[ CAS No. 7205-46-1 ] {[proInfo.proName]}

Name: 7205-46-1|6-Chloro-1-methyl-1H-imidazo[4,5-c]pyridine|97%
Brand: Ambeed
SKU: A257329
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Quality Control of [ 7205-46-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 7205-46-1 ]

SDS Specification

Alternatived Products of [ 7205-46-1 ]

Product Details of [ 7205-46-1 ]

CAS No. :	7205-46-1	MDL No. :	MFCD16657937
Formula :	C₇H₆ClN₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RUVZGKRCLXIBFX-UHFFFAOYSA-N
M.W :	167.60	Pubchem ID :	13032381
Synonyms :

Calculated chemistry of [ 7205-46-1 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.14
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	43.8
TPSA :	30.71 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) :	-6.38 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.63
Log Po/w (XLOGP3) :	1.33
Log Po/w (WLOGP) :	1.62
Log Po/w (MLOGP) :	0.7
Log Po/w (SILICOS-IT) :	1.58
Consensus Log Po/w :	1.37

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.32
Solubility :	0.798 mg/ml ; 0.00476 mol/l
Class :	Soluble
Log S (Ali) :	-1.58
Solubility :	4.45 mg/ml ; 0.0265 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.71
Solubility :	0.328 mg/ml ; 0.00195 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.7

Safety of [ 7205-46-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 7205-46-1 ]

* 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 [ 7205-46-1 ]
Downstream synthetic route of [ 7205-46-1 ]

[ 7205-46-1 ] Synthesis Path-Upstream 1~8

1
[ 64-18-6 ]
[ 87034-76-2 ]
[ 7205-46-1 ]

Yield	Reaction Conditions	Operation in experiment
85%	at 100℃; for 3 h;	11.9.2 Typical example: Synthesis of 6-chloro-1-methyl-1H-imidazo[4,5-c]pyridine 2-Chloro-4-methylamino-5-aminopyridine (3.0 g, 19.0 mmol), trimethyl ortho formate (50 mL) and formic acid (1.0 mL) were stirred at 100 °C for 3 h. The reaction was cooled to ambient temperature and the solvents removed under vacuum. The residue was poured into NaHCO₃ solution and then extracted with AcOEt. The combined organic layers were washed with water, followed by brine and then dried over Na₂SO₄. The solvents were removed under vacuum to give a brown solid, which was purified by column chromatography (30percent AcOEt/DCM) to give the target product as a pale brown solid (2.7 g, 85percent). ¹H NMR (400 MHz, DMSO) δ (ppm): 8.75 (1 H, d, J = 0.89 Hz), 8.39 (1 H, s), 7.84 (1 H, d, J = 0.90 Hz), 3.86 (3 H, s). LC-MS R_t = 1.97 min; [M+H]⁺ 168.

Reference： [1] Patent: EP2818472, 2014, A1, . Location in patent: Paragraph 0154
[2] Patent: WO2013/117649, 2013, A1, . Location in patent: Paragraph 00265-00267

2
[ 87034-76-2 ]
[ 149-73-5 ]
[ 7205-46-1 ]

Yield	Reaction Conditions	Operation in experiment
38%	at 100℃; for 4 h;	Into a 100-mL round-bottom flask, was placed 6-chloro-4-N-methylpyridine-3,4-diamine (500 mg, 3.17 mmol, 1 equiv), trimethoxymethane (20 mL). The resulting solution was stirred for 4 h at 100 °C in an oil bath. The resulting mixture was concentrated under vacuum. The crude product was purified by Flash-Prep-HPLC A. This resulted in 200 mg (38percent) of the title compound as a solid. Analytical Data: LC-MS: (ES, m/z): 168 [M+l], R: 0.841 min.

Reference： [1] Patent: WO2017/181177, 2017, A1, . Location in patent: Paragraph 0556; 0564-0565

3
[ 64-18-6 ]
[ 87034-76-2 ]
[ 149-73-5 ]
[ 7205-46-1 ]

Reference： [1] Patent: WO2013/117645, 2013, A1, . Location in patent: Paragraph 00314

4
[ 1449506-71-1 ]
[ 7205-46-1 ]

Reference： [1] Patent: WO2013/117649, 2013, A1,
[2] Patent: WO2013/117645, 2013, A1,
[3] Patent: EP2818472, 2014, A1,
[4] Patent: WO2017/181177, 2017, A1,

5
[ 607373-83-1 ]
[ 7205-46-1 ]

Reference： [1] Patent: WO2013/117649, 2013, A1,
[2] Patent: WO2013/117645, 2013, A1,

6
[ 4487-56-3 ]
[ 7205-46-1 ]

Reference： [1] Patent: EP2818472, 2014, A1,
[2] Patent: WO2017/181177, 2017, A1,

7
[ 13091-23-1 ]
[ 7205-46-1 ]

Reference： [1] Patent: EP2818472, 2014, A1,

8
[ 850663-54-6 ]
[ 7205-46-1 ]

Reference： [1] Patent: EP2818472, 2014, A1,

[ 7205-46-1 ] Synthesis Path-Downstream 1~88

2
[ 1449515-92-7 ]
[ 7205-46-1 ]
[ 1449517-13-8 ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; XPhos; In 1,4-dioxane; at 120.0℃; for 5h;Inert atmosphere;	A degassed mixture of the amine (1 eq, 200 mg), 6-chloro-l -methyl- lH-imidazo[4,5- c]pyridine (1 eq, 144 mg), Cs2C03 (2 eq, 561 mg), Xphos (0,15 eq, 62 mg) and Pd2(dba)3 (0,1 eq, 79 mg) in dry 1.4-dioxane (5 mL) was heated at 120C for 5 h. Water (10 mL) was added and the reaction mixture was extracted with EtOAc (3 x). The combined organics were dried, concentrated and the residue was purified by silica chromatography (EtOAc/cyclohexane; 0:100 to 50:50) to give the desired compound.

Reference： [1]Patent: WO2013/117649,2013,A1 .Location in patent: Paragraph 00348

3
[ 1449515-93-8 ]
[ 7205-46-1 ]
[ 1449514-98-0 ]

Yield	Reaction Conditions	Operation in experiment
	With palladium diacetate; caesium carbonate; XPhos; In toluene; at 100.0℃; for 16h;	A mixture of the aniline (1.1 eq, 106 mg), 6-chloro-l -methyl- lH-imidazo[4,5-c]pyridine (1 eq, 100 mg), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.3 eq, 86 mg), palladium(II) acetate (0.1 eq, 13.5 mg) and CS2CO3 (3 eq, 391 mg) in toluene (5 mL) was stirred at 100 C for 16 h. The reaction mixture was filtered on Celite, the filtrate concentrated and the residue purified by silica chromatography (EtOAc /cyclohexane; 0:100 to 100:0) to give the desired compound.

Reference： [1]Patent: WO2013/117649,2013,A1 .Location in patent: Paragraph 0002

4
[ 1449515-93-8 ]
[ 7205-46-1 ]
[ 1449515-01-8 ]

Reference： [1]Patent: WO2013/117649,2013,A1

5
[ 64-18-6 ]
[ 87034-76-2 ]
[ 7205-46-1 ]

Yield	Reaction Conditions	Operation in experiment
85%	With trimethyl orthoformate; at 100.0℃; for 3h;	11.9.2 Typical example: Synthesis of 6-chloro-1-methyl-1H-imidazo[4,5-c]pyridine 2-Chloro-4-methylamino-5-aminopyridine (3.0 g, 19.0 mmol), trimethyl ortho formate (50 mL) and formic acid (1.0 mL) were stirred at 100 C for 3 h. The reaction was cooled to ambient temperature and the solvents removed under vacuum. The residue was poured into NaHCO3 solution and then extracted with AcOEt. The combined organic layers were washed with water, followed by brine and then dried over Na2SO4. The solvents were removed under vacuum to give a brown solid, which was purified by column chromatography (30% AcOEt/DCM) to give the target product as a pale brown solid (2.7 g, 85%). 1H NMR (400 MHz, DMSO) delta (ppm): 8.75 (1 H, d, J = 0.89 Hz), 8.39 (1 H, s), 7.84 (1 H, d, J = 0.90 Hz), 3.86 (3 H, s). LC-MS Rt = 1.97 min; [M+H]+ 168.
	With orthoformic acid triethyl ester; at 100.0℃; for 4h;	To a stirred solution of 6-Chloro-N-methyl-pyridine-3, 4-diamine (22 mmol) in trimethyl orthoformate (25 mL) was added formic acid (1 mL) and was heated ay 100C for nearly 4 h when TLC showed the completion of reaction. The reaction was allowed to cool to room temperature and water (50 mL) was added and the mixture was extracted with ethyl acetate (4x50 mL), the combined organic layers were washed with aq. NaHC03 solution, dried over anhydrous sodium sulphate and concentration under reduced pressure gave the desired product Intermediate 2. [00266] 'H-NMR (400 MHz, DMSO-i): delta 3.84 (s, 3H), 7.83 (s, 1H), 8.39 (s, 1H), 8.74 (s, 1H). [00267] Mass (M+l): w/z 168.

Reference： [1]Patent: EP2818472,2014,A1 .Location in patent: Paragraph 0154
[2]Patent: WO2013/117649,2013,A1 .Location in patent: Paragraph 00265-00267

6
[ 1449515-95-0 ]
[ 7205-46-1 ]
[ 1449515-96-1 ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In 1,4-dioxane; at 110.0℃; for 16h;	A degassed mixture of the amine (1 eq, 236 mg), 6-chloro-l -methyl- lH-imidazo[4,5- c]pyridine (1 eq, 150 mg), Cs2C03 (2 eq, 583 mg), BINAP (0.3 eq, 167 mg) and Pd2(dba)3 (0.1 eq, 82 mg) in dry 1.4-dioxane (3 mL) was heated at 110C for 16 h. Water (10 mL) was added and the reaction mixture was extracted with EtOAc (3 x). The combined organics was dried, concentrated and the residue was purified by silica chromatography (MeOH/DCM; 0:100 to 5:95) to give the desired compound

Reference： [1]Patent: WO2013/117649,2013,A1 .Location in patent: Paragraph 0005

7
[ 1449515-95-0 ]
[ 7205-46-1 ]
[ 1449514-99-1 ]

Reference： [1]Patent: WO2013/117649,2013,A1

8
[ 39211-56-8 ]
[ 7205-46-1 ]
[ 1449515-02-9 ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; XPhos; In N,N-dimethyl-formamide; at 110.0℃; for 18h;	A degassed mixture of the amine (1 eq, 28 mg), 6-chloro-l-methyl-lH-imidazo[4,5- c]pyridine (1 eq, 27 mg), CS2CO3 (2.5 eq, 132 mg), Xphos (0.3 eq, 23 mg) and Pd2(dba)3 (0.1 eq, 15 mg) in dry DMF (1 mL) was heated at 110C for 18 h. Water was added and the reaction mixture was extracted with EtOAc (3 x). The combined organics were dried, concentrated and the residue was purified by silica chromatography (MeOH/EtOAc; 0:100 to 10:90) to give the desired compound

Reference： [1]Patent: WO2013/117649,2013,A1 .Location in patent: Paragraph 0013

9
[ 1449515-99-4 ]
[ 7205-46-1 ]
[ 1449515-03-0 ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In N,N-dimethyl-formamide; at 100.0℃; for 18h;	A degassed mixture of the amine (1 eq, 67 mg), 6-chloro-l-methyl-lH-imidazo[4,5- c]pyridine (1 eq, 59 mg), Cs2C03 (2.5 eq, 288 mg), BetaGammaNuAlphaRho (0.3 eq, 66 mg) and Pd2(dba)3 (0.1 eq, 32 mg) in dry DMF (2 mL) was heated at 100C for 18 h. Water was added and the reaction mixture was extracted with EtOAc (3 x). The combined organics were dried, concentrated and the residue was purified by prep arative HPLC give the desired compound.

Reference： [1]Patent: WO2013/117649,2013,A1 .Location in patent: Paragraph 0015

10
[ 1449516-02-2 ]
[ 7205-46-1 ]
[ 1449515-06-3 ]

Yield	Reaction Conditions	Operation in experiment
	With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 110.0℃; for 18h;	A degassed mixture of the amine (1.1 eq, 119 mg), 6-chloro-l -methyl- lH-imidazo[4,5- c]pyridine (1 eq, 98 mg), CS2CO3 (2 eq, 378 mg), Xphos (0.3 eq, 83 mg) and palladium(II) acetate (0.1 eq, 13 mg) in dry toluene (5 mL) was heated at 110C for 18 h. The mixture was filtered through Celite and concentrated. The residue was purified by silica chromatography (MeOH/DCM; 0:100 to 10:90) to give the desired compound.

Reference： [1]Patent: WO2013/117649,2013,A1 .Location in patent: Paragraph 0025

11
[ 59820-84-7 ]
[ 7205-46-1 ]
[ 1449514-86-6 ]

Yield	Reaction Conditions	Operation in experiment
	With dibenzylideneacetone bis(triphenylphiosphine) palladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate; In N,N-dimethyl-formamide; at 120.0℃; for 16h;	A mixture of 6-chloro-l -methyl- lH-imidazo[4,5-c]pyridine (84 mg, 0.5 mmol), 7-methyl- 2,3-dihydrobenzo[6][l,4]dioxin-6-amin e ( 1 24 mg , 0 . 7 5 mm o l ) , d ib e nzy l i d en e ac e t o n e bis(triphenylphiosphine) palladium (0) (23 mg, 0.025 mmol), 4,5-bis(diphenylphosphino)-9,9- dimethylxanthene (29 mg, 0.05 mmol), sodium teri-butoxide (72 mg, 0.75 mmol) and DMF (1.5 mL) was stirred at 120 C for 16 h. The reaction mixture was allowed to cool to room temperature, filtered and the solvent removed in vacuo. The crude product was purified by preparative HPLC to give the desired compound. [00284] NMR delta (ppm)(CHCl3-d): 8.64 (1 H, s, ArH), 7.68 (1 H, s, ArH), 6.93 (1 H, s, ArH), 6.79 (1 H, m, ArH), 6.39 (1 H, s, NH), 6.34 (1 H, s, ArH), 4.26-4.29 (4 H, m, CH2), 3.67 (3 H, s, CH3), 2.17 (3 H, s, CH3). [00285] LCMS (1 Ocm ESI Bicarb MeCN) tR 2.48 (min) m/z 297 (MH+).

Reference： [1]Patent: WO2013/117649,2013,A1 .Location in patent: Paragraph 00283-00285

12
[ 578-54-1 ]
[ 7205-46-1 ]
[ 1449515-21-2 ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 110.0℃; for 16h;Inert atmosphere;	The corresponding amine (0.58 mmol) is added to a solution of 6-chloro-l -methyl- 1H- imidazo[4,5-c]pyridine (intermediate 2) (0.45 mmol) and cesium carbonate (0.62 mmol) in dioxane (3 mL). Degassing is done for 5 min, followed by addition of a solution previously sonicated for 10 min of Xantphos (0.06 eq), Pd2(dba)3 (0.03eq) in dioxane (1 mL) under nitrogen. The reaction heated at 110C for 16 h. After completion, water and DCM are added and this mixture is filtered through a phase separator. The organic layers are concentrated under reduced pressure. The crude product is purified by preparative HPLC to afford the expected compound.
	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 110.0℃;Inert atmosphere;	In a microwave vial was introduced Intermediate 2 (150mg, 0.895mmol), the 2-ethyl aniline (0.14mL, 1.163 mmol) and CS2CO3 (408.2mg, 1.253mmol) in 1,4-dioxane (4 mL). The reaction mixture was degassed with N2 during 10 min. A mixture of Pd2(dba)3 (24.6mg, 0.027mmol) and xantphos (31.1mg, 0.054mmol) in 1,4-dioxane (2 mL) was sonicated and then added under N2 to the reaction mixture. The reaction mixture was degassed with N2 for another 10 min. The vial was capped and the mixture was stirred at 110C overnight. The reaction mixture was concentrated in vacuo, the crude was then purified by flash column chromatography on silica gel using DCM / MeOH (gradient 100 to 95/5) afforded the (2-Ethyl-phenyl)-(l-methyl-lH-imidazo[4,5-c]pyridin-6-yl)-amine. LC-MS : [M+H]+ : 253.33.

Reference： [1]Patent: WO2013/117649,2013,A1 .Location in patent: Page/Page column 56; 89
[2]Patent: WO2013/117645,2013,A1 .Location in patent: Paragraph 00397

13
[ 67159-81-3 ]
[ 7205-46-1 ]
[ 1449515-47-2 ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In 1,4-dioxane; for 15h;Reflux;	To a solution of 6-chloro-l -methyl- lH-imidazo[4,5-c]pyridine (intermediate 2) (14.9 mmol) in dioxane (100 mL) is added the corresponding aniline (22.4 mmol), cesium carbonate (22.4 mmol), BINAP (0.9mmol) and tris(dibenzylideneacetone)dipalladium (0.45 mmol). The reaction mixture is refluxed for 15 h, filtrated on celite, evaporated to dryness and purified on silica gel to give the expected product.

Reference： [1]Patent: WO2013/117649,2013,A1 .Location in patent: Paragraph 00273; 0059

14
[ 1449516-27-1 ]
[ 7205-46-1 ]
[ 1449515-71-2 ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; XPhos; In 1,4-dioxane; at 100.0℃; for 24h;Inert atmosphere;	To stirred degassed (N2) 1,4-dioxane (10 mL) is added 4-Aryl-2-Ethylaniline obtained in step i) (2.00 mmol), 6-chloro- 1 -methyl- lH-imidazo[4,5-c] p yri d i n e ( 3 03 m g , 1 . 8 mm o l ) , tris(dibenzylideneacetone)dipalladium(0) (82 mg, 0.09 mmol), 2-dicyclohexylphosphino-2',4',6'- triisopropylbiphenyl (86 mg, 0.18 mmol) and sodium teri-butoxide (260 mg, 2.7 mmol). The reaction mixture is heated to 100C for 1 d, cooled to room temperature, filtered through Celite and washed through with DCM. The reaction mixture is washed with water and the layers are separated and the aqueous layer further extracted with DCM. The organics are combined, dried (hydrophobic filter) and concentrated in vacuo and the resulting residue is purified by column chromatography using silica gel. The fractions containing product are combined and concentrated in vacuo to give the final product (2- Ethyl-4-aryl-phenyl)-(3-methyl-3H-benzoimidazol-5-yl)-amine.

Reference： [1]Patent: WO2013/117649,2013,A1 .Location in patent: Paragraph 00282; 0059

15
[ 1449515-86-9 ]
[ 7205-46-1 ]
[ 1449514-88-8 ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate; In 1,4-dioxane; at 90.0℃; for 16h;	A mixture of 6-chloro-l-methyl-lH-imidazo[4,5-c]pyridine (100 mg, 0.60 mmol), 7-ethyl- 2,3-dihydrobenzo[6][l,4]dioxin-6-amine (160 mg, 0.90 mmol), tris(dibenzylideneacetone)- dipalladium(O) (27 mg, 0.03 mmol), sodium tert-butoxide (86 mg, 0.90 mmol), 4,5- bis(diphenylphosphino)-9,9-dimethylxanthene (34 mg, 0.06 mmol) and dioxane (5 mL) was stirred at 90 C for 16 h. The reaction mixture was allowed to cool to room temperature, filtered and concentrated in vacuo. The crude product was purified by column chromatography using silica gel and eluting with 0 - 10% MeOH in DCM to give the desired compound. [00295] NMR delta (ppm)(DMSO-d6): 8.43 (1 H, d, ArH), 7.98 (1 H, s, ArH), 7.69 (1 H, s, ArH), 6.88 (1 H, s, ArH), 6.73 (1 H, s, NH), 6.44 (1 H, d, ArH), 4.22 (4 H, s, CH2), 3.65 (3 H, s, CH3), 2.56- 2.50 (2 H, q, CH2), 1.06 (3 H, t, CH3). [00296] LCMS (15cm_Formic_ASCENTIS_HPLC_CH3CN) tR 7.32 (min) m/z 311 (MH+).

Reference： [1]Patent: WO2013/117649,2013,A1 .Location in patent: Paragraph 00294

16
[ 607373-83-1 ]
[ 7205-46-1 ]

Reference： [1]Patent: WO2013/117649,2013,A1
[2]Patent: WO2013/117645,2013,A1

17
[ 7205-46-1 ]
2-ethyl-4-fluoroaniline [ No CAS ]
[ 1449514-89-9 ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate; In 1,4-dioxane; at 90.0℃; for 24h;Inert atmosphere;	To stirred degassed (N2 (g)) dioxane (3 mL) was added 6-chloro-l-methyl-lH-imidazo[4,5- c]pyridine (219 mg, 1.31 mmol), 2-ethyl-4-fluoroaniline (200 mg, 1.44 mmol), sodium-tert-butoxide (189 mg, 1.97 mmol), tris(dibenzylideneacetone)dipalladium(0) (60 mg, 0.066 mmol) and 4,5- bis(diphenylphosphino)-9,9-dimethylxanthene (76 mg, 0.131 mmol). The reaction mixture was heated to 90C for 1 d. The reaction mixture was filtered through celite, washed through with EtOAc and partitioned between EtOAc and water. The layers were separated and the aqueous layer extracted with EtOAc, the organics were combined and dried (MgSO i), filtered and concentrated in vacuo to give the desired compound. For analytical purpose, a 100 mg sample was purified by preparative HPLC to give the desired compound. [00301] NMR delta (ppm)(DMSO-d6): 8.45 (1 H, s, NH), 8.01 (1 H, s, ArH), 7.87 (1 H, s, ArH), 7.46- 7.39 (1 H, m, ArH), 7.10-7.05 (1 H, m, ArH), 7.03-6.96 (1 H, m, ArH), 6.55 (1 H, d, ArH), 3.67 (3 H, s, CH3), 2.67-2.57 (2 H, m, CH2), 1.16-1.07 (3 H, m, CH3). [00302] LCMS (lOcm ESCI Bicarb MeCN) tR 2.80 (min) m/z 271 (MH+).
	With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate; In 1,4-dioxane; at 90.0℃; for 24h;Inert atmosphere;	To stirred degassed (N2) 1,4-dioxane (3 mL) was added 6-chloro-l -methyl- lH-imidazo[4,5- c]pyridine (219 mg, 1.31 mmol), 2-ethyl-4-fluoroaniline (200 mg, 1.44 mmol), sodium-fert-butoxide (189 mg, 1.97 mmol), tris(dibenzylideneacetone)dipalladium(0) (60 mg, 0.066 mmol) and 4,5- bis(diphenylphosphino)-9,9-dimethylxanthene (76 mg, 0.131 mmol). The reaction mixture was heated to 90C for 1 d. The reaction mixture was filtered through Celite, washed through with EtOAc and partitioned between EtOAc and water. The layers were separated and the aqueous layer extracted with EtOAc, the organics were combined and dried (MgSO i), filtered and concentrated in vacuo to give the desired compound, which was used in the next step without further purification. A 100 mg sample was purified by preparative HPLC to give the desired compound. NMR delta (ppm)(DMSO-d6): 8.45 (1 H, s, NH), 8.01 (1 H, s, ArH), 7.87 (1 H, s, ArH), 7.46-7.39 (1 H, m, ArH), 7.10-7.05 (1 H, m, ArH), 7.03-6.96 (1 H, m, ArH), 6.55 (1 H, d, ArH), 3.67 (3 H, s, CH3), 2.67-2.57 (2 H, m, CH2), 1.16-1.07 (3 H, m, CH3). LCMS (lOcm ESCI Bicarb MeCN) Rt 2.80 (min) m/z 271 (MH+).

Reference： [1]Patent: WO2013/117649,2013,A1 .Location in patent: Paragraph 00300-00302
[2]Patent: WO2013/117645,2013,A1 .Location in patent: Paragraph 00405

18
[ 1016502-66-1 ]
[ 7205-46-1 ]
[ 1449514-90-2 ]

Yield	Reaction Conditions	Operation in experiment
		6-Chloro-l-methyl-lH-imidazo[4,5-c]pyridine (2.52 g, 0.015 mol) was stirred with 4,5- bis(diphenylphosphino)-9,9-dimethylxanthene (0.86 g, 0.0015 mol), sodium-tert-butoxide (2.16 g, 0.0225 mol) and 4-(4-methoxybenzyloxy)-2-methylaniline (3.68 g, 0.015 mol) in dry dioxane (50 mL) under N2 (g) for 30 minutes. Tris(dibenzylideneacetone)dipalladium(0) (0.68 g, 0.00075 mol) was added and the mixture was stirred at 100C for 4.5 h. The mixture was concentrated in vacuo and the residue was treated with water (50 mL) and extracted into EtOAc (2 x 300 mL). The combined extracts were washed with brine, dried (MgSO i), filtered and concentrated in vacuo to give a solid which was recrystalised from isopropanol to give the desired compound. [00306] NMR delta (ppm)(DMSO-d6): 8.43 (1 Eta, d, ArH), 7.98 (1 H, s, NH), 7.75 (1 H, s, ArH), 7.39 (2 H, d, ArH), 7.27 (1 H, d, ArH), 7.00-6.90 (3 H, m, ArH), 6.82 (1 H, dd, ArH), 6.38 (1 H, d, ArH), 5.00 (2 H, s, CH), 3.77 (3 H, s, CH3), 3.64 (3 H, s, CH3), 2.17 (3 H, s, CH3).
	With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate; In 1,4-dioxane; at 100.0℃; for 4.5h;Inert atmosphere;	6-Chloro-l-methyl-lH-imidazo[4,5-c]pyridine (2.52 g, 0.015 mol) was stirred with 4,5- bis(diphenylphosphino)-9,9-dimethylxanthene (0.86 g, 0.0015 mol), sodium tert-butoxide (2.16 g, 0.0225 mol) and 4-(4-methoxybenzyloxy)-2-methylaniline (3.68 g, 0.015 mol) in dry 1,4-dioxane (50 mL) under N2 (g) for 30 min. Tris(dibenzylideneacetone)dipalladium(0) (0.68 g, 0.00075 mol) was added and the mixture was stirred at 100C for 4.5 h. The mixture was concentrated in vacuo and the residue was treated with water (50 mL) and extracted into EtOAc (2 x 300 mL). The combined extracts were washed with brine, dried (MgSO i), filtered and concentrated in vacuo to give a brown solid which was recrystalised from isopropanol to give the desired compound. NMR delta (ppm)(DMSO-d6): 8.43 (1 H, d, ArH), 7.98 (1 H, s, NH), 7.75 (1 H, s, ArH), 7.39 (2 H, d, ArH), 7.27 (1 H, d, ArH), 7.00-6.90 (3 H, m, ArH), 6.82 (1 H, dd, ArH), 6.38 (1 H, d, ArH), 5.00 (2 H, s, CH), 3.77 (3 H, s, CH3), 3.64 (3 H, s, CH3), 2.17 (3 H, s, CH3). LCMS (15cm_Bicarb_GeminiNX_HPLC_MeCN) Rt 9.63 (min) m/z 375 (MH+).

Reference： [1]Patent: WO2013/117649,2013,A1 .Location in patent: Paragraph 00305
[2]Patent: WO2013/117645,2013,A1 .Location in patent: Paragraph 00410

19
[ 40401-45-4 ]
[ 7205-46-1 ]
[ 1449514-91-3 ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; XPhos; In 1,4-dioxane; at 90.0℃; for 6h;Inert atmosphere;	To a stirred solution of degassed dioxane (2 mL) was added 6-chloro-l -methyl- 1H- imidazo[4,5-c]pyridine (300 mg, 1.78 mmol), 7-amino-6-chloro-2H-benzo[6][l,4]oxazin-3(4H)-one (426 mg, 2.13 mmol), tris(dibenzylideneacetone)dipalladium(0) (81 mg, 0.089 mmol), 2- dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (170 mg, 0.356 mmol) and sodium teri-butoxide (258 mg, 2.67 mmol) and the resulting mixture was heated to 90C for 6 h. The reaction mixture was cooled to room temperature, filtered through a PL-Thiol MP SPE+ column (pre-conditioned with 1 mL MeOH) using MeOH (3 x 2 mL) to wash the column. The combined organics were concentrated in vacuo and the resulting residue was purified by preparative HPLC to give the desired compound. [00308] NMR delta (ppm)(DMSO-d6): 10.72 (1 H, s, NH), 8.57 (1 H, d, ArH), 8.14 (1 H, s, ArH), 8.06 (1 H, s, NH), 7.65 (1 H, s, ArH), 7.03 (1 H, d, ArH), 6.98 (1 H, s, ArH), 4.61 (2 H, s, CH2), 3.76 (3 H, s, CH3). [00309] LCMS (1 Ocm ESI Bicarb MeCN) tR 2.62 (min) m/z 330 (MH+).

Reference： [1]Patent: WO2013/117649,2013,A1 .Location in patent: Paragraph 00307-00309

20
[ 1449515-88-1 ]
[ 7205-46-1 ]
[ 1449514-92-4 ]

Yield	Reaction Conditions	Operation in experiment
		6-Chloro-l-methyl-lH-imidazo[4,5-c]pyridine (0.835 g, 5 mmol) was stirred with 4,5- bis(diphenylphosphino)-9,9-dimethylxanthene (0.29 g, 5 mmol), sodium fert-butoxide (0.73 g, 7.5 mol) and 7-amino-4-(4-methoxybenzyl)-2H-benzo[^][l,4]oxazin-3(4H)-one (1 .42 g, 5 mmol) in degassed dioxane (40 mL) under N2 (g) for 30 min. Tris(dibenzylideneacetone)dipalladium(0) (0.23 g, 0.25 mmol) was added and the reaction was stirred at 100 C for 5 h. The mixture was concentrated in vacuo and the residue was treated with water (50 mL) and extracted into EtOAc (2 x 200 mL). The combined extracts were washed with brine, dried (MgSO i), filtered and concentrated in vacuo to give the desired compound. For analytical purpose, a sample of this material (100 mg) was purified by preparative HPLC to give the desired compound. [00315] NMR delta (ppm)(DMSO-d6): 8.85 (1 H, s, NH), 8.55 (1 H, d, ArH), 8.08 (1 H, s, ArH), 7.43 (1 H, d, ArH), 7.23 (2 H, d, ArH), 7.09 (1 H, dd, ArH), 6.98-6.83 (3 H, m, ArH), 6.83 (1 H, d, ArH), 5.06 (2 H, s, CH2), 4.73 (2 H, s, CH2), 3.72 (6 H, d, CH3). [00316] LCMS (lOcm ESCI Bicarb MeCN) tR 3.16 (min) m/z 416 (MH+).

Reference： [1]Patent: WO2013/117649,2013,A1 .Location in patent: Paragraph 00314-00316

21
[ 1449506-71-1 ]
[ 7205-46-1 ]

Reference： [1]Patent: WO2013/117649,2013,A1
[2]Patent: WO2013/117645,2013,A1
[3]Patent: EP2818472,2014,A1
[4]Patent: WO2017/181177,2017,A1

22
[ 1369892-98-7 ]
[ 7205-46-1 ]
[ 1449514-93-5 ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate; In 1,4-dioxane; at 100.0℃; for 7h;Inert atmosphere;	A mixture of 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.08 g), 6-chloro-l-methyl- lH-imidazo[4,5-c]pyridine (0.23 g, 0.0014 mol), 3-amino-4-ethyl-N,N-dimethylbenzamide (0.27 g, 0.0014 mol) and sodium tert-butoxide (0.20 g, 0.0021 mol) in 1,4-dioxane (15 mL) was stirred under N2 for 20 min. Tris(dibenzylideneacetone)dipalladium(0) (0.06 g) was added and the mixture was stirred at 100C for 7 h. The reaction mixture was concentrated in vacuo and the residue was treated with water and extracted into EtOAc. The organics were washed with brine, dried (MgSO i) and concentrated in vacuo to give the desired compound. For analytical purpose, a 60 mg sample was further purified by preparative HPLC to give the desired compound. [00324] NMR delta (ppm)(CHCl3-d): 8.69 (1 H, d, ArH), 7.71 (1 H, s, ArH), 7.52 (1 H, d, ArH), 7.32 (1 H, m, ArH), 7.16 (1 H, dd, ArH), 6.63 (1 H, d, ArH), 6.36 (1 H, s, NH), 3.68 (3 H, s, CH3), 3.09 (3 H, s, CH3), 3.03 (3 H, s, CH3), 2.69 (2 H, q, CH2), 1.24 (3 H, t, CH3). [00325] LCMS (lOcm ESCI Formic MeCN) tR 2.21 (min) m/z 324 (MH+).
	With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate; In 1,4-dioxane; at 100.0℃; for 7h;	A mixture of 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.08 g), 6-chloro-l-methyl- lH-imidazo[4,5-c]pyridine (0.23 g, 0.0014 mol), 3-amino-4-ethyl-N,N-dimethylbenzamide (0.27 g, 0.0014 mol) and sodium tert-butoxide (0.20 g, 0.0021 mol) in 1,4-dioxane (15 mL) was stirred under N2 for 20 min. Tris(dibenzylideneacetone)dipalladium(0) (0.06 g) was added and the mixture was stirred at 100C for 7 h. The reaction mixture was concentrated in vacuo and the residue was treated with water and extracted into EtOAc. The organics were washed with brine, dried (MgS04) and concentrated in vacuo to give the desired compound. NMR delta (ppm)(CHCl3-d): 8.69 (1 H, d, ArH), 7.71 (1 H, s, ArH), 7.52 (1 H, d, ArH), 7.32 (1 H, m, ArH), 7.16 (1 H, dd, ArH), 6.63 (1 H, d, ArH), 6.36 (1 H, s, NH), 3.68 (3 H, s, CH3), 3.09 (3 H, s, CH3), 3.03 (3 H, s, CH3), 2.69 (2 H, q, CH2), 1.24 (3 H, t, CH3). LCMS (lOcm ESCI Formic MeCN) Rt 2.21 (min) m/z 324 (MH+).

Reference： [1]Patent: WO2013/117649,2013,A1 .Location in patent: Paragraph 00323-00325
[2]Patent: WO2013/117645,2013,A1 .Location in patent: Paragraph 00432

23
[ 5129-22-6 ]
[ 7205-46-1 ]
[ 1449514-94-6 ]

Yield	Reaction Conditions	Operation in experiment
	With dibenzylideneacetone bis(triphenylphiosphine) palladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate; In N,N-dimethyl-formamide; at 120.0℃; for 16h;	A mixture of 6-chloro-l-methyl-lH-imidazo[4,5-c]pyridine (intermediate 2) (84 mg, 0.5 mmol), 7-methyl-2,3-dihydrobenzo[6][l,4]dioxin-6-amine ( 1 .5 eq. ) , dib enzylidene ac etone bis(triphenylphiosphine) palladium (0) (5mol.%), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (10 mol.%), sodium tert-butoxide (1.5 eq.) and DMF (0.33 M) is stirred at 120 C for 16 h. The reaction mixture is allowed to cool to room temperature, filtered and the solvent removed in vacuo. The crude product is purified by preparative HPLC to afford the desired product. (4-ethyl-3-(l-methyl-lH-imidazo[4,5-c]pyridin-6-ylamino)phenyl)methanol was obtained by reacting (3-Amino-4-ethylphenyl)methanol with 6-chloro-l-methyl-lH-imidazo[4,5-c]pyridine according to method A" described above
	With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate; In 1,4-dioxane; at 100.0℃; for 7h;Inert atmosphere;	To stirred degassed (N2) 1,4-dioxane (30 mL) was added (3-amino-4-ethylphenyl)MeOH (440 mg, 2.90 mmol), 6-chloro-l -methyl-lH-imidazo[4,5-c] pyridine (480 mg, 2.9 mmo l) , tris(dibenzylideneacetone)dipalladium(0) (0.12 mg, 0.145 mmol), 4,5-bis(diphenylphosphino)-9,9- dimethylxanthene (160 mg, 0.29 mmol) and sodium tert-butoxide (690 mg, 0.725 mmol). The reaction mixture was heated to 100 C for 7 h, cooled to room temperature, concentrated in vacuo and ethyl acetate and water were added. The ethyl acetate was separated, dried (MgSO i), filtered and concentrated in vacuo. The residue was dissolved in MeOH and loaded onto a 20 g SCX cartridge which was washed with MeOH and eluted with dilute ammonia in MeOH to give the desired compound.

Reference： [1]Patent: WO2013/117649,2013,A1 .Location in patent: Paragraph 00274; 00330
[2]Patent: WO2013/117645,2013,A1 .Location in patent: Paragraph 00443

24
[ 24812-93-9 ]
[ 7205-46-1 ]
[ 1449668-98-7 ]

Yield	Reaction Conditions	Operation in experiment
		6-Chloro-l-methyl-lH-imidazo[4,5-c]pyridine (1.67 g, 0.01 mol), methyl 3-amino-4- ethylbenzoate (2.15 g, 0.012 mol) and caesium carbonate (4.56 g, 0.014 mol) were stirred together in tert-butanol (20 mL) under N2 for 20 min. Chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2'-4'-6'- tri-i-propyl-l,l'-biphenyl][2-(2-aminoethyl)phenyl] palladium(II) (BrettPhos Palladacycle) (0.079 g, 1 mol%) and 2-dicyclohexylphosphino-2',6'-di-iso-propoxy-l,l'-biphenyl (RuPhos) (0.046 g, 1 mol%) were added and the mixture was refluxed for 5 h. The reaction mixture was evaporated in vacuo and the residue was treated with water and extracted into EtOAc. The organics were dried (MgSO i) and concentrated in vacuo to give an oily solid. The residue was dissolved in methanol and loaded onto a 70 g SCX column which was washed with methanol (150 mL) before eluting the product with 7 N N in methanol : methanol (1 :4). The eluent was concentrated in vacuo and the residue was purified by flash chromatography (DCM to 5% methanol in DCM) to give the desired compound. [00338] NMR delta (ppm)(DMSO-d6): 8.51 (1 Eta, s, ArH), 8.16 (1 H, d, ArH), 8.07 (2 H, d, ArH, NH), 7.58 (1 H, dd, ArH), 7.35 (1 H, d, ArH), 6.83 (1 H, s, ArH), 3.96-3.72 (3 H, m, CH3), 3.72 (3 H, s, CH3), 2.71 (2 H, q, CH2), 1.17 (3 H, t, CH3). [00339] LCMS (1 Ocm ESCI Bicarb MeCN) tR 2.77 (min) m/z 311 (MH+).

Reference： [1]Patent: WO2013/117649,2013,A1 .Location in patent: Paragraph 00337-00339

25
[ 1449506-72-2 ]
[ 7205-46-1 ]
[ 1449506-73-3 ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; XPhos; In 1,4-dioxane; at 100.0℃; for 1.5h;Inert atmosphere;	To stirred degassed (N2) 1,4-dioxane (230 mL) was added tert-butyl 4-(4-amino-3- ethylphenyl)-5,6-dihydropyridine-l(2H)-carboxylate (8.25 g, 27.3 mmol), 6-chloro-l -methyl- 1H- imidazo[4,5-c]pyridine (4.15 g, 24.8 mmol), tris(dibenzylideneacetone)dipalladium(0) (1.25 g, 1.37 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (1.30 g, 2.73 mmol) and sodium tert- butoxide (3.94 g, 30 mmol). The reaction mixture was heated to 100C for 1.5 h, cooled to room temperature, filtered through Celite and washed through with DCM. The filtrate was washed with water, dried (MgSO i), filtered and concentrated in vacuo and the resulting residue was purified by column chromatography using silica gel and eluting with 0-3%> MeOH in DCM. The fractions containing product were combined and concentrated in vacuo to give the desired compound. NMR delta (ppm)(DMSO-d6): 8.48 (1 H, d, NH), 8.04 (1 H, s, ArH), 7.89 (1 H, s, ArH), 7.56-7.49 (1 H, m, ArH), 7.30 (1 H, d, ArH), 7.23 (1 H, dd, ArH), 6.74-6.71 (1 H, m, ArH), 6.10 (1 H, s, CH), 4.00 (2 H, s, CH), 3.73-3.63 (3 H, m, CH3), 3.58-3.52 (2 H, m, CH), 2.70-2.59 (2 H, m, CH), 2.53-2.46 (2 H, s, CH), 1.55-1.35 (9 H, m, CH3), 1.18-1.09 (3 H, m, CH3).
	With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; XPhos; In 1,4-dioxane; at 100.0℃; for 1.5h;Inert atmosphere;	To stirred degassed (N2) 1,4-dioxane (230 mL) was added tert-butyl 4-(4-amino-3- ethylphenyl)-5,6-dihydropyridine-l(2H)-carboxylate (8.25 g, 27.3 mmol), 6-chloro-l -methyl- 1H- imidazo[4,5-c]pyridine (4.15 g, 24.8 mmol), tris(dibenzylideneacetone)dipalladium(0) (1.25 g, 1.37 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (1.30 g, 2.73 mmol) and sodium tert- butoxide (3.94 g, 30 mmol). The reaction mixture was heated to 100C for 1.5 h, cooled to room temperature, filtered through Celite and washed through with DCM. The filtrate was washed with water, dried (MgSO i), filtered and concentrated in vacuo and the resulting residue was purified by column chromatography using silica gel and eluting with 0-3% MeOH in DCM. The fractions containing product were combined and concentrated in vacuo to give the desired compound. NMR delta (ppm)(DMSO-d6): 8.48 (1 H, d, NH), 8.04 (1 H, s, ArH), 7.89 (1 H, s, ArH), 7.56-7.49 (1 H, m, ArH), 7.30 (1 H, d, ArH), 7.23 (1 H, dd, ArH), 6.74-6.71 (1 H, m, ArH), 6.10 (1 H, s, CH), 4.00 (2 H, s, CH), 3.73-3.63 (3 H, m, CH3), 3.58-3.52 (2 H, m, CH), 2.70-2.59 (2 H, m, CH), 2.53-2.46 (2 H, s, CH), 1.55-1.35 (9 H, m, CH3), 1.18-1.09 (3 H, m, CH3).

Reference： [1]Patent: WO2013/117649,2013,A1 .Location in patent: Paragraph 00341
[2]Patent: WO2013/117645,2013,A1 .Location in patent: Paragraph 00323

26
[ 1449515-90-5 ]
[ 7205-46-1 ]
[ 1449514-96-8 ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; In 1,4-dioxane; at 100.0℃; for 24h;	A stirred mixture of 4-ethyl-6-(thiophen-2-yl)pyridin-3-amine (0.15 g, 0.71 mmol), 6-chloro- 1 -methyl- lH-imidazo[4,5-c]pyridine (0.12 g, 0.71 mmol), sodium tert-butoxide ( 175 mg), tris(dibenzylideneacetone)dipalladium(0) (23 mg) and 2,2'-bis(diphenylphosphino)-l,l'-binaphthyl (22 mg) was heated in 1,4-dioxane (5 mL) at 100C in a sealed tube for 1 d. The mixture was evaporated in vacuo and the residue was partitioned between DCM and water. The organic phase was separated and the aqueous phase extracted with DCM (x 3), the combined organic phases were dried (MgSO i) and evaporated in vacuo. The residue was purified by flash chromatography (7N NH3 in methanol in DCM, 0-10%) to give the desired compound
	With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; In 1,4-dioxane; at 100.0℃; for 24h;Sealed tube;	A stirred mixture of 4-ethyl-6-(thiophen-2-yl)pyridin-3-amine (0.15 g, 0.71 mmol), 6-chloro- 1 -methyl- lH-imidazo[4,5-c]pyridine (0.12 g, 0.71 mmol), sodium tert-butoxide ( 175 mg), tris(dibenzylideneacetone)dipalladium(0) (23 mg) and 2,2'-bis(diphenylphosphino)-l,l'-binaphthyl (22 mg) was heated in 1,4-dioxane (5 mL) at 100 C in a sealed tube for 1 d. The mixture was evaporated in vacuo and the residue was partitioned between DCM and water. The organic phase was separated and the aqueous phase extracted with DCM (x 3), the combined organic phases were dried (MgSO^ and evaporated in vacuo. The residue was purified by flash chromatography (7N NH3 solution in MeOH in DCM, 0-10%) to give the desired compound.

Reference： [1]Patent: WO2013/117649,2013,A1 .Location in patent: Paragraph 00344
[2]Patent: WO2013/117645,2013,A1 .Location in patent: Paragraph 00552

27
[ 7205-46-1 ]
2-ethyl-4-fluoroaniline [ No CAS ]
[ 1449664-40-7 ]

Reference： [1]Patent: WO2013/117645,2013,A1

28
[ 64-18-6 ]
[ 87034-76-2 ]
[ 149-73-5 ]
[ 7205-46-1 ]

Yield	Reaction Conditions	Operation in experiment
	at 100.0℃; for 4h;	To a stirred solution of 6-Chloro-N-methyl-pyridine-3, 4-diamine (22 mmol) in trimethyl orthoformate (25 mL) was added formic acid (1 mL) and was heated at 100C for nearly 4 h when TLC showed the completion of reaction. The reaction was allowed to cool to room temperature and water (50 mL) was added and the mixture was extracted with ethyl acetate (4x50 mL), the combined organic layers were washed with aq. NaHCC>3 solution, dried over anhydrous sodium sulphate and concentration under reduced pressure gave the desired product Intermediate 2. H-NMR (400 MHz, DMSO-i: delta 3.84 (s, 3H), 7.83 (s, 1H), 8.39 (s, 1H), 8.74 (s, 1H). Mass (M+l): m/z 168.

Reference： [1]Patent: WO2013/117645,2013,A1 .Location in patent: Paragraph 00314

29
[ 932-32-1 ]
[ 7205-46-1 ]
[ 1449664-52-1 ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; XPhos; In 1,4-dioxane; at 100℃; for 2h;Sealed tube;	6-Chloro-l-methyl-lH-imidazo[4,5-c]pyridine (200 mg, 1.19 mmol), 2-chloro-N- methylaniline (185 mg, 1.31 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (57 mg, 0.12 mmol) and sodium tert-butoxide (172 mg, 1.79 mmol) were stirred in 1,4-dioxane (5 mL) and N2(g) was bubbled through the mixture for 10 min. Tris(dibenzylideneacetone)dipalladium(0) (54 mg, 0.06 mmol) was added and the dark mixture heated in a sealed tube at 100C for 2 h. The reaction mixture was cooled to room temperature and DCM and water were added. The aqueous phase was extracted with DCM and the combined organics filtered through a hydrophobic frit and then concentrated in vacuo. The residue was dissolved in DCM (5 mL) and passed through a PL-Thiol MP SPE+ column. DCM was passed through the column and the filtrate concentrated in vacuo. The residue was purified by preparative HPLC to give the desired compound. NuMuRhonu delta (ppm)(DMSO-d6): 8.47 (1 H, s, ArH), 8.02 (1 H, s, ArH), 7.59 (1 H, d, ArH), 7.47-7.38 (2 H, m, ArH), 7.39-7.31 (1 H, m, ArH), 6.39 (1 H, s, ArH), 3.66 (3 H, s, CH3), 3.35 (3 H, s , CH3). LCMS (lOcm ESCI Bicarb MeCN) Rt 3.22 (min) m/z 273 (MH+).

Reference： [1]Patent: WO2013/117645,2013,A1 .Location in patent: Paragraph 00419

30
[ 153304-75-7 ]
[ 7205-46-1 ]
[ 1449669-05-9 ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; XPhos; In 1,4-dioxane; at 85.0℃; for 4h;	Methyl 4-amino-3-ethylbenzoate (0.9 g, 5.02 mmol), 6-chloro-l-methyl-lH-imidazo[4,5- c]pyridine (0.802 g, 4.788 mmol) and sodium tert-butoxide (0.689 g, 7.18 mmol) were suspended in 1,4- dioxane (40 mL). The reaction was stirred under an atmosphere of N2 (g) for 20 min then tris(dibenzylideneacetone)dipalladium(0) (219 mg, 0.23 mmol) and 2-dicyclohexylphosphino-2',4',6'- triisopropylbiphenyl (228 mg, 0.478 mmol) were added. The reaction was heated to 85C for 4 h then concentrated in vacuo. The crude material was dissolved in MeOH (40 mL) and HC1 (4 mL, 4 M in dioxane) and the reaction was refluxed for 4 h to re-esterify the hydrolysed ester. The reaction was concentrated in vacuo, diluted with EtOAc and washed with water then brine. The organic layer was dried (MgSO i), filtered and concentrated in vacuo. The residue was purified by column chromatography using silica gel and eluting with DCM:MeOH 97:3 to give the desired compound

Reference： [1]Patent: WO2013/117645,2013,A1 .Location in patent: Paragraph 00424

31
[ 1369892-98-7 ]
[ 7205-46-1 ]
[ 1449664-59-8 ]

Reference： [1]Patent: WO2013/117645,2013,A1

32
[ 1449669-06-0 ]
[ 7205-46-1 ]
[ 1449515-72-3 ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; XPhos; In 1,4-dioxane; at 100.0℃; for 24h;Inert atmosphere;	To stirred degassed (N2) 1,4-dioxane (10 mL) was added 2-ethyl-4-(l-methyl-lH-pyrazol-4- yl)aniline (400 mg, 2.00 mmol), 6-chloro-l-methyl-lH-imidazo[4,5-c]pyridine (303 mg, 1.8 mmol), tris(dibenzylideneacetone)dipalladium(0) (82 mg, 0.09 mmol), 2-dicyclohexylphosphino-2',4',6'- triisopropylbiphenyl (86 mg, 0.18 mmol) and sodium tert-butoxide (260 mg, 2.7 mmol). The reaction mixture was heated to 100C for 1 d, cooled to room temperature, filtered through Celite and washed through with DCM. The reaction mixture was washed with water and the layers were separated and the aqueous layer further extracted with DCM. The organics were combined, dried (hydrophobic filter) and concentrated in vacuo and the resulting residue was purified by column chromatography using silica gel and eluting with 0-5% MeOH in DCM. The fractions containing product were combined and concentrated in vacuo to give the desired compound. NMR delta (ppm)(DMSO-d6): 8.47 (1 H, s, NH), 8.07 (1 H, s, ArH), 8.02 (1 H, s, ArH), 7.89-7.76 (2 H, m, ArH), 7.48-7.40 (2 H, m, ArH), 7.37-7.33 (1 H, m, ArH), 6.64 (1 H, s, ArH), 3.87 (3 H, s, CH3), 3.67 (3 H, s, CH3), 2.70-2.60 (2 H, m, CH2), 1.20-1.11 (3 H, m, CH3). LCMS (lOcm ESCI Bicarb MeCN) Rt 2.67 (min) m/z 333 (MH+).

Reference： [1]Patent: WO2013/117645,2013,A1 .Location in patent: Paragraph 00435

33
[ 1449669-06-0 ]
[ 7205-46-1 ]
[ 1449664-60-1 ]

Reference： [1]Patent: WO2013/117645,2013,A1

34
[ 1449516-29-3 ]
[ 7205-46-1 ]
[ 1449515-73-4 ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; XPhos; In 1,4-dioxane; at 100.0℃; for 24h;Inert atmosphere;	General procedure: To stirred degassed (N2) 1,4-dioxane (10 mL) is added the product of step i) above (2.00 mmol), 6-chloro-l -methyl- lH-imidazo[4,5-c]p y r i d i n e ( 3 0 3 m g , 1 . 8 m m o l ) , tris(dibenzylideneacetone)dipalladium(0) (82 mg, 0.09 mmol), 2-dicyclohexylphosphino-2',4',6'- triisopropylbiphenyl (86 mg, 0.18 mmol) and sodium tert-butoxide (260 mg, 2.7 mmol). The reaction mixture is heated to 100C for 1 d, cooled to room temperature, filtered through Celite and washed through with DCM. The reaction mixture is washed with water and the layers are separated and the aqueous layer further extracted with DCM. The organics are combined, dried (hydrophobic filter) and concentrated in vacuo and the resulting residue is purified by column chromatography using silica gel. The fractions containing product are combined and concentrated in vacuo to give the desired compound

Reference： [1]Patent: WO2013/117645,2013,A1 .Location in patent: Paragraph 00347; 00834

35
[ 1449516-29-3 ]
[ 7205-46-1 ]
[ 1449667-47-3 ]

Reference： [1]Patent: WO2013/117645,2013,A1

36
[ 1449669-12-8 ]
[ 7205-46-1 ]
[ 1449664-73-6 ]

Yield	Reaction Conditions	Operation in experiment
	With chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl][2-(2-aminoethyl)phenyl]palladium(II); sodium t-butanolate; XPhos; In 1,4-dioxane; at 100.0℃; for 8h;	At room temperature, 6-chloro-l -methyl- lH-imidazo[4,5-c]pyri dine (0.135 g, 0.80 mmol) was stirred with 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.017 g, 0.0365 mmol), chloro(2-dicyclohexylphosphino-2',4',6'-triisopropyl-l, -biphenyl)[2-(2- aminoethyl)phenyl)]palladium(II) (0.027 g, 0.0365 mmol), sodium tert-butoxide (0.105 g, 1.10 mmol) and 2-ethyl-N-methyl-4-(thiazol-5-yl)aniline (0.160 g, 0.73 mmol) in 1 ,4-dioxane (5 mL) and degassed under N2 (g) for 10 min. At this point the reaction was stirred at 100C for 8 h. The mixture was cooled to room temperature and filtered through Celite and concentrated in vacuo. The resulting residue was dissolved in DMSO (1 mL) and purified by preparative HPLC to give the desired compound. NMR delta (ppm)(DMSO-d6): 9.09 (1 H, d, ArH), 8.47 (1 H, d, ArH), 8.35-8.33 (1 H, m, ArH), 7.98 (1 H, s, ArH), 7.67 (1 H, d, ArH), 7.60 (1 H, dd, ArH), 7.24 (1 H, d, ArH), 6.26 (1 H, d, ArH), 3.61 (3 H, s, CH3), 2.48-2.42 (2 H, m, CH2), 1.12 (3 H, t, CH3), (CH3 under water peak). LCMS (10cm_ESCI_Formic_MeCN) Rt 2.42 (min) m/z 350 (MH+).

Reference： [1]Patent: WO2013/117645,2013,A1 .Location in patent: Paragraph 00461

37
[ 1449669-00-4 ]
[ 7205-46-1 ]
[ 1449669-01-5 ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate; In 1,4-dioxane; at 105.0℃; for 1.5h;Inert atmosphere;	General procedure: A solution of 2-ethyl-4-(l-(4-methoxybenzyl)-lH-pyrazol-4-yl)aniline (0.013 M), 6-chloro- 1 -methyl- lH-imidazo[4,5-c]pyridine (0.013 M), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (10 mol%) and sodium tert-butoxide (0.0195 M) in dry 1,4-dioxane (100 mL) is stirred under N2 for 15 min. Tris(dibenzylideneacetone)dipalladium(0) (5 mol%) is added and the reaction is stirred at 105C for 1.5 h. The mixture is concentrated in vacuo and the residue is dissolved in DCM and filtered through Celite. The filtrate is washed with water, dried MgS04 and concentrated in vacuo. The residue is purified by silica gel flash chromatography (1 - 5% MeOH in DCM) to give the desired compound

Reference： [1]Patent: WO2013/117645,2013,A1 .Location in patent: Paragraph 00384

38
[ 1449669-16-2 ]
[ 7205-46-1 ]
[ 1449514-97-9 ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; XPhos; In 1,4-dioxane; water; at 100.0℃; for 1h;Inert atmosphere;	To stirred degassed (N2) 1,4-dioxane (5 mL) was added 4-methoxy-6-(thiophen-2-yl)pyridin- 3-amine (140 mg, 0.67 mmol), 6-chloro-l -methyl-lH-imidazo[4,5-c]pyridine (100 mg, 0.6 mmol), tris(dibenzylideneacetone)dipalladium(0) (28 mg, 0.03 mmol), 2-dicyclohexylphosphino-2',4',6'- triisopropylbiphenyl (29 mg, 0.09 mmol) and sodium tert-butoxide (86 mg, 0.9 mmol). The reaction mixture was heated to 100C for 1 d, cooled to room temperature, filtered through Celite and washed through with DSM. The reaction mixture was washed with water and the layers were separated, the aqueous layer was further extracted with DCM. The organics were combined, dried (hydrophobic filter) and concentrated in vacuo and the resulting residue was purified by column chromatography using silica and eluting with MeOH in EtOAc (0-10%) to give the desired compound

Reference： [1]Patent: WO2013/117645,2013,A1 .Location in patent: Paragraph 00507

39
[ 1449669-16-2 ]
[ 7205-46-1 ]
[ 1449665-04-6 ]

Reference： [1]Patent: WO2013/117645,2013,A1

40
[ 1449668-93-2 ]
[ 7205-46-1 ]
[ 1449668-94-3 ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 110.0℃; for 16h;Inert atmosphere;	General procedure: The corresponding amine (0.58 mmol) is added to a solution of intermediate 2 (0.45 mmol) and cesium carbonate (0.62 mmol) in Dioxane (3 mL). Degassing is done for 5 min, followed by addition of a solution previously sonicated for 10 min of Xantphos (0.06 equiv), Pd2(dba)3 (0.03 equiv) in dioxane (1 mL) under nitrogen. The reaction is heated at 110C for 16 h. After completion, water and DCM are added and this mixture is filtered through a phase separator. The organic layers are concentrated under reduced pressure. The crude product is purified by preparative HPLC to afford desired compound.

Reference： [1]Patent: WO2013/117645,2013,A1 .Location in patent: Paragraph 00330; 00335

41
[ 114747-31-8 ]
[ 7205-46-1 ]
[ 1449669-17-3 ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In 1,4-dioxane;Inert atmosphere; Reflux;	2-Ethyl-4-methoxy-phenylamine (63 mg, 0.42 mmol, 1.0 equiv), 6-Chloro-l -methyl- 1H- imidazo[4,5-c]-pyridine (77 mg, 0.46 mmol, 1.1 equiv), CS2CO3 (411 mg, 1.26 mmol, 3.0 equiv), BetaGammaNuAlphaRho (26 mg, 0.04 mmol, 0.1 equiv) and Pd2(dba)3 (19 mg, 0.02 mmol, 0.05 equiv) were dissolved in dry dioxane (5 mL) under N2 atmosphere. The mixture was sonicated for 5 mn under N2 flow and then refluxed until full conversion was observed by LCMS. It was then cooled down and concentrated to dryness, diluted in DCM and washed with water (3x 20 mL). The aqueous layer was extracted with DCM (3x 30 mL) and the combined organic layer was dried over Na2SO (, filtered and concentrated to dryness. Purification was performed by column chromatography using the following eluant: EtO Ac (20 CV), MeOH/EtOAc (1 :19) (10 CV), MeOH/EtOAc (1 :9) (10 CV) to afford the desired compound.

Reference： [1]Patent: WO2013/117645,2013,A1 .Location in patent: Paragraph 00518

42
[ 114747-31-8 ]
[ 7205-46-1 ]
[ 1449665-09-1 ]

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43
[ 7205-46-1 ]
(4-methoxybenzyl)zinc(II) chloride [ No CAS ]
[ 1449665-13-7 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; at 70.0℃; for 12h;	(4-methoxybenzyl)zinc(II) chloride in solution in THF (0.45 mmol) was added to a solution of intermediate 1 (0.29 mmol) and Pd(PPh3)4 (0.09 mmol) in THF (1 mL) . The reaction heated at 70C for 12 h. After completion, water and DCM were added and this mixture was filtered through a phase separator. The organic layers were concentrated under reduced pressure. The crude product was purified by preparative HPLC to give the desired compound. [00530] Analytical: Waters Acquity UPLC BEH CI 8 1.7muetaiota, 2.1mm ID x 50mm L (Part No.186002350).

Reference： [1]Patent: WO2013/117645,2013,A1 .Location in patent: Paragraph 00529; 00530

44
[ 1449669-23-1 ]
[ 7205-46-1 ]
[ 1449669-24-2 ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In 1,4-dioxane; at 110.0℃; for 20h;Inert atmosphere; Sealed tube;	6-Chloro-l-methyl-lH-imidazo[4,5-c]pyridine (0.38 g, 2.29 mmol), tert-butyl 3-(4-amino-3- fluorophenyl)azetidine-l-carboxylate (0.67 g, 2.51 mmol), cesium carbonate (2.23 g, 6.86 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.052 g, 0.057 mmol) and 2,2'-bis(diphenylphosphino)-l,l'- binaphthyl (0.071, 0.11 mmol) were heated in 1,4-dioxane at 110 C under nitrogen in a sealed tube for 20 h. The mixture was evaporated in vacuo and the residue was partitioned between DCM and water. The organic phase was separated and the aqueous phase extracted with DCM (x 3), the combined organic phases were dried (MgSO i) and evaporated in vacuo. The residue was purified by flash chromatography (5% EtOAc in isohexane to 100% EtOAc and then with 10% MeOH in DCM) to give the desired compound.

Reference： [1]Patent: WO2013/117645,2013,A1 .Location in patent: Paragraph 00537

45
[ 1449669-29-7 ]
[ 7205-46-1 ]
[ 1449669-30-0 ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; XPhos; In 1,4-dioxane; for 3.5h;Inert atmosphere; Reflux;	A stirred mixture of 4-ethyl-6-(l-methyl-lH-pyrazol-4-yl)pyridin-3-amine (36 mg, 0.17 mmol), 6-chloro-l -methyl- lH-imidazo[4,5-c]pyridine (30 mg, 0.18 mmol), 2-dicyclohexylphosphino- 2',4',6'-triisopropylbiphenyl (12 mg) and sodium tert-butoxide (30 mg, 0.3 mmol) in 1,4-dioxane (7 mL) was degassed (N2). Tris(dibenzylideneacetone)dipalladium(0) (10 mg) was added and the mixture was refluxed for 3.5 h. The mixture was evaporated in vacuo and the residue was purified by flash chromatography (DCM to 20% 7N NH3 in MeOH in DCM) to give the desired compound.

Reference： [1]Patent: WO2013/117645,2013,A1 .Location in patent: Paragraph 00547

46
[ 1449669-29-7 ]
[ 7205-46-1 ]
[ 1449665-20-6 ]

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47
[ 1449515-90-5 ]
[ 7205-46-1 ]
[ 1449665-22-8 ]

Reference： [1]Patent: WO2013/117645,2013,A1

48
[ 61638-00-4 ]
[ 7205-46-1 ]
[ 1449669-32-2 ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In 1,4-dioxane; for 20h;Inert atmosphere; Reflux;	4-Amino-3-ethyl-phenol (100 mg, 0.73 mmol, 1.0 equiv), 6-Chloro-l -methyl- 1H- imidazo[4,5-c]-pyridine (134 mg, 0.80 mmol, 1.1 equiv), Cs2C03 (714 mg, 2.19 mmol, 3.0 equiv), BetaGammaNuAlphaRho (46 mg, 0.07 mmol, 0.1 equiv), and Pd2(dba)3 (33 mg, 0.04 mmol, 0.05 equiv) were dissolved in dry dioxane (5 mL) under N2 atmosphere. The mixture was sonicated for 5 mn under N2 flow and then re fluxed for 20h. Full conversion was observed by LCMS. It was then cooled down and concentrated to dryness, diluted in DCM and washed with water (3x 20 mL). The aqueous layer was extracted with DCM (3x 30 mL) and the combined organic layer was dried over Na2SO i, filtered and concentrated to dryness. Purification was performed by column chromatography using the following eluant: EtOAc/Petroleum Ether (1 : 1) to EtOAc (over 5 CV), MeOH/EtOAc (1 : 19) (10 CV), MeOH/EtOAc (1 :9) (10 CV) to afford the desired compound

Reference： [1]Patent: WO2013/117645,2013,A1 .Location in patent: Paragraph 00557

49
[ 1449669-37-7 ]
[ 7205-46-1 ]
[ 1449669-38-8 ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; In 1,4-dioxane; at 20.0℃; for 16h;Inert atmosphere;	A mixture of the aniline (1 equiv, 40 mg), 6-chloro-l-methyl-lH-imidazo[4,5-c]pyridine (1.1 equiv, 32 mg), BINAP (0.2 equiv, 44 mg), Cs2C03 (3 equiv, 325 mg) and tris(dibenzylideneacetone)dipalladium(0) (0.1 equiv, 24 mg) in dry 1,4-dioxane (10 mL), degassed under (N2), was heated at reflux temperature for 16 h. The solution was concentrated in vacuo and purified by silica chromatography to give the desired product. LC-MS: [M+H]+ 361.0

Reference： [1]Patent: WO2013/117645,2013,A1 .Location in patent: Paragraph 00573

50
[ 1449669-37-7 ]
[ 7205-46-1 ]
[ 1449665-29-5 ]

Reference： [1]Patent: WO2013/117645,2013,A1

51
[ 7205-46-1 ]
[ 63837-12-7 ]
[ 1449515-40-5 ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In 1,4-dioxane; for 15h;Reflux;	General procedure: To a solution of intermediate 2 (14.9 mmol) in dioxane (100 mL) is added the corresponding aniline (22.4 mmol), cesium carbonate (22.4 mmol), BetaGammaNuAlphaRho (0.9 mmol) a n d tris(dibenzylideneacetone)dipalladium (0.45 mmol). The reaction mixture is refluxed for 15 h, filtered on Celite, evaporated to dryness and purified on silica gel to give the desired compound

Reference： [1]Patent: WO2013/117645,2013,A1 .Location in patent: Paragraph 00336; 00834

52
[ 7205-46-1 ]
[ 1449664-44-1 ]

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53
[ 7205-46-1 ]
[ 1449664-45-2 ]

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54
[ 7205-46-1 ]
[ 1449664-46-3 ]

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55
[ 7205-46-1 ]
[ 1449664-47-4 ]

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56
[ 7205-46-1 ]
[ 1449667-04-2 ]

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57
[ 7205-46-1 ]
[ 1449664-48-5 ]

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58
[ 7205-46-1 ]
[ 1449669-04-8 ]

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59
[ 7205-46-1 ]
[ 1449664-53-2 ]

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60
[ 7205-46-1 ]
[ 1449664-54-3 ]

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61
[ 7205-46-1 ]
[ 1449664-55-4 ]

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62
[ 7205-46-1 ]
[ 1449664-56-5 ]

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63
[ 7205-46-1 ]
[ 1449664-57-6 ]

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[ 7205-46-1 ]
[ 1449664-58-7 ]

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[ 7205-46-1 ]
[ 1449667-42-8 ]

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[ 7205-46-1 ]
[ 1449667-53-1 ]

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[ 7205-46-1 ]
[ 1449669-07-1 ]

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68
[ 7205-46-1 ]
[ 1449664-61-2 ]

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69
[ 7205-46-1 ]
[ 1449664-62-3 ]

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[ 7205-46-1 ]
[ 1449664-63-4 ]

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[ 7205-46-1 ]
[ 1449664-64-5 ]

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[ 7205-46-1 ]
[ 1449667-59-7 ]

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73
[ 7205-46-1 ]
[ 1449667-60-0 ]

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74
[ 7205-46-1 ]
[ 1449670-50-1 ]

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[ 7205-46-1 ]
[ 1449664-66-7 ]

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[ 7205-46-1 ]
[ 1449664-68-9 ]

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[ 7205-46-1 ]
[ 1449667-73-5 ]

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[ 7205-46-1 ]
[ 1449667-77-9 ]

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79
[ 7205-46-1 ]
[ 1449664-71-4 ]

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80
[ 7205-46-1 ]
[ 1449667-95-1 ]

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81
[ 7205-46-1 ]
[ 1449664-75-8 ]

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[ 7205-46-1 ]
[ 1449664-94-1 ]

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83
[ 7205-46-1 ]
[ 1449664-76-9 ]

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84
[ 7205-46-1 ]
[ 1449506-74-4 ]

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[ 7205-46-1 ]
[ 1449664-78-1 ]

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86
[ 7205-46-1 ]
[ 1449664-81-6 ]

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87
[ 7205-46-1 ]
[ 1449668-09-0 ]

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[ 7205-46-1 ]
[ 1449664-86-1 ]

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6-Chloro-1H-imidazo[4,5-c]pyridine

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[ 52559-17-8 ]

6-Chloro-3H-imidazo[4,5-c]pyridin-4-amine

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[ 50432-68-3 ]

4-Chloro-1-methyl-1H-imidazo[4,5-c]pyridine

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[ 887147-19-5 ]

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Related Parent Nucleus of
[ 7205-46-1 ]

Other Aromatic Heterocycles

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6-Chloro-1H-imidazo[4,5-c]pyridine

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

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

[ CAS No. 7205-46-1 ] {[proInfo.proName]}

Quality Control of [ 7205-46-1 ]

Related Doc. of [ 7205-46-1 ]

Product Details of [ 7205-46-1 ]

Calculated chemistry of [ 7205-46-1 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 7205-46-1 ]

Application In Synthesis of [ 7205-46-1 ]

[ 7205-46-1 ] Synthesis Path-Upstream 1~8

[ 7205-46-1 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 7205-46-1 ]

Chlorides

Related Parent Nucleus of [ 7205-46-1 ]

Other Aromatic Heterocycles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 7205-46-1 ]

Related Parent Nucleus of
[ 7205-46-1 ]