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[ CAS No. 1206641-31-7 ] {[proInfo.proName]}

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Chemical Structure| 1206641-31-7

Chemical Structure| 1206641-31-7

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Quality Control of [ 1206641-31-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1206641-31-7 ]

Product Details of [ 1206641-31-7 ]

CAS No. :	1206641-31-7	MDL No. :	MFCD18383917
Formula :	C₁₆H₂₀BNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LQTZQARAJYGKBH-UHFFFAOYSA-N
M.W :	269.15	Pubchem ID :	53423523
Synonyms :

Calculated chemistry of [ 1206641-31-7 ]

Physicochemical Properties

Num. heavy atoms :	20
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.56
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	79.82
TPSA :	42.25 Å²

Pharmacokinetics

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

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	2.91
Log Po/w (WLOGP) :	2.48
Log Po/w (MLOGP) :	1.81
Log Po/w (SILICOS-IT) :	2.82
Consensus Log Po/w :	2.0

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.43
Solubility :	0.0995 mg/ml ; 0.00037 mol/l
Class :	Soluble
Log S (Ali) :	-3.46
Solubility :	0.0937 mg/ml ; 0.000348 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.9
Solubility :	0.00337 mg/ml ; 0.0000125 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.87

Safety of [ 1206641-31-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1206641-31-7 ]

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

Downstream synthetic route of [ 1206641-31-7 ]

[ 1206641-31-7 ] Synthesis Path-Downstream 1~45

2
[ 1206641-31-7 ]
[ 22931-71-1 ]
ethyl 4-(4-(1-cyanocyclopropyl)phenyl)-6-methoxyquinoline-3-carboxylate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 4883 - 4903

3
[ 1206641-31-7 ]
[ 77156-85-5 ]
C₂₃H₂₀N₂O₃ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 4883 - 4903

4
[ 1206641-31-7 ]
[ 21168-41-2 ]
C₂₂H₁₇ClN₂O₂ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 4883 - 4903

5
[ 318685-01-7 ]
[ 1206641-31-7 ]
C₂₂H₁₆F₂N₂O₂ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 4883 - 4903

6
[ 1206641-31-7 ]
[ 150258-20-1 ]
C₂₂H₁₆F₂N₂O₂ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 4883 - 4903

7
[ 1206641-31-7 ]
ethyl 4-bromo-6-fluoroquinoline-3-carboxylate [ No CAS ]
ethyl 4-(4-(1-cyanocyclopropyl)phenyl)-6-fluoroquinoline-3-carboxylate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 4883 - 4903

8
[ 1206641-31-7 ]
1-(4-(3-(4-(cyclopropanecarbonyl)piperazine-1-carbonyl)-6-fluoroquinolin-4-yl)phenyl)cyclopropanecarbonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 4883 - 4903

9
[ 1206641-31-7 ]
1-(4-(6-fluoro-3-(4-(methylsulfonyl)piperazine-1-carbonyl)quinolin-4-yl)phenyl)cyclopropanecarbonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 4883 - 4903

10
[ 1206641-31-7 ]
4-(4-(4-(1-cyanocyclopropyl)phenyl)-6-fluoroquinoline-3-carbonyl)-N,N-dimethylpiperazine-1-sulfonamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 4883 - 4903

11
[ 1206641-31-7 ]
4-(4-(4-(1-cyanocyclopropyl)phenyl)-6-fluoroquinoline-3-carbonyl)-N,N-dimethylpiperazine-1-carboxamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 4883 - 4903

12
[ 1206641-31-7 ]
1-(4-(6-chloro-3-(4-(methylsulfonyl)piperazine-1-carbonyl)quinolin-4-yl)phenyl)cyclopropanecarbonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 4883 - 4903

13
[ 1206641-31-7 ]
1-(4-(6-chloro-3-(4-(cyclopropanecarbonyl)piperazine-1-carbonyl)quinolin-4-yl)phenyl)cyclopropanecarbonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 4883 - 4903

14
[ 1206641-31-7 ]
1-(4-(6-methoxy-3-(4-(methylsulfonyl)piperazine-1-carbonyl)quinolin-4-yl)phenyl)cyclopropane-1-carbonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 4883 - 4903

15
[ 1206641-31-7 ]
1-(4-(7-methoxy-3-(4-(methylsulfonyl)piperazine-1-carbonyl)quinolin-4-yl)phenyl)cyclopropane-1-carbonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 4883 - 4903

16
[ 1206641-31-7 ]
1-(4-(6,7-difluoro-3-(4-(methylsulfonyl)piperazine-1-carbonyl)quinolin-4-yl)phenyl)cyclopropane-1-carbonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 4883 - 4903

17
[ 1206641-31-7 ]
1-(4-(6,8-difluoro-3-(4-(methylsulfonyl)piperazine-1-carbonyl)quinolin-4-yl)phenyl)cyclopropane-1-carbonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 4883 - 4903

18
[ 1206641-31-7 ]
1-(4-(6-methoxy-3-(4-(methylsulfonyl)piperazine-1-carbonyl)quinolin-4-yl)phenyl)cyclopropane-1-carbonitrile hydrochloride [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 4883 - 4903

19
[ 1206641-31-7 ]
1-(4-(7-methoxy-3-(4-(methylsulfonyl)piperazine-1-carbonyl)quinolin-4-yl)phenyl)cyclopropane-1-carbonitrile hydrochloride [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 4883 - 4903

20
[ 1206641-31-7 ]
1-(4-(6,7-difluoro-3-(4-(methylsulfonyl)piperazine-1-carbonyl)quinolin-4-yl)phenyl)cyclopropane-1-carbonitrile hydrochloride [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 4883 - 4903

21
[ 1206641-31-7 ]
1-(4-(6,8-difluoro-3-(4-(methylsulfonyl)piperazine-1-carbonyl)quinolin-4-yl)phenyl)cyclopropane-1-carbonitrile hydrochloride [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 4883 - 4903

22
[ 1206641-31-7 ]
1-(4-(3-(4-(cyclopropanecarbonyl)piperazine-1-carbonyl)-6-fluoroquinolin-4-yl)phenyl)cyclopropanecarbonitrile trifluoroacetate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 4883 - 4903

23
[ 1206641-31-7 ]
1-(4-(6-fluoro-3-(4-(methylsulfonyl)piperazine-1-carbonyl)quinolin-4-yl)phenyl)cyclopropanecarbonitrile trifluoroacetate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 4883 - 4903

24
[ 1206641-31-7 ]
4-(4-(4-(1-cyanocyclopropyl)phenyl)-6-fluoroquinoline-3-carbonyl)-N,N-dimethylpiperazine-1-sulfonamide trifluoroacetate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 4883 - 4903

25
[ 1206641-31-7 ]
4-(4-(4-(1-cyanocyclopropyl)phenyl)-6-fluoroquinoline-3-carbonyl)-N,N-dimethylpiperazine-1-carboxamide trifluoroacetate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 4883 - 4903

26
[ 1206641-31-7 ]
1-(4-(6-chloro-3-(4-(methylsulfonyl)piperazine-1-carbonyl)quinolin-4-yl)phenyl)cyclopropanecarbonitrile trifluoroacetate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 4883 - 4903

27
[ 1206641-31-7 ]
1-(4-(6-chloro-3-(4-(cyclopropanecarbonyl)piperazine-1-carbonyl)quinolin-4-yl)phenyl)cyclopropanecarbonitrile trifluoroacetate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 4883 - 4903

28
[ 1206641-31-7 ]
4-(4-(1-cyanocyclopropyl)phenyl)-6-fluoroquinoline-3-carboxylic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 4883 - 4903

29
[ 1206641-31-7 ]
4-(4-(1-cyanocyclopropyl)phenyl)-6-methoxyquinoline-3-carboxylic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 4883 - 4903

30
[ 1206641-31-7 ]
6-chloro-4-(4-(1-cyanocyclopropyl)phenyl)quinoline-3-carboxylic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 4883 - 4903

31
[ 1206641-31-7 ]
4-(4-(1-cyanocyclopropyl)phenyl)-7-methoxyquinoline-3-carboxylic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 4883 - 4903

32
[ 1206641-31-7 ]
4-(4-(1-cyanocyclopropyl)phenyl)-6,7-difluoroquinoline-3-carboxylic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 4883 - 4903

33
[ 1206641-31-7 ]
4-(4-(1-cyanocyclopropyl)phenyl)-6,8-difluoroquinoline-3-carboxylic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 4883 - 4903

34
[ 1206641-31-7 ]
[ 29274-24-6 ]
C₁₆H₁₂N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
600 mg	With potassium phosphate; bis[tris( 1,1-dimethylethyl)phosphine]-palladium; In 1,4-dioxane; water; at 80.0℃; for 16.0h;	A mixture of A-7 (300.0 mg, 1.95 mmol), 1-[4-(4,4,5,5-tetramethyl-1,3 ,2-dioxaborolan-2-yl)phenyllcyclopropanecarbonitrile (629.81 mg, 2.34 mmol), Pd(t-Bu3P)2(149.48 mg, 292.50 pmol) and K3P04 (827.85 mg, 3.90 mmol) in dioxane (10 mL) and H20(3.90 mL) was stirred at 80 C for 16 hours. The mixture was concentrated to give the crudeproduct, which was purified by silica gel (EtOAc in PE = 10% to 20% to 100%) to afford A-il(600.00 mg, 1.86 mmol) as a solid. ?H NMR (400MHz, DMSO-d6) 0119.19 (dd, 1H), 8.30 - 8.17(m, 3H), 7.66 (d, 1H), 7.49 (dd, 2H), 6.76 (d, 1H), 1.91 - 1.80 (m, 2H), 1.68 - 1.58 (m, 2H).LCMS R = 0.762 mm in 1.5 mins chromatography, MS ESI calcd. for C,6H,3N4 [M+H1 261.1, found 260.9.

Reference： [1]Patent: WO2018/98500,2018,A1 .Location in patent: Page/Page column 87

35
[ 1206641-31-7 ]
[ 76537-23-0 ]
1-(4-imidazo[1,2-a]pyrazin-6-ylphenyl)cyclopropanecarbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With potassium phosphate; bis[tris( 1,1-dimethylethyl)phosphine]-palladium; In 1,4-dioxane; water; at 80.0℃; for 16.0h;	To a solution of 6-chloroimidazo[1,2-alpyrazine (200 mg, 1.3 mmol) in 1,4-dioxane (4 mL) and water (0.40 mL) was added 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl)phenyllcyclopropanecarbonitrile (420.63 mg, 1.56 mmol), Pd(t-Bu3P)2 (99.84 mg, 0.20mmol) and K3P04 (552.97 mg, 2.6 mmol). The resulting mixture was stirred at 80 C under N2 for 16 hours to give a suspension. The reaction mixture was cooled to room temperature and filtered through Celite. The filtrate was concentrated to give the crude product. The crude product was purified by silica gel column with EtOAc in PE (10% to 30% to 50% to 80%) to give 1 -(4-imidazo[ 1 ,2-alpyrazin-6-ylphenyl)cyclopropanecarbonitrile (240 mg, 71% yield) as a solid. ?H NMR (400 MHz, CDC13) on 9.20 (s, 1H), 8.48 (s, 1H), 7.94 (d, 2H), 7.85 (s, 1H), 7.77 (s, 1H), 7.42 (d, 2H), 1.83 - 1.79 (m, 2H), 1.51 - 1.46 (m, 2H).

Reference： [1]Patent: WO2018/98500,2018,A1 .Location in patent: Page/Page column 115; 116

36
[ 1206641-31-7 ]
1-[4-(3-iodoimidazo[1,2-a]pyrazin-6-yl)phenyl]cyclopropanecarbonitrile [ No CAS ]

Reference： [1]Patent: WO2018/98500,2018,A1

37
[ 1206641-31-7 ]
1-[4-[3-(trifluoromethyl)imidazo[1,2-a]pyrazin-6-yl]phenyl]cyclopropanecarbonitrile [ No CAS ]

Reference： [1]Patent: WO2018/98500,2018,A1

38
[ 1060812-84-1 ]
[ 1206641-31-7 ]
1-(4-pyrazolo[1,5-a]pyridin-5-ylphenyl)cyclopropanecarbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With potassium phosphate; bis[tris( 1,1-dimethylethyl)phosphine]-palladium; In 1,4-dioxane; water; at 80℃; for 16.0h;	A mixture of 5-bromopyrazolo[1,5-alpyridine (0.15 g, 761.30 pmol), 1-[4-(4,4,5,5- tetramethyl- 1,3 ,2-dioxaborolan-2-yl)phenyllcyclopropanecarbonitrile (245.88 mg, 913.56 jimol), Pd(t-Bu3P)2 (58.36 mg, 114.19 pmol) and K3P04 (323.20 mg, 1.52 mmol) in dioxane (2 mL) and H20 (0.2 mL) was stirred at 80 °C for 16 hours. The crude product was cooled to r.t., dilutedwith H20 (10 mL), extracted with EtOAc (30 mL x 2). The combined organic phase was washed with brine (10 mL), dried over Na2504, filtered and concentrated to give the crude product. The crude product was purified by silica gel column (PE: EtOAc = 10:1 to 5:1 to 1:1) to give 1 -(4- pyrazolo[1,5-alpyridin-5-ylphenyl)cyclopropanecarbonitrile (150 mg, 76percent yield) as a solid. ?H NMR (400 MHz, CDC13) 011 8.53 (d, 1H), 7.99 (d, 1H), 7.72 (d, 1H), 7.64 (d, 2H), 7.41 (d, 2H),7.00 (dd, 1H), 6.58 (d, 1H), 1.83 - 1.78 (m, 2H), 1.50 - 1.46 (m, 2H).

Reference： [1]Patent: WO2018/98500,2018,A1 .Location in patent: Page/Page column 127; 128

39
[ 1206641-31-7 ]
C₈H₄ClF₃N₂ [ No CAS ]
C₁₈H₁₂F₃N₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
7.74 mg	With potassium phosphate; bis[tris( 1,1-dimethylethyl)phosphine]-palladium; In 1,4-dioxane; water; at 80.0℃; for 16.0h;	A mixture of A-4 (70.00 mg, 317.35 jimol), 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyllcyclopropanecarbonitrile (128.12 mg, 476.03 pmol), Pd(t-Bu3P)2(32.44 mg, 63.47 pmol) and K3P04 (134.73 mg, 634.70 pmol) in dioxane (5 mL) and H20 (1mL) was stirred at 80 C for 16 hours under N2. The mixture was then concentrated to give the crude product, which was purified by Prep-TLC (PE : EtOAc = 5: 1) and Prep-HPLC to afford Compound 5 (7.74 mg) as a solid. 1H NMR (400 MHz, CDCl3) oe11 8.35 (s, 1H), 8.00 (d, 1H),7.81 (d, 1H), 7.63 - 7.55 (m, 3H), 7.48 - 7.41 (m, 2H), 1.86 - 1.78 (m, 2H), 1.51 - 1.45 (m, 2H).LCMS R = 1.077 mm in 2.0 mm chromatography, MS ESI calcd. for C18H13F3N3 [M+H1328.1, found 327.9.

Reference： [1]Patent: WO2018/98500,2018,A1 .Location in patent: Page/Page column 83

40
[ 1206641-31-7 ]
C₈H₄ClF₃N₂ [ No CAS ]
C₁₈H₁₂F₃N₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
14.45 mg	With potassium phosphate; bis(tri-t-butylphosphine)palladium(0); In 1,4-dioxane; water; at 80.0℃; for 16.0h;	A mixture of A-3 (70.00 mg, 317.35 muiotaetaomicron), l-[4-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)phenyl]cyclopropanecarbonitrile (128.12 mg, 476.03 muiotaetaomicron), Pd(i-Bu3P)2 (24.33 mg, 47.60 muiotaetaomicron) and K3P04 (134.73 mg, 634.70 muiotaetaomicron) in H20 (600 mu) and dioxane (3 mL) was stirred at 80 C for 16 hours. The mixture was concentrated to give a residue which was purified by prep-HPLC (column: Kromasil (150 x 25 mm, 10 muiotaeta); A = H20 (0.05% NH4OH) and B = CH3CN; 50%-60% B over 8 minutes) to give Compound 4 (14.45 mg, 44.15 muiotaetaomicron) as a solid. 1H NMR (400MHz, CDC13) = 8.26 (s, 1H), 7.67 (dd, 1H), 7.60 - 7.55 (m, 3H), 7.44 (d, 2H), 7.20 (dd, 1H), 1.85 - 1.78 (m, 2H), 1.52 - 1.45 (m, 2H). LCMS R, = 1.19 min using Method A, MS ESI calcd. for Ci8H13F3N3 [M+H]+ 328.1, found 327.9.

Reference： [1]Patent: WO2018/98491,2018,A1 .Location in patent: Page/Page column 81

41
[ 1206641-31-7 ]
3-bromo-6-(trifluoromethyl)imidazo[1,5-a]pyrimidine [ No CAS ]
C₁₇H₁₁F₃N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
23.04 mg	With potassium phosphate; bis(tri-t-butylphosphine)palladium(0); In 1,4-dioxane; at 80.0℃; for 16.0h;	A mixture of l-[4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)phenyl]cyclopropanecarbonitrile (182.12 mg, 0.68 mmol), A-20 (90.00 mg, 0.34 mmol), Pd(i- Bu3P)2 (34.58 mg, 0.07 mmol) and K3P04 (143.63 mg, 0.68 mmol) in 1,4-dioxane (3 mL) and water (0.50 mL) was stirred at 80 C for 16 hours. After cooling to room temperature, the mixture was filtered through silica gel and eluted with EtOAc (20 mL x 2), concentrated, diluted with EtOAc (30 mL), washed with water (10 mL x 2) and brine (10 mL), dried over Na2S04, filtered and concentrated to give the crude product, which was purified by prep-HPLC (0655) (Phenomenex Gemini (150 mm x 25mm, 10 muiotaeta); A = H20 (0.05% NH4OH) and B = CH3CN); (0656) 53-65% B over 8 minutes) to afford Compound 13 (23.04 mg, 0.06 mmol) as a solid. *H NMR (400MHz, CDCI3) = 8.60 (d, 1H), 8.46 (s, 1H), 7.81 (s, 1H), 7.60 (d, 2H), 7.48 (d, 2H), 1.87 - 1.82 (m, 2H), 1.53 - 1.48 (m, 2H). LCMS R, = 1.23 min using Method B, MS ESI calcd. for Ci7H12F3N4 [M+H]+ 329.1, found 328.9.

Reference： [1]Patent: WO2018/98491,2018,A1 .Location in patent: Page/Page column 91-92

42
[ 1206641-31-7 ]
C₇H₃ClF₃N₃ [ No CAS ]
C₁₇H₁₁F₃N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
12.48 mg	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate; In 1,4-dioxane; water;	A mixture of A-22 (80 mg, 0.36 mmol), l-[4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)phenyl]cyclopropanecarbonitrile (126.33 mg, 0.47 mmol), Pd(dppf)Ci2.CH2Cl2 (58.97 mg, 0.07 mmol) and CS2CO3 (235.28 mg, 0.72 mmol) in 1,4-dioxane (3 mL) and water (0.5 mL) was stirred at 90 C for 16 hours. The mixture was filtered through silica gel and eluted with EtOAc (20 mL x 2). The filtrate was concentrated, and the residue was diluted with EtOAc (30 mL), washed with water (10 mL x 2) and brine (10 mL), dried over Na2S04, filtered and concentrated to give the crude product, which was purified by prep-TLC (silica gel, PE: EtOAc = 3:1) to afford Compound 22 (12.48 mg, 0.03 mmol) as a solid. *H NMR (400MHz, CDC13) = 9.21 (d, 1H), 8.34 (s, 1H), 7.99 - 7.86 (m, 3H), 7.44 (d, 2H), 1.85 - 1.79 (m, 2H), 1.53 - 1.46 (m, 2H). LCMS R, = 1.20 min using Method A, MS ESI calcd. for Ci7H12F3N4 [M+H]+ 329.1, found 328.9.

Reference： [1]Patent: WO2018/98491,2018,A1 .Location in patent: Page/Page column 100-101

43
[ 1206641-31-7 ]
C₉H₃BrF₃N₃ [ No CAS ]
C₁₉H₁₁F₃N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42.46 mg	With potassium phosphate; bis(tri-t-butylphosphine)palladium(0); In 1,4-dioxane; water; at 80.0℃; for 16.0h;	A mixture of A-27 (80 mg, 0.28 mmol), l-[4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)phenyl]cyclopropanecarbonitrile (89.09 mg, 0.33 mmol), Pd(i-Bu3P)2 (21.14 mg, 0.04 mmol) and K3PO4 (116.95 mg, 0.55 mmol) in 1,4-dioxane (2 mL) and water (0.20 mL) was stirred at 80 C for 16 hours. The mixture was diluted with EtOAc (5 mL), filtered through silica gel, eluted with EtOAc (5 mL) and concentrated to give the crude product, which was purified by flash chromatography on silica gel (PE: EtOAc = 5:1 to 1:1) to afford Compound 20 (42.46 mg, 0.11 mmol) as a solid. 1H NMR (400MHz, OMSO-d6) = 8.68 (s, 1H), 8.17 (d, 1H), 7.91 (dd, 1H), 7.83 (d, 2H), 7.50 (d, 2H), 1.86 - 1.80 (m, 2H), 1.61 - 1.56 (m, 2H). LCMS R, = 1.25 min using Method B, MS ESI calcd. for Ci9H12F3N4 [M+H]+ 353.1, found 353.1.

Reference： [1]Patent: WO2018/98491,2018,A1 .Location in patent: Page/Page column 99

44
[ 1206641-31-7 ]
C₆H₂ClF₃N₄ [ No CAS ]
C₁₆H₁₀F₃N₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77.03 mg	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate; In 1,4-dioxane; water; at 80.0℃; for 16.0h;	A mixture of <strong>[1206641-31-7]1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]cyclopropanecarbonitrile</strong> (199.54 mg, 0.74 mmol), A-72 (150 mg, 0.67 mmol), Pd(dppf)Cl2.CH2Cl2 (82.56 mg, 0.10 mmol) and Cs2C03 (439.43 mg, 1.35 mmol) in 1,4-dioxane (2 mL) and water (0.20 mL) was stirred at 80 C for 16 hours. The mixture was cooled to room temperature, diluted with EtOAc (5 mL), filtered through silica gel, eluted with EtOAc (5 mL) and concentrated to give the crude product, which was purified by flash chromatography on silica gel (PE: EtOAc = 5: 1 to 1 : 1) to afford Compound 67 (77.03 mg, 0.24 mmol) as a solid. H NMR (400MHz, DMSO-d6) _ = 9.76 (d, 1H), 9.01 (s, 1H), 8.20 (d, 2H), 7.49 (d, 2H), 1.86 -1.82 (m, 2H), 1.63 -1.59 (m, 2H). LCMS R, = 1.11 min using Method A, MS ESI calcd. for [M+H]+ 330.1, found 329.9 Example 64. Synthesis of Compound 68

Reference： [1]Patent: WO2018/98499,2018,A1 .Location in patent: Page/Page column 175

45
[ 1206641-31-7 ]
5-chloro-3-methyl-triazolo[1,5-a]pyridine [ No CAS ]
C₁₇H₁₄N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38%	With potassium phosphate; bis[tris( 1,1-dimethylethyl)phosphine]-palladium; In 1,4-dioxane; water; at 80.0℃; for 16.0h;	A mixture of 5-chloro-3-methyl-triazolo[1,5-a]pyridine (50 mg, 0.30 mmol), 1-[4-(4,4,5,5- tetramethyl- 1,3 ,2-dioxaborolan-2-yl)phenyl]cyclopropanecarbonitri le (102.1 mg, 0.36 mmol),PdQ-Bu3P)2 (22.87 mg, 0.04 mmol) and K3P04 (126.67 mg, 0.60 mmol) in 1,4-Dioxane (2 mL) and Water (0.2 mL) was stirred at 80 C for 16 hours to give a brown mixture. After cooling to room temperature, the suspension was diluted with EtOAc (10 mL), filtered through Celite and eluted with EtOAc (20 mL). And the combined filtrates were concentrated to give crude product. The crude product was purified by flash chromatographyon silica gel (EtOAc in PE = 20% to 70%) to give the product (32.6 mg, 0.11 mmol, 38% yield) as a solid. ?H NMR (400MHZ, DMSO-d6) oH = 9.02 (d, 1H), 8.25 (s, 1H), 7.90 (d, 2H), 7.51 - 7.44 (m, 3H), 2.59 (s, 3H), 1.84- 1.79 (m, 2H), 1.61 - 1.56 (m, 2H). LCMS R =1.02 mm in 2.0 mm chromatography, 10-8OAB, purity 100%, MS ESI calcd. for C17H15N4 [M+H] 275.1, found 274.9.

Reference： [1]Patent: WO2019/35951,2019,A1 .Location in patent: Page/Page column 53

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