imidazo[4,5-b]pyridin-2-yl)oxy)hexahydrofuro[3,2-b]furan-3-ol [ No CAS ]

Reference： [1]Patent: US2015/284411,2015,A1

23
[ 862129-81-5 ]
(3R,3aR,6R,6aR)-6-[6-chloro-5-iodo-1-(2-trimethylsilylethoxymethyl)imidazol[4,5-b]pyridin-2-yl]oxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-ol [ No CAS ]
(3R,3aR,6R,6aR)-6-((6-chloro-5-(3,6-dihydro-2H-thiopyran-4-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazo[4,5-b]pyridin-2-yl)oxy)hexahydrofuro[3,2-b]furan-3-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 85℃; for 10h;Inert atmosphere;	Palladium tetrakistriphenylphosphine (41.7 mg, 0.036 mmol) was added to a stirred suspension of (3R,3aR,6R,6aR)-6-((6-chloro-5-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazo[4,5-b]pyridin-2-yl)oxy)-hexahydrofuro[3,2-b]furan-3-ol (Intermediate 3, 100.0 mg, 0.181 mmol), <strong>[862129-81-5]2-(3,6-dihydro-2H-thiopyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane</strong> (Intermediate 45, 61.2 mg, 0.270 mmol), and potassium phosphate tribasic (115.0 mg, 0.542 mmol) in degassed 20% water in dioxane (1.85 mL). The reaction mixture placed under N2 and heated at 85 C. for 10 h. The reaction mixture was cooled to room temperature. The lower aqueous layer drawn off and discarded. The remaining reaction mixture was evaporated under reduced pressure. Flash chromatography of the resulting residue utilizing a 12 g silica RediSep Rf Gold column and employing a 0-100% EtOAc/hexane gradient afforded the title compound. LC-MS: calculated for C23H32ClN3O5SSi 525.15 observed m/e: 526.17 (M+H)+ (Rt 1.64/2.0 min)

Reference： [1]Patent: US2015/284411,2015,A1 .Location in patent: Paragraph 0820

24
[ 1072-97-5 ]
[ 862129-81-5 ]
5-(3,6-dihydro-2H-thiopyran-4-yl)pyridin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,2-dimethoxyethane; at 115℃; for 5h;Inert atmosphere;	Step 1. 5-(3,6-Dihydro-2H-thiopyran-4-yl)pyridin-2-amine To a solution of 5-bromopyridin-2-amine (344 mg, 1.99 mmol) in DME (6 mL) was added <strong>[862129-81-5]2-(3,6-dihydro-2H-thiopyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane</strong> (300 mg, 1.33 mmol), and sodium carbonate (1.99 mL, 3.98 mmol). The mixture was purged with nitrogen for 5 min, and followed by the addition of PdCl2(dppf)-CH2Cl2 (108 mg, 0.13 mmol). The resulting mixture was heated to 115 C. in an oil bath for 5 h. The reaction mixture was diluted with ethyl acetate, washed with water, brine, dried and was concentrated. The residue was purified by flash column chromatography on silica gel (ISCO) eluting with 0-90% ethyl acetate in heptane to give Fractions were combined and concentrated to give 5-(3,6-dihydro-2H-thiopyran-4-yl)pyridin-2-amine (120 mg, 47%) as brown color solid. LCMS (m/z): 193 (MH+), 0.44 min.

Reference： [1]Patent: US9242996,2016,B2 .Location in patent: Page/Page column 65; 66; 67

25
[ 862129-81-5 ]
5-(tetrahydro-2H-thiopyran-4-yl)pyridin-2-amine [ No CAS ]

Reference： [1]Patent: US9242996,2016,B2

26
[ 862129-81-5 ]
4-(6-aminopyridin-3-yl)tetrahydro-2H-thiopyran-1,1-dioxide [ No CAS ]

Reference： [1]Patent: US9242996,2016,B2

27
[ 862129-81-5 ]
4-(6-amino-5-bromopyridin-3-yl)tetrahydro-2H-thiopyran-1,1-dioxide [ No CAS ]

Reference： [1]Patent: US9242996,2016,B2

28
[ 862129-81-5 ]
4-(6-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)tetrahydro-2H-thiopyran-1,1-dioxide [ No CAS ]

Reference： [1]Patent: US9242996,2016,B2

29
[ 862129-81-5 ]
2-[(3R)-3-methylmorpholin-4-yl]-8-[1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl]-1,7-naphthyridin-4-yl trifluoromethanesulfonate [ No CAS ]
4-(3,6-dihydro-2H-thiopyran-4-yl)-2-[(3R)-3-methylmorpholin-4-yl]-8-(1H-pyrazol-5-yl)-1,7-naphthyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In 1,2-dimethoxyethane; water; at 130℃; for 0.166667h;Microwave irradiation;	I nte rmed iate-10 (0.30 g, 0.53 mmol), 2-(3,6-d ihyd ro-2H-th iopyran-4-yl )-4,4,5,5-tetramethyl-1,3,2- dioxaborolane (0.25 g, 1.1 mmol), aq. potassium carbonate (0.85 ml, 2 M) and PdCI2(PPh3)2 (40 mg, 0.056 mmol) were solubilised in dimethoxyethane (12 ml). The reaction mixture was stirredfor 10 minutes at 130C under microwave irradiation. After cooling to rt, the reaction mixture was dried by filtration and the filtrate was concentrated under reduced pressure. The crude material was purified by preparative HPLC (acetonitrile/water/formic acid mixture). The combined fractions were concentrated under reduced pressure, solubilised in dichloromethane and washed with a saturated solution of sodium hydrogen carbonate. The organic phase was dried (siliconfilter) and concentrated under reduced pressure. The title compound was obtained in 45% yield (100 mg).?H-NMR (400MHz, DMSO-d5): 6 [ppm]= 1.27 (d, 3H), 2.56 - 2.62 (m, 2H), 2.93 (t, 2H), 3.26 - 3.32 (m, 1H), 3.36 - 3.40 (m, 2H), 3.55 (td, 1H), 3.70 (dd, 1H), 3.81 (d, 1H), 4.00 - 4.08 (m, 1H), 4.18 (d, 1H), 4.57 - 4.64 (m, 1H), 6.00 - 6.04 (m, 1H), 7.30 (s, 1H), 7.38 (br. s., 1H), 7.58 (d, 1H), 7.62 (br. s.,1H), 8.34 (d, 1H), 13.38 (br. s., 1H).

Reference： [1]Patent: WO2016/20320,2016,A1 .Location in patent: Page/Page column 256; 257

30
[ 862129-81-5 ]
tert-butyl 4-(2-amino-5-bromopyridin-3-yl)-2-fluorobenzoate [ No CAS ]
tert-butyl 4-(2-amino-5-(3,6-dihydro-2H-thiopyran-4-yl)pyridin-3-yl)-2-fluorobenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In water; butan-1-ol; at 130℃; for 0.25h;Inert atmosphere; Microwave irradiation;	Step 3. tert-butyl 4-(2-amino-5-(3,6-dihydro-2H-thiopyran-4-yl)pyridin-3-yl)-2-fluorobenzoate A degassed mixture of tert-butyl 4-(2-amino-5-bromopyridin-3-yl)-2-fluorobenzoate (400 mg, 1.09 mmol), <strong>[862129-81-5]2-(3,6-dihydro-2H-thiopyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane</strong> (296 mg, 1.31 mmol), Pd(PPh3)4 (126 mg, 0.109 mmol) in 2.0 M Na2CO3 aqueous solution (1.63 mL) and n-butanol (5 mL) was microwave heated to 130 C. for 15 min. The reaction was diluted with ethyl acetate (20 mL), and then washed with water (10 mL) and brine (10 mL). The organics were dried over sodium sulfate, filtered, concentrated, and then purified by flash chromatography (10-60% ethyl acetate/heptane eluent) to provide tert-butyl 4-(2-amino-5-(3,6-dihydro-2H-thiopyran-4-yl)pyridin-3-yl)-2-fluorobenzoate (400 mg, 95% yield). LCMS (m/z): 387.1 (MH+), 0.87 min; 1H NMR (400 MHz, CD3OD) delta ppm 7.83-7.76 (m, 2H), 7.68 (d, J=1.96 Hz, 1H), 7.37-7.34 (m, 1H), 7.33-7.29 (m, 2H), 7.28-7.24 (m, 2H), 7.24-7.18 (m, 1H), 5.10 (t, J=5.87 Hz, 1H), 3.83-3.69 (m, 2H), 2.81-2.70 (m, 2H), 2.63-2.49 (m, 3H), 2.08 (dd, J=2.74, 13.30 Hz, 2H), 1.72 (dq, J=2.93, 12.59 Hz, 2H).

Reference： [1]Patent: US9242996,2016,B2 .Location in patent: Page/Page column 375; 377

31
[ 862129-81-5 ]
1-(5-bromo-2-methoxypyridin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutane-2-ol [ No CAS ]
(1R,2S)-1-(5-(3,6-dihydro-2H-thiopyran-4-yl)-2-methoxypyridin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol [ No CAS ]
(1S,2R)-1-(5-(3,6-dihydro-2H-thiopyran-4-yl)-2-methoxypyridin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol [ No CAS ]
(1R,2R)-1-(5-(3,6-dihydro-2H-thiopyran-4-yl)-2-methoxypyridin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol [ No CAS ]
(1S,2S)-1-(5-(3,6-dihydro-2H-thiopyran-4-yl)-2-methoxypyridin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.09%; 1.08%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; water; at 60℃; for 5h;Inert atmosphere;	Under nitrogen, whichever Intermediate A (1.00g, 1.98mmol), (2- cyanophenyl) boronic acid (349mg, 2.37mmol), potassium acetate (388mg, 3.96mmol) and Pd (dppf) Cl2(92mg, 0.1mmol) was added to a dioxane / water (10mL / 2mL) mixed solvent, and the reaction was heated to 80 .LCMS and stirred for 5 hours at this temperature the reaction was monitored nitrogen protection was complete. The reaction mixture was added to water (30mL .) at the same time (10mL × 3) and extracted with ethyl acetate and the combined organic phase was dried and concentrated to give the crude compound by preparative HPLC (GX-G;. Phenomenex Synergi C18 150 * 30mm * 4um; acetonitrile 15% -45% ; water (0.225% formic acid); 25mL / min) was isolated component A and component B. Component A by chiral SFC (Berger MultiGramTM SFC, Mettler Toledo Co, Ltd, IC-10um; supercritical CO2/ MeOH (0.05% aqueous ammonia) = 60/40; 70ml / min; 220nm) was isolated compound 147 (A1) (42.14mg, 4.14% yield) and compound 148 (A2) (30.89mg, 2.96% yield) as a white The solid component B by chiral SFC (Berger MultiGramTM SFC, Mettler Toledo Co, Ltd, IC-10um; supercritical CO2/MeOH(0.05% aqueous ammonia). = 60/40; 70ml / min; 220nm) Compound 149 was isolated (B1) (40.09mg, 3.84% yield) and compound 150 (B2) (42.51mg, 4.07% yield) as a white solid.

Reference： [1]Patent: TW2016/4185,2016,A .Location in patent: Paragraph 0129; 0256; 0257

32
[ 76-09-5 ]
[ 121-43-7 ]
3,6-dihydro-2H-thiopyran-4-bromide [ No CAS ]
[ 862129-81-5 ]

Yield	Reaction Conditions	Operation in experiment
62%	With hydrogenchloride; magnesium; methyl iodide; In tetrahydrofuran; water; ethyl acetate; at 20℃;pH 3-4;Reflux;	Step two: adding metal magnesium (2.2 g, 92mmol) and 10 ml of tetrahydrofuran, add 2-3 drop iodine methane initiating the dropwise 13.8 g 3,6-dihydro -2H-pyran-4-polybromide dissolved in 60 ml tetrahydrofuran solution, reagent cheng Geshi preparing reflux reaction is omitted, then drop by adding boric acid three methyl ester (11.4 g, 0 . 11mol) in, after the reaction is complete, by adding 10% hydrochloric acid solution to adjust PH= 3-4, organic layer by adding 110 ml of ethyl acetate and pinacone (9.4 g, 80mmol), stirring at room temperature until the reaction is complete. After laminating, an organic layer saturated salt water washing, solvent after evaporation to dryness, by adding normal heptane, cooling to -10 C, obtained after filtering 10.8 g kind of white solid: 3,6-dihydro -2H-thiopyran-4-boronic acid pinacone ester, GC: 99.0%, HNMR > 98%, the yield is 62%.

Reference： [1]Patent: CN105503927,2016,A .Location in patent: Paragraph 0015

33
[ 121-43-7 ]
3,6-dihydro-2H-thiopyran-4-bromide [ No CAS ]
[ 126-30-7 ]
[ 862129-81-5 ]

Yield	Reaction Conditions	Operation in experiment
64%	With hydrogenchloride; magnesium; methyl iodide; In tetrahydrofuran; water; ethyl acetate; at 20℃;pH 3-4;Reflux;	Step two: adding metal magnesium (2.2 g, 92mmol) and 10 ml of tetrahydrofuran, add 2-3 drop iodine methane initiating the dropwise 13.2 g 3,6-dihydro -2H-pyran-4-polybromide dissolved in 60 ml tetrahydrofuran solution, reagent cheng Geshi preparing reflux reaction is omitted, then drop by adding boric acid three methyl ester (11.4 g, 0 . 11mol) in, after the reaction is complete, by adding 10% hydrochloric acid solution to adjust PH= 3-4, organic layer by adding 110 ml of ethyl acetate and npg (10.0 g, 96mmol), stirring at room temperature until the reaction is complete. After laminating, an organic layer saturated salt water washing, solvent after evaporation to dryness, by adding normal heptane, cooling to -10 C, filtering to obtain 10.0 g kind of white solid: 3,6-dihydro -2H-thiopyran-4-boronic acid new pentamethylene glycol ester, GC: 99.7%, HNMR > 98%, the yield is 64%.

Reference： [1]Patent: CN105503927,2016,A .Location in patent: Paragraph 0016

34
[ 862129-81-5 ]
2-(benzyloxy)buta-2,3-dien-1-yl benzoate [ No CAS ]
4-(3-(benzyloxy)buta-1,3-dien-2-yl)-3,6-dihydro-2H-thiopyran [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 847 - 850
Angew. Chem.,2017,vol. 129,p. 865 - 868,4

35
C₆H₇F₃O₂S₂ [ No CAS ]
[ 73183-34-3 ]
[ 862129-81-5 ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 847 - 850
Angew. Chem.,2017,vol. 129,p. 865 - 868,4

36
[ 862129-81-5 ]
1-(5-{5-[4-(²H₃)methyl-1-methyl-1H-1,2,3-triazol-5-yl]-8-[(S)-oxan-4-yl(phenyl)methyl]-3,8,10-triazatricyclo[7.4.0.02,7]trideca-1⁽⁹⁾,2⁽⁷⁾,3,5,10,12-hexaen-11-yl}thiophen-2-yl)ethan-1-one [ No CAS ]
11-(3,6-dihydro-2H-thiopyran-4-yl)-5-[4-(²H₃)methyl-1-methyl-1H-1,2,3-triazol-5-yl]-8-[(S)-oxan-4-yl(phenyl)methyl]-3,8,10-triazatricyclo[7.4.0.02,7]trideca-1⁽⁹⁾,2⁽⁷⁾,3,5,10,12-hexaene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); triethylamine; at 85℃; for 4h;Inert atmosphere;	l l-Chloro-5-[4-(2H3)methyl-l-methyl-lH-l,2,3-triazol-5-yl]-8-[(S)-oxan-4- yl(phenyl)methyl]-3,8,10-triazatricyclo[7.4.0.02,7]trideca-l(9),2(7),3,5,10,12-hexaene (200 mg, 0.420 mmol) was weighed into a 50 mL round bottom flask, followed by the addition of 2-(3,6-dihydro-2H-thiopyran-4-yl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (114 mg, 0.504 mmol), PdCl2(dppf)2.DCM (34.4 mg, 0.042 mmol), bis(di-tert-butyl(4- dimethylaminophenyl)phosphine)dichloropalladium(II) (8.9 mg, 0.013 mmol), and triethylamine (0.585 mL, 4.20 mmol). The air was replaced with N2, and the resulting mixture heated to 85C with stirring, for 4 h. It was cooled to room temperature, diluted with EtOAc, washed with brine, dried over MgS04, and concentrated to obtain a crude mixture. This was subjected to a 40 g silica gel column chromatography on a Biotage eluting with 0-10% (10% 2M NH3 in MeOH/ EtOAc)/ EtOAc to obtain 227 mg (71%) of the title compound. NMR (500MHz, DMSO-c e) delta 8.64 - 8.48 (m, 3H), 7.78 (d, J=7.3 Hz, 2H), 7.31 (t, J=7.3 Hz, 2H), 7.26 - 7.15 (m, 2H), 5.86 (br. s., 1H), 4.03 (s, 3H), 3.89 (d, J=8.8 Hz, 1H), 3.76 (d, J=9.9 Hz, 2H), 3.35 - 3.49 (m, 4H), 3.25 (t, J=11.0 Hz, 1H), 2.99 (d, J=5.5 Hz, 3H), 1.50 (br. s., 2H), 1.41 (d, J=10.3 Hz, 1H), 1.28 - 1.18 (m, 2H). LC/MS (M+H) = 540.3 [Column: Waters Aquity BEH CI 8 2.1 X 50 mm 1.7u; Mobile Phase A: water with 0.05% TFA; Mobile Phase B: ACN with 0.05% TFA; Temperature: 40 C; Gradient: 2-98% B over 1.5 min; Flow: 0.8 mL/min].

Reference： [1]Patent: WO2016/183118,2016,A1 .Location in patent: Page/Page column 300; 301

37
[ 862129-81-5 ]
1-bromo-5-cyclopropyloxy-2-methyl-4-nitrobenzene [ No CAS ]
4-(5-cyclopropoxy-2-methyl-4-nitrophenyl)-3,6-dihydro-2H-thiopyran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 100℃; for 5h;	Step 1: 4-(5-cyclopropoxy-2-methyl-4-nitrophenyl)-3,6-dihydro-2H-thiopyran <strong>[862129-81-5]3,6-dihydro-thiopyran-4-boronic acid pinacol ester</strong> (497mg, 2.2mmol), 1-bromo-5-cyclopropoxy-2-methyl-4-nitrobenzene (544mg, 2mmol), potassium carbonate (552mg, 4mg), [1,1'-bis (diphenylphosphino) ferrocene] dichloropalladium (146.4mg, 0.2mmol), water (1mL), 1,4-dioxane (10mL) were added to a 25ml reaction flask. The reaction mixture was heated up to 100 C and stirred for 5 hours. After completion of the reaction, the reaction solution was cooled down and added with ethyl acetate, filtered, and then washed with saturated brine. The aqueous phase was extracted with ethyl acetate, and the organic phase was dried, filtered, concentrated and purified by column chromatography (petroleum ether/ethyl acetate=10:1) to obtain the title compound (yellow oil, 480mg, 82%). (MS: [M+1] none)

Reference： [1]Patent: EP3150592,2017,A1 .Location in patent: Paragraph 0306; 0307; 0308

38
[ 862129-81-5 ]
[ 72254-60-5 ]
ethyl 2-amino-7-(3,6-dihydro-2H-thiopyran-4-yl)-5-oxo-5H-chromeno[2,3-b]pyridine-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With potassium phosphate; palladium diacetate; triphenylphosphine; In 1,4-dioxane; water; at 70 - 110℃; for 0.916667h;Inert atmosphere; Sealed tube;	A solution of tripotassium phosphate (701 mg, 3.3 mmol) in water (1.4 mL) was added to a nitrogen-degassed mixture of compound 1 (200 mg, 0.55 mmol), 2-(3,6-dihydro-2H-thiopyran-4-yl)-4,4,5,5-tetramethyl- 1,3 ,2-dioxaborolane (143 mg, 0.63 mmol),triphenylphosphine (72.2 mg, 0.28 mmol), Pd(Oac)2 (12.4 mg, 0.06 mmol) inp-dioxane (13.5mL). The reaction vessel was sealed with a screw cap and heated at 100 -110 C for 15 mmand then stirred at 70 C for 40 mm. After cooling, the mixture was concentrated and theresidue was distributed between dichloromethane and water. The organic phase was washedwith brine, dried (Na2504), and concentrated to a solid that was triturated in dichloromethaneand dried to give 72 (156 mg, 74%) as an off-white solid. ?H NMR (400 MHz, chloroformoe 9.15 (s, 1H), 8.37 (s, 1H), 8.20 (d, J= 2.4 Hz, 1H), 7.71 (dd, J= 8.7, 2.4 Hz, 1H), 7.46(d, J 8.7 Hz, 1H), 6.31 (dt, J 4.5, 2.6 Hz, 1H), 5.87 (s, 1H), 4.40 (q, J= 7.1 Hz, 2H), 3.38 (dt, J 4.6, 2.4 Hz, 2H), 2.92 (t, J 5.7 Hz, 2H), 2.81 - 2.73 (m, 2H), 1.44 (t, J= 7.1 Hz, 3H). MS TOFES: m/z 383.0 (M+H).
74%	With potassium phosphate; palladium diacetate; triphenylphosphine; In 1,4-dioxane; water; at 70 - 110℃; for 0.916667h;Sealed tube;	General procedure: (a) Suzuki couplings[1]General Procedure: A nitrogen-degassed solution of a potassium base in water was addedto a nitrogen-degassed suspension of substrate aryl bromide, alk-1-en-1-yl/cycloalk-1-en-1-yl boronic acid/pinacol ester, trialkyl-/triphenylphosphine, and palladium catalyst in anorganic solvent. The reaction vessel was sealed with a screw cap and heated for aspecified time, generally resulting in a clear orange solution. Workup was carried out byconcentrating the mixture to a residue that was diluted with water and extracted withdichloromethane. Further workup left a residue that was purified by trituration in anappropriate solvent or by silica gel chromatography.

Reference： [1]Patent: WO2017/132538,2017,A1 .Location in patent: Page/Page column 125; 126
[2]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 5443 - 5461

39
[ 862129-81-5 ]
ethyl 2-amino-5-oxo-7-(tetrahydro-2H-thiopyran-4-yl)-5H-chromeno[2,3-b]pyridine-3-carboxylate [ No CAS ]

Reference： [1]Patent: WO2017/132538,2017,A1
[2]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 5443 - 5461

40
[ 862129-81-5 ]
2-amino-5-oxo-7-(tetrahydro-2H-thiopyran-4-yl)-5H-chromeno[2,3-b]pyridine-3-carboxylic acid [ No CAS ]

Reference： [1]Patent: WO2017/132538,2017,A1
[2]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 5443 - 5461

41
[ 862129-81-5 ]
ethyl 2-amino-7-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-5-oxo-5H-chromeno[2,3-b]pyridine-3-carboxylate [ No CAS ]

Reference： [1]Patent: WO2017/132538,2017,A1
[2]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 5443 - 5461

42
[ 862129-81-5 ]
2-amino-7-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-5-oxo-5H-chromeno[2,3-b]pyridine-3-carboxylic acid [ No CAS ]

Reference： [1]Patent: WO2017/132538,2017,A1
[2]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 5443 - 5461

43
[ 862129-81-5 ]
[ 202865-85-8 ]
4-(4-bromo-3-methylphenyl)-3,6-dihydro-2H-thiopyran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; water; at 80 - 95℃;Inert atmosphere;	General procedure: General Procedure A: (0312) A mixture of an arylbromide or aryliodide (1 mmol), an arylboronic acid, aryldioxaborolane or bis(pinacolato)diboron (1.5 mmol), a palladium catalyst (0.1 mmol) and K2CO3 (2-3 mmol) was placed in a reaction vessel which was then thoroughly purged with argon. Dioxane (3 mL) and water (1.5 mL) were added, and the mixture was stirred at 80-95 C. for 1 to 4 h. After cooling to rt, the mixture was poured into EtOAc/H2O (1:1, 10 mL) and the aqueous layer was extracted with EtOAc (5 mL×2). The combined organic extracts were dried (Na2SO4), filtered and concentrated under reduced pressure. Purification of the resultant residue by silica gel chromatography (EtOAc/heptanes) afforded the desired biaryl product.

Reference： [1]Patent: US2017/291908,2017,A1 .Location in patent: Paragraph 0311; 0312; 0481

44
[ 862129-81-5 ]
[ 202865-85-8 ]
4-(4-bromo-3-methylphenyl)-3,6-dihydro-2H-thiopyran 1,1-dioxide [ No CAS ]

Reference： [1]Patent: US2017/291908,2017,A1

45
[ 862129-81-5 ]
4-chloro-6-(7-(difluoromethyl)-6-(1-methyl-1H-pyrazol-4-yl)-3,4-dihydroquinolin-1(2H)-yl)-1,3-dimethyl-1H-benzo[d]imidazol-2(3H)-one [ No CAS ]
6-(7-(difluoromethyl)-6-(1-methyl-1H-pyrazol-4-yl)-3,4-dihydroquinolin-1(2H)-yl)-4-(3,6-dihydro-2H-thiopyran-4-yl)-1,3-dimethyl-1H-benzo[d]imidazol-2(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With methanesulfonic acid(2-dicyclohexylphosphino-2?,4?,6?-triisopropyl-1,1?-biphenyl)[2-(2?-amino-1,1?-biphenyl)]palladium(II); sodium carbonate; XPhos; In tetrahydrofuran; water; at 80℃; for 16h;Inert atmosphere;	To a sol uti on of 4-chl oro-6-(7 -(difl uoromethy 1 )-6-(1-methy l-1H-pyrazol-4-y 1 )-3,4-15 dihydroquinolin-1(2H)-yl)-1,3-dimethyl-1H-benzo[d]imidazol-2(3H)-one (Example 33,500mg,1.09 mmol)in THF (10 mL)and water (2 mL)was added 2-(dicyclohexylphosphino)-2',4',6'-triisopropylbiphenyl (52 mg,0.11 mmol)and chloro(2-dicyclohexylphosphino-2',4',6'-trii-propyl-1,1'-biphenyl)(2'-amino-1,1'-biphenyl-2-yl)palladium(II)(43 mg,0.05 mmol),Na2C03(347 mg,3.28 mmol)and 2-(3,6-dihydro-2H-thiopyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-20 dioxaborolane (59 mg,0.26 mmol). The mixture was heated to 80 C for 16 h under a nitrogenatmosphere. After cooling the reaction to room temperature,water (50 mL)was added andextracted with EtOAc (30 mL x 3). The combined organic layers were washed with brine (30mL x 2),dried over anhydrous Na2S04,filtered and concentrated in vacuo. The crude residuewas purified by Prep-TLC (DCM I MeOH = 20: 1)to give the title compound (320 mg,56%)as25 a white solid. LCMS M/Z (M+H)522.

Reference： [1]Patent: WO2017/205536,2017,A2 .Location in patent: Page/Page column 158

46
[ 862129-81-5 ]
N-(4-(5-bromo-2-methoxyphenyl)-5-(thiophen-2-yl)-4H-1,2,4-triazol-3-yl)-2-(4-chlorophenyl)ethanesulfonamide [ No CAS ]
2-(4-chlorophenyl)-N-(4-(5-(3,6-dihydro-2H-thiopyran-4-yl)-2-methoxyphenyl)-5-(thiophen-2-yl)-4H-1,2,4-triazol-3-yl)ethanesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25.2%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate; In 1,4-dioxane; at 100℃; for 18h;	A mixture Example 133.0 (268 mg, 0.484 mmol), 2-(3,6-dihydro-2H-thiopyran- 4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (commercially available fromCombiblocks, CA, USA) (131 mg, 0.58 mmol), 2-dicyclohexylphosphino-2',6'- dimethoxy-1'1'-biphenyl (40 mg, 0.1 mmol), palladium (II) acetate (10.9 mg, 0.048 mmol) and potassium phosphate (154 mg, 0.73 mmol) in dioxane (6 mL) was combined in a 30 mL vial. The mixture was heated at 100 C for 18 h. The mixture was partitioned between EtOAc and water resulting in an emulsion. The emulsion layer was removed and filtered through a pad of Celite brand filter aid. The combined organic layers were washed with brine and evaporated to give a black solid. The material thus obtained was absorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (24 g), eluting with a gradient of 0% to 100% EtOAc in DCM, to provide the title compound, Example 248.0 (70 mg, 0.122 mmol, 25.2 % yield), as tan solid.1H NMR (400 MHz, DMSO-d6) delta 13.28 (s, 1 H) 7.71 (dd, J=5.09, 1.17 Hz, 1 H) 7.62 - 7.69 (m, 2 H) 7.34 (d, J=7.49 Hz, 2 H) 7.26 (d, J=7.63 Hz, 3 H) 7.05 (dd, J=4.99, 3.81 Hz, 1 H) 6.91 (dd, J=3.72, 1.17 Hz, 1 H) 6.29 (t, J=5.28 Hz, 1 H) 3.71 (s, 3 H) 3.12 - 3.29 (m, 4 H) 2.92 (t, J=8.12 Hz, 2 H) 2.75 - 2.84 (m, 2 H) 2.60 (br. s, 2 H). LCMS-ESI (pos.), m/z: 573.0 (M+H)+.

Reference： [1]Patent: WO2018/97945,2018,A1 .Location in patent: Paragraph 0452-0453

47
[ 862129-81-5 ]
N-(4-(5-bromo-2-methoxyphenyl)-5-(thiophen-2-yl)-4H-1,2,4-triazol-3-yl)-2-(4-chlorophenyl)ethanesulfonamide [ No CAS ]
2-(4-chlorophenyl)-N-(4-(5-(1,1-dioxido-3,6-dihydro-2H-thiopyran-4-yl)-2-methoxyphenyl)-5-(2-thiophenyl)-4H-1,2,4-triazol-3-yl)ethanesulfonamide [ No CAS ]

Reference： [1]Patent: WO2018/97945,2018,A1

48
[ 862129-81-5 ]
(3S,4S)-2-(1-benzyl-4-isobutylpyrrolidin-3-yl)-7-bromopyrrolo[2,1-f][1,2,4]triazin-4(3H)-one [ No CAS ]
2-((3S,4S)-1-benzyl-4-isobutylpyrrolidin-3-yl)-7-(3,6-dihydro-2H-thiopyran-4-yl)pyrrolo[2,1-f][1,2,4]triazin-4(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55.5%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium hydroxide; In 1,4-dioxane; water; at 100℃; for 8h;	The 2-(3S,4S)-1-benzyl-4-isobutyl-pyrrolidin-3-yl)-7-bromo-pyrrolo[2,1-f][1,2,4]triazin-4(3H)-ketone(1.0 g, 2.33 mmol) was dissolved in 1,4-dioxane (30 mL).2-(3,6-Dihydro-2H-thiopyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (632.3 mg, 2.796mmol),Potassium carbonate (644.1 mg, 4.66 mmol),Pd(dppf)Cl2 (2.05 g mg, 2.796 mmol) and water (15 mL).The reaction was heated to 100 C under reflux for 8 hours under nitrogen atmosphere.TLC monitoring reaction is over,The reaction solution is concentrated,Add in dichloromethane (150 mL) to dissolve.filter,The filtrate is concentrated,The crude product was obtained by silica gel column chromatography (DCM: MeOH=400: 1-100:1) to give the product 2-((3S,4S)-1-benzyl-4-isobutylpyrrolidin-3-yl)-7-(3,6-Dihydro-2H-thiopyran-4-yl)pyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (580 mg, yield: 55.5% ).

Reference： [1]Patent: CN108341819,2018,A .Location in patent: Paragraph 0171; 0173; 0175

49
[ 862129-81-5 ]
[ 57056-93-6 ]
2-(3,6-dihydro-2H-thiopyran-4-yl)-N-methylaniline [ No CAS ]

Reference： [1]Chinese Journal of Chemistry,2018,vol. 36,p. 909 - 915

50
[ 862129-81-5 ]
[ 57056-93-6 ]
1-(2-(3,6-dihydro-2H-thiopyran-4-yl)phenyl)-1-methyl-3-phenylurea [ No CAS ]

Reference： [1]Chinese Journal of Chemistry,2018,vol. 36,p. 909 - 915

51
[ 862129-81-5 ]
C₁₈H₁₂CeF₃ [ No CAS ]
C₁₁H₁₁FS [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 1188 - 1192
Angew. Chem.,2019,vol. 131,p. 1200 - 1204,5

52
[ 862129-81-5 ]
C₂₄H₁₅CeO₃ [ No CAS ]
3-(3,6-dihydro-2H-thiopyran-4-yl)benzofuran [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 1188 - 1192
Angew. Chem.,2019,vol. 131,p. 1200 - 1204,5

53
[ 862129-81-5 ]
C₁₅H₁₈CeN₃O₃ [ No CAS ]
4-(3,6-dihydro-2H-thiopyran-4-yl)-3,5-dimethylisoxazole [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 1188 - 1192
Angew. Chem.,2019,vol. 131,p. 1200 - 1204,5

54
[ 862129-81-5 ]
C₂₄H₂₁Ce [ No CAS ]
4-(1-phenylvinyl)-3,6-dihydro-2H-thiopyran [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 1188 - 1192
Angew. Chem.,2019,vol. 131,p. 1200 - 1204,5

55
[ 862129-81-5 ]
C₁₉H₁₈FN₅O₃S [ No CAS ]

Reference： [1]Patent: CN109575013,2019,A

56
[ 862129-81-5 ]
C₁₉H₂₀FN₅OS [ No CAS ]

Reference： [1]Patent: CN109575013,2019,A

57
[ 862129-81-5 ]
C₁₉H₂₀FN₅O₃S [ No CAS ]

Reference： [1]Patent: CN109575013,2019,A

58
[ 862129-81-5 ]
8-bromo-N-(furan-2-2-ylmethyl)-[1,2,4]triazolo[4,3-c]pyrimidin-5-amine [ No CAS ]
C₁₅H₁₅N₅OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With sodium 2'?(dicyclohexylphosphaneyl)?2,6?diisopropyl?[1,1'?biphenyl]?3?sulfonate; bis(eta3-allyl-mu-chloropalladium(II)); sodium carbonate; In 1,4-dioxane; water; at 20 - 90℃; for 0.833333h;Inert atmosphere;	Bromine 4-2 (58 mg, 0.2 mmol) was dissolved in 6 mL of 1,4-dioxane and 2 mL of a 2 M aqueous Na 2 CO 3 solution, and borate B-2 was added.(90mg, 0.4mmol),Ar substitution protection, stirring at room temperature for 10 minutes.Add 10% allyl palladium (II) dimer (7.3 mg, 0.02 mmol),20% 2'-dicyclohexylphosphino-2,6-dimethoxy-1,1'-biphenyl-3-sulfonic acid sodium hydrate(21.2 mg, 0.04 mmol), kept at 90 C for 40 minutes under Ar protection.After cooling, it was concentrated under reduced pressure and purified by column chromatography (DCM:MeOH = 20:1).The target compound E-Y5 is obtained,It was a white solid (37 mg, 60%).

Reference： [1]Patent: CN109575013,2019,A .Location in patent: Paragraph 0263-0266

59
[ 862129-81-5 ]
8-bromo-N-[(5-fluoro-2,3-dihydro-1-benzofuran-4-yl)methyl]-[1,2,4]triazolo[4,3-c]pyrimidin-5-amine [ No CAS ]
C₁₉H₁₈FN₅OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With sodium 2'?(dicyclohexylphosphaneyl)?2,6?diisopropyl?[1,1'?biphenyl]?3?sulfonate; bis(eta3-allyl-mu-chloropalladium(II)); sodium carbonate; In 1,4-dioxane; water; at 20 - 90℃; for 0.833333h;Inert atmosphere;	Bromine 4-1 (72 mg, 0.2 mmol)Dissolved in 6mL of 1,4-dioxane and 2mL of 2M Na2CO3 in water,Add borate B-2 (90 mg, 0.4 mmol), Ar replacement protection,Stir at room temperature for 10 minutes. Add 10% allyl palladium (II) dimer(7.3mg, 0.02mmol),20% 2'-dicyclohexylphosphino-2,6-dimethoxy-1,1'-biphenyl-3-sulfonic acid sodium hydrate(21.2 mg, 0.04 mmol), kept at 90 C for 40 minutes under Ar protection.After cooling, it was concentrated under reduced pressure and purified by column chromatography (DCM:MeOH = 20:1)The title compound E-Y2 was obtained as white solid (34 mg, 45%).

Reference： [1]Patent: CN109575013,2019,A .Location in patent: Paragraph 0251-0254

60
[ 862129-81-5 ]
4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-thiopyran 1,1-dioxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
27%	With oxone; In acetone; at 20 - 40℃; for 15h;	To a solution of <strong>[862129-81-5]2-(3,6-dihydro-2H-thiopyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane</strong> (500 mg, 2.21 mmol) in acetone (15 mL) was added oxone (5.9 g, 35.4 mmol) dropwise at room temperature. The resulting mixture was stirred at 40 C for 15 hours. After cooled to room temperature, the solvent was removed in vacuo. The residue was diluted with water and extracted with dichloromethane. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (petroleum ether: ethyl acetate = 1 : 1) to give 155 mg (27%) of the product as a white solid. 1H-NMR (400 MHz, CD3OD): delta [ppm] = 1.26 (s, 12H), 2.78-2.82 (m, 2H), 3.12 (t, 2H), 3.74- 3.75 (m, 2H), 6.38-6.40 (m, 1H). LC-MS (Analytical Method Q, 0-3.00 min 5-95% B): Rt = 1.04 min; MS (ESIpos): m/z = 259 [M+H]+.

Reference： [1]Patent: WO2019/81343,2019,A1 .Location in patent: Page/Page column 113

61
[ 862129-81-5 ]
2-[2-(1,1-dioxo-1,2,3,6-tetrahydro-1lambda6-thiopyran-4-yl)-5,8-dioxo-6-(propan-2-yl)-5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a]pyrrolo[3,4-d]pyrimidin-4-yl]-N-(5-fluoropyridin-2-yl)acetamide [ No CAS ]

Reference： [1]Patent: WO2019/81343,2019,A1

62
[ 862129-81-5 ]
2-[2-(1,1-dioxo-1lambda6-thian-4-yl)-5,8-dioxo-6-(propan-2-yl)-5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a]pyrrolo[3,4-d]pyrimidin-4-yl]-N-(5-fluoropyridin-2-yl)acetamide [ No CAS ]

Reference： [1]Patent: WO2019/81343,2019,A1

63
[ 862129-81-5 ]
1-methyl-3-(1-methyl-1H-pyrazol-4-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole [ No CAS ]
1-(3-bromo-1-iodo-5,6-dihydroimidazo[1,5-a]pyrazin-7(8H)-yl)ethanone [ No CAS ]
1-(3-(3,6-dihydro-2H-thiopyran-4-yl)-1-(1-methyl-3-(1-methyl-1H-pyrazol-4-yl)-1H-indazol-5-yl)-5,6-dihydroimidazo[1,5-a]pyrazin-7(8H)-yl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%		A mixture of the product from the previous step (200 mg, 541 mumol), Intermediate "F" (182.83 mg, 540.56 mumol), K3PO4 (344 mg, 1.62 mmol) and PdCl2(dppf) (45.05 mg, 54.06 mol) in 1,4-dioxane/H2O (3:1, 2 mL) was degassed and purged with N2. The mixture was stirred at 90 C. for 3 h, then concentrated under reduced pressure. To the residue was added 1,4-dioxane/H2O (3:1, 2 mL), <strong>[862129-81-5]2-(3,6-dihydro-2H-thiopyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane</strong> (170.73 mg, 754.96 moles), K2CO3 (223.6 mg, 1.62 mmol), and PdCl2(dppf) (44.94 mg, 53.93 mumol). The mixture was degassed and purged with N2, stirred at 100 C. for 1 h, then concentrated under reduced pressure. The residue was purified by SiO2 gel chromatography (25% to 100% EtOAc in petroleum ether) to give the title compound as a white solid (105 mg, 41%). MS (ES+): C25H27N7OS requires: 473, found: 474 [M+H]+.

Reference： [1]Patent: US2019/298729,2019,A1 .Location in patent: Paragraph 0569

64
[ 862129-81-5 ]
1-methyl-3-(1-methyl-1H-pyrazol-4-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole [ No CAS ]
3-bromo-1-iodo-N-methyl-6,8-dihydro-5H-imidazo[1,5-a]pyrazine-7-carboxamide [ No CAS ]
3-(3,6-dihydro-2H-thiopyran-4-yl)-N-methyl-1-(1-methyl-3-(1-methyl-1H-pyrazol-4-yl)-1H-indazol-5-yl)-5,6-dihydroimidazo[1,5-a]pyrazine-7(8H)-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%		A mixture of the product from the previous step (251 mg, 652 mumol), Intermediate "F" (220.50 mg, 651.94 mumol), K3PO4 (415 mg, 1.96 mmol) and PdCl2(dppf) (54.33 mg, 65.19 mumol) in 1,4-dioxane/H2O (3:1, 10 mL) was degassed and purged with N2. The mixture was stirred at 90 C. for 2 h, then concentrated under reduced pressure. To the residue was added 1,4-dioxane-H2O (3:1, 2 mL), <strong>[862129-81-5]2-(3,6-dihydro-2H-thiopyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane</strong> (205.75 mg, 909.78 mumol), K2CO3 (269 mg, 1.95 mmol) and PdCl2(dppf) (54.15 mg, 64.98 mumol). The mixture was degassed and purged with N2, and the mixture was heated at 100 C. for 5 h then concentrated under reduced pressure. The residue was purified by SiO2 gel chromatography (0% to 25% MeOH in CH2Cl2) to give the title compound as a brown solid (138 mg, 43%). MS (ES+): C25H28N8OS requires: 488, found: 489 [M+H]+.

Reference： [1]Patent: US2019/298729,2019,A1 .Location in patent: Paragraph 0576

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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. 862129-81-5 ] {[proInfo.proName]}

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[ 862129-81-5 ] Synthesis Path-Upstream 1~5

[ 862129-81-5 ] Synthesis Path-Downstream 1~64

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Organoboron

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