[ CAS No. 910251-11-5 ] {[proInfo.proName]}

Name: 910251-11-5|Potassium trifluoro(methoxymethyl)borate|95%
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SKU: A215557
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2D 3D

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Quality Control of [ 910251-11-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 910251-11-5 ]

SDS Specification

Alternatived Products of [ 910251-11-5 ]

Product Details of [ 910251-11-5 ]

CAS No. :	910251-11-5	MDL No. :	MFCD10566517
Formula :	C₂H₅BF₃KO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WNVXSBCLLHGATG-UHFFFAOYSA-N
M.W :	151.97	Pubchem ID :	45588148
Synonyms :

Calculated chemistry of [ 910251-11-5 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	20.83
TPSA :	9.23 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.07 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	1.63
Log Po/w (WLOGP) :	2.28
Log Po/w (MLOGP) :	0.53
Log Po/w (SILICOS-IT) :	0.28
Consensus Log Po/w :	0.94

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	3.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.68
Solubility :	3.2 mg/ml ; 0.021 mol/l
Class :	Very soluble
Log S (Ali) :	-1.44
Solubility :	5.56 mg/ml ; 0.0366 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.24
Solubility :	8.83 mg/ml ; 0.0581 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.69

Safety of [ 910251-11-5 ]

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

Application In Synthesis of [ 910251-11-5 ]

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

Upstream synthesis route of [ 910251-11-5 ]
Downstream synthetic route of [ 910251-11-5 ]

[ 910251-11-5 ] Synthesis Path-Upstream 1~4

1
[ 27490-32-0 ]
[ 910251-11-5 ]

Yield	Reaction Conditions	Operation in experiment
18%	Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5 h; Stage #2: With Triisopropyl borate In tetrahydrofuran; hexane at -78 - 20℃; for 0.333333 h; Stage #3: With potassium hydrogen difluoride In tetrahydrofuran; hexane at 0℃;	To a mixture of tributyl-methoxymethyl-tin (360 mg, 1.1 mmol) and tetrahydrofuran (3 ml) was added dropwise n-butyllithium (1.5M n-hexane solution, 0.77 ml, 1.2 mmol) at -78°C (external temperature). The reaction mixture was stirred at the same temperature for 30 minutes. The mixture was added dropwise to a mixture of triisopropyl borate (0. 30 ml, 1.3 mmol) and tetrahydrofuran (5 ml) using a cannula at -78°C (external temperature). The reaction mixture was stirred at room temperature for 20 minutes. To the mixture was added potassium hydrogen fluoride (0.51 g, 6.5 mmol) at 0°C (external temperature). Then, water (60 ml) was added dropwise to the reaction mixture. The reaction mixture was raised to room temperature, and the solvent was distilled off under reduced pressure. The resulting residue was washed with diethyl ether. To the residue was added acetone, followed by filtration. After the solvent was distilled off from the filtrate under reduced pressure, the resulting residue was recrystallized using acetone to obtain the title compound (30 mg, 0.20 mmol, 18percent). ¹H-NMR Spectrum (DMSO-d₆) δ (ppm) : 2.39-2.43 (2H, m) , 3.05 (3H, s).

Reference： [1] Patent: EP1867650, 2007, A1, . Location in patent: Page/Page column 20

2
[ 124-41-4 ]
[ 910251-11-5 ]

Reference： [1] Organic Letters, 2008, vol. 10, # 11, p. 2135 - 2138

3
[ 67-56-1 ]
[ 910251-11-5 ]

Reference： [1] Organic Letters, 2011, vol. 13, # 15, p. 3948 - 3951

4
[ 67-56-1 ]
[ 910251-11-5 ]

Reference： [1] Journal of the American Chemical Society, 2016, vol. 138, # 22, p. 6936 - 6939

[ 910251-11-5 ] Synthesis Path-Downstream 1~50

1
[ 27490-32-0 ]
[ 910251-11-5 ]

Yield	Reaction Conditions	Operation in experiment
18%		To a mixture of tributyl-methoxymethyl-tin (360 mg, 1.1 mmol) and tetrahydrofuran (3 ml) was added dropwise n-butyllithium (1.5M n-hexane solution, 0.77 ml, 1.2 mmol) at -78C (external temperature). The reaction mixture was stirred at the same temperature for 30 minutes. The mixture was added dropwise to a mixture of triisopropyl borate (0. 30 ml, 1.3 mmol) and tetrahydrofuran (5 ml) using a cannula at -78C (external temperature). The reaction mixture was stirred at room temperature for 20 minutes. To the mixture was added potassium hydrogen fluoride (0.51 g, 6.5 mmol) at 0C (external temperature). Then, water (60 ml) was added dropwise to the reaction mixture. The reaction mixture was raised to room temperature, and the solvent was distilled off under reduced pressure. The resulting residue was washed with diethyl ether. To the residue was added acetone, followed by filtration. After the solvent was distilled off from the filtrate under reduced pressure, the resulting residue was recrystallized using acetone to obtain the title compound (30 mg, 0.20 mmol, 18%). 1H-NMR Spectrum (DMSO-d6) delta (ppm) : 2.39-2.43 (2H, m) , 3.05 (3H, s).

Reference： [1]Patent: EP1867650,2007,A1 .Location in patent: Page/Page column 20

2
[ 910251-11-5 ]
[ 2052-49-5 ]
tetrabutylammonium methoxymethyl trifluoroborate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	In dichloromethane; water; at 20℃;	To a solution of <strong>[910251-11-5]potassium methoxymethyl trifluoroborate</strong> (500 mg, 3.29 mmol), described in Example 2A, in a mixture of methylene.chloride (10 ml) and water (10 ml) was added tetrabutylammonium hydroxide (2.37 ml, 40% aqueous solution, 3.62 mmol) at room temperature, followed by stirring at room temperature for a few minutes. The mixed solution was extracted with methylene chloride, the resulting organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain the title compound (933 mg, 2.61 mmol, 80%). 1H-NMR Spectrum (DMSO-d6) delta (ppm) : 0.918 (12H, t, J=7.5 Hz) , 1.24-1.34(8H, m), 1.51-1.59(8H, m), 2.39(2H, q, J=5.2 Hz), 3.04(3H, s), 3.12-3.16(8H, m).

Reference： [1]Patent: EP1867650,2007,A1 .Location in patent: Page/Page column 30-31

3
[ 910251-11-5 ]
[ 17763-80-3 ]
[ 1515-83-9 ]

Yield	Reaction Conditions	Operation in experiment
68%	With caesium carbonate;palladium diacetate; tris-(o-tolyl)phosphine; In 1,4-dioxane; water; at 95℃; for 4h;	To a mixture of 4-nitrophenyl trifluoromethanesulfonate (30 mg, 0.11 mmol) and 1,4-dioxane (3 ml) were added water (0.3 ml), cesium carbonate (0.11 g, 0.34 mmol), <strong>[910251-11-5]potassium methoxymethyltrifluoroborate</strong> (17 mg, 0.11 mmol), palladium (II) acetate (1.3 mg, 0.0056 mmol) and tri-o-tolylphosphine (8.5 mg, 0.028 mmol). Then, the reaction mixture was stirred at 95C (external temperature) for 4 hours. After the reaction mixture was cooled at room temperature, water and heptane were added to the mixture, and the organic layer was separated. The organic layer was filtered, and the solvent was distilled off under reduced pressure. The residue was purified by NH-silica gel column chromatography (heptane:ethyl acetate=10:1) to obtain the title compound (13 mg, 0.078 mmol, 68%). 1H-NMR Spectrum (CDCl3) delta (ppm) : 3.45 (3H, s), 4. 56 (2H, s), 7.50 (2H, d, J=9.0Hz), 8.21(2H, d, J=8.8Hz).

Reference： [1]Patent: EP1867650,2007,A1 .Location in patent: Page/Page column 35

4
[ 910251-11-5 ]
[ 578-57-4 ]
[ 21998-86-7 ]

Yield	Reaction Conditions	Operation in experiment
66%	With caesium carbonate;dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; In 1,4-dioxane; water; at 100℃;	To a mixture of 2-bromoanisole (50 mg, 0.27 mmol) and 1,4-dioxane (2 ml) were added water (0.2 ml), cesium carbonate (0.26 g, 0.80 mmol), <strong>[910251-11-5]potassium methoxymethyl trifluoroborate</strong> (81 mg, 0.53 mmol), palladium (II) acetate (3.0 mg, 0.013 mmol) and 2-dicyclohexelphosphino-2',6'-dimethoxybiphenyl (11 mg, 0.027 mmol). Then, the reaction mixture was stirred at 100C (external temperature) overnight. After the reaction mixture was allowed to cool at room temperature, water and butane were added to the mixture, and the resultant was filtered using Celite. The organic layer was separated, and the organic layer was washed with an aqueous saturated sodium chloride solution. The organic layer was separated, and the solvent was distilled off under reduced pressure. The residue was purified by NH-silica gel column chromatography (heptane) to obtain the title compound (27 mg, 0.18 mmol, 66%). 1H-NMR Spectrum (CDCl3) delta (ppm) : 3.42 (3H, s), 3.84 (3H, s) , 4.51 (2H, s) , 6.87-6.89(1H, m) , 6.96(1H, td, J=7.4, 1.1Hz), 7.25-7.29(1H, m), 7.34-7.36(1H, m).

Reference： [1]Patent: EP1867650,2007,A1 .Location in patent: Page/Page column 35-36

5
[ 910251-11-5 ]
[ 99-90-1 ]
[ 22072-50-0 ]

Yield	Reaction Conditions	Operation in experiment
31%	With caesium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; at 100℃; for 7h;	To a mixture of 4'-bromoacetophenone (300 mg, 1.51 mmol) and1,4-dioxane (4ml) were added water (0.4ml), cesium carbonate (1.48 g, 4.54 mmol), <strong>[910251-11-5]potassium methoxymethyl trifluoroborate</strong> (459 mg, 3.02 mmol) and 1',1'-bis(diphenylphosphino)ferrocenedichloropalladium (II) (110 mg, 0.151 mmol). Then, the reaction mixture was stirred at 100C (external temperature) for 7 hours. After the reaction mixture was cooled at room temperature, water and methylene chloride were added to the mixture, followed by filtration using Celite. The separated organic layer was washed with an aqueous saturated sodium chloride solution. The organic layer was separated, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (heptane/ethyl acetate) to obtain the title compound (76 mg, 31%). 1H-NMR Spectrum (CDCl3) delta (ppm).: 2.61 (3H, s), 3.42 (3H, s), 4.52(2H, s), 7.41-7.45(2H, m), 7.93-7.97 (2H, m).

Reference： [1]Patent: EP1867650,2007,A1 .Location in patent: Page/Page column 38

6
[ 910251-11-5 ]
[ 619-42-1 ]
[ 1719-82-0 ]

Yield	Reaction Conditions	Operation in experiment
33%	With caesium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; at 100℃; for 4.5h;	To a mixture of methyl 4-bromobenzoate (50 mg, 0.233 mmol) and 1,4-dioxane (1 ml) were added water (0.1 ml), cesium carbonate (228 mg, 0.7 mmol), potassiummethoxymethyl trifluoroborate (71 mg, 0.467 mmol) and 1',1'-bis(diphenylphosphino)ferrocenedichloropalladium (II) (17 mg, 0.023 mmol). Then, the reaction mixture was stirred at 100C (external temperature) for 4.5 hours. After the reaction mixture was cooled at room temperature, water and methylene chloride were added to the mixture, followed by filtration using Celite. The separated organic layer was washed with an aqueous saturated sodium chloride solution. The organic layer was separated, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (heptane: ethyl acetate=10:1) to obtain the title compound (13.9 mg, 33%). 1H-NMRSpectrum (CDCl3) delta (ppm):3.41(3H,s),3.91(3H,s),4.51(2H, s), 7.39(2H, d, J=8.4 Hz), 7.99-8.03(2H, m) .

Reference： [1]Patent: EP1867650,2007,A1 .Location in patent: Page/Page column 38-39

7
[ 13195-50-1 ]
[ 910251-11-5 ]
[ 910251-46-6 ]

Yield	Reaction Conditions	Operation in experiment
11%	With caesium carbonate;palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In 1,4-dioxane; water; at 100℃; for 6h;	A mixture of <strong>[910251-11-5]potassium methoxymethyl trifluoroborate</strong> (33 mg, 0.22 mmol), 2-bromo-5-nitrothiophene (30 mg, 0.14 mmol), 1,4-dioxane (1.5 ml), water (0.15 ml), cesium carbonate (235 mg, 0.72 mmol) , palladium (II) acetate (3.2 mg, 0.014 mmol), and 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (9.0mg, 0.014 mmol) was stirred at 100C (external temperature) for 6 hours. After the reaction mixture was cooled at room temperature, water and ethyl acetate were added to the mixture, followed by filtration using Celite. The organic layer was washed with an aqueous saturated sodium chloride solution, and the solvent was distilled off under reduced pressure. The residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=3:1) to obtain the title compound (2.7 mg, 0.016 mmol, 11%). 1H-NMR Spectrum (CD3OD) delta (ppm): 3.43 (3H, s), 4.65 (2H, d, J=0.9 Hz), 7.04 (1H, dt, J=4.2, 0.9 Hz), 7.89(1H, d, J=4.2 Hz).

Reference： [1]Patent: EP1867650,2007,A1 .Location in patent: Page/Page column 41

8
[ 910251-11-5 ]
[ 949170-45-0 ]
[ 1123190-68-0 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate;palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In 1,4-dioxane; water; at 100℃;	Synthesis of (-)-2-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-8-(2-methoxymethylphenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridine and (+)-2-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-8-(2-methoxymethylphenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridinePotassium methoxymethyl trifluoroborate (CAS No. 910251-11-5, 372 mg), palladium acetate (7 mg), BINAP (19 mg) and cesium carbonate (1.2 g) were added to a mixed solution of 8-(2-bromophenyl)-2-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-a]pyridine (150 mg) in dioxane (7 mL) and water (0.7 mL). The reaction solution was stirred in a nitrogen atmosphere at 100 C. overnight. The reaction mixture was left to cool to room temperature. Then, water and ethyl acetate were added to the reaction mixture and the organic layer was separated. The resulting organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: heptane-ethyl acetate system) and further separated by CHIRALPAK AD-H manufactured by Daicel Chemical Industries, Ltd. (2 cm×25 cm, mobile phase: ethanol, flow rate: 10 mL/min) to obtain the title optically active compound with a retention time of 16 minutes and negative optical rotation (6.2 mg) and the title optically active compound with a retention time of 18 minutes and positive optical rotation (8 mg).The property values of the title optically active compound with a retention time of 16 minutes are as follows.1H-NMR (CDCl3) delta (ppm): 1.98-2.15 (m, 2H), 2.20-2.29 (m, 1H), 2.30 (s, 3H), 2.36-2.43 (m, 1H), 3.41 (s, 3H), 3.85 (s, 3H), 4.31 (t, J=5.6 Hz, 2H), 4.46 (dd, J=11.6 Hz, 1.6 Hz, 1H), 4.61 (t, J=6.4 Hz, 1H), 4.71 (dd, J=11.6 Hz, 1.6 Hz, 1H), 6.85-6.88 (m, 2H), 6.91 (t, J=1.2 Hz, 1H), 7.06 (dd, J=16 Hz, 1.6 Hz, 1H), 7.11-7.15 (m, 2H), 7.21 (dd, J=8 Hz, 1.6 Hz, 1H), 7.24-7.29 (m, 1H), 7.37-7.40 (m, 1H), 7.48 (dd, J=16 Hz, 1.6 Hz, 1H), 7.69 (t, J=1.6 Hz, 1H).The property values of the title optically active compound with a retention time of 18 minutes are as follows.1H-NMR (CDCl3) delta (ppm): 1.98-2.15 (m, 2H), 2.20-2.29 (m, 1H), 2.30 (s, 3H), 2.36-2.43 (m, 1H), 3.41 (s, 3H), 3.85 (s, 3H), 4.31 (t, J=5.6 Hz, 2H), 4.46 (dd, J=11.6 Hz, 1.6 Hz, 1H), 4.61 (t, J=6.4 Hz, 1H), 4.71 (dd, J=11.6 Hz, 1.6 Hz, 1H), 6.85-6.88 (m, 2H), 6.91 (t, J=1.2 Hz, 1H), 7.06 (dd, J=16 Hz, 1.6 Hz, 1H), 7.11-7.15 (m, 2H), 7.21 (dd, J=8 Hz, 1.6 Hz, 1H), 7.24-7.29 (m, 1H), 7.37-7.40 (m, 1H), 7.48 (dd, J=16 Hz, 1.6 Hz, 1H), 7.69 (t, J=1.6 Hz, 1H).
	With caesium carbonate;palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In 1,4-dioxane; water; at 100℃;Inert atmosphere;	Synthesis of (-)-2-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-8-(2-methoxymethylphenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridine and (+)-2-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-8-(2-methoxymethylphenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridine Potassium methoxymethyl trifluoroborate (CAS No. 910251-11-5, 372 mg), palladium acetate (7 mg), BINAP (19 mg) and cesium carbonate (1.2 g) were added to a mixed solution of 8-(2-bromophenyl)-2-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-a]pyridine (150 mg) in dioxane (7 mL) and water (0.7 mL). The reaction solution was stirred in a nitrogen atmosphere at 100C overnight. The reaction mixture was left to cool to room temperature. Then, water and ethyl acetate were added to the reaction mixture and the organic layer was separated. The resulting organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: heptane-ethyl acetate system) and further separated by CHIRALPAK AD-H manufactured by Daicel Chemical Industries, Ltd. (2 cm * 25 cm, mobile phase: ethanol, flow rate: 10 mL/min) to obtain the title optically active compound with a retention time of 16 minutes and negative optical rotation (6.2 mg) and the title optically active compound with a retention time of 18 minutes and positive optical rotation (8 mg). The property values of the title optically active compound with a retention time of 16 minutes are as follows. 1H-NMR (CDCl3) delta (ppm): 1.98-2.15 (m, 2H), 2.20-2.29 (m, 1H), 2.30 (s, 3H), 2.36-2.43 (m, 1H), 3.41 (s, 3H), 3.85 (s, 3H), 4.31 (t, J=5.6Hz, 2H), 4.46 (dd, J=11.6Hz, 1.6Hz, 1H), 4.61 (t, J=6.4Hz, 1H), 4.71 (dd, J=11.6Hz, 1.6Hz, 1H), 6.85-6.88 (m, 2H), 6.91 (t, J=1.2Hz, 1H), 7.06 (dd, J=16Hz, 1.6Hz, 1H), 7.11-7.15 (m, 2H), 7.21 (dd, J=8Hz, 1.6Hz, 1H), 7.24-7.29 (m, 1H), 7.37-7.40 (m, 1H), 7.48 (dd, J=16Hz, 1.6Hz, 1H), 7.69 (t, J=1.6Hz, 1H). The property values of the title optically active compound with a retention time of 18 minutes are as follows. 1H-NMR (CDCl3) delta (ppm): 1.98-2.15 (m, 2H), 2.20-2.29 (m, 1H), 2.30 (s, 3H), 2.36-2.43 (m, 1H), 3.41 (s, 3H), 3.85 (s, 3H), 4.31 (t, J=5.6Hz, 2H), 4.46 (dd, J=11.6Hz, 1.6Hz, 1H), 4.61 (t, J=6.4Hz, 1H), 4.71 (dd, J=11.6Hz, 1.6Hz, 1H), 6.85-6.88 (m, 2H), 6.91 (t, J=1.2Hz, 1H), 7.06 (dd, J=16Hz, 1.6Hz, 1H), 7.11-7.15 (m, 2H), 7.21 (dd, J=8Hz, 1.6Hz, 1H), 7.24-7.29 (m, 1H), 7.37-7.40 (m, 1H), 7.48 (dd, J=16Hz, 1.6Hz, 1H), 7.69 (t, J=1.6Hz, 1H).

Reference： [1]Patent: US2009/62529,2009,A1 .Location in patent: Page/Page column 65-66
[2]Patent: EP2181992,2010,A1 .Location in patent: Page/Page column 80

9
potassium bromomethyl trifluoroborate [ No CAS ]
[ 124-41-4 ]
[ 910251-11-5 ]

Reference： [1]Organic Letters,2008,vol. 10,p. 2135 - 2138

10
[ 623-03-0 ]
[ 910251-11-5 ]
[ 1515-85-1 ]

Reference： [1]Organic Letters,2008,vol. 10,p. 2135 - 2138

11
[ 910251-11-5 ]
[ 623-12-1 ]
[ 1515-81-7 ]

Reference： [1]Organic Letters,2008,vol. 10,p. 2135 - 2138

12
[ 491-35-0 ]
[ 910251-11-5 ]
4-methyl-2-quinolylmethyl methyl ether [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 4592 - 4595
Angew. Chem.,2019,vol. 131,p. 4640 - 4643,4
[2]Organic Letters,2011,vol. 13,p. 1852 - 1855

13
[ 67-56-1 ]
potassium chloromethyltrifluoroborate [ No CAS ]
[ 910251-11-5 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 3948 - 3951

14
[ 910251-11-5 ]
[ 38262-42-9 ]
[ 5903-23-1 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 3948 - 3951

15
[ 910251-11-5 ]
[ 1253573-76-0 ]
[ 1379860-77-1 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 5188 - 5219

16
[ 910251-11-5 ]
[ 1825-61-2 ]
[ 7677-24-9 ]
potassium methoxymethyldicyanomethoxyborate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80 mg	With chloro-trimethyl-silane; In acetonitrile; at 20℃; for 0.5h;	Example 10: Potassium methoxymethyldicyanomethoxyborate - K[CH3OCH2B(OCH3)(CN)2] <strong>[910251-11-5]K[CH3OCH2BF3]</strong> + 2 (CH3)3SiCN + (CH3)3SiOCH3 - CH3CN *- K[CH3OCH2B(OCH3)(CN)2] + 3 (CH3)3SiF <strong>[910251-11-5]K[CH3OCH2BF3]</strong> (70 mg, 0.461 mmol) is suspended in 10 mL of a mixture of (CH3)3SiCN (4.29 mmol, 0.57 mL), (CH3)3SiOCH3 (11.58 mmol, 1.59 mL), (CH3)3SiCI (0.79 mmol, 0.1 mL) and acetonitrile and stirred at room temperature for 30 minutes. Subsequently all volatile materials are removed in vacuo and a white solid is obtained. The yield of potassium methoxymethyldicyanomethoxyborate is 80 mg (0.45 mmol). The NMR spectra of K[CH3OCH2B(OCH3)(CN)2] are measured in CD3CN. 1 B{1H}-NMR; 1B-NMR; H{1 B}-NMR; <5, ppm: 3.23 s (CH2OCH3, 3H), 3.21 s (OCH3, 3H), 2.75 s (CH2, 2H). 1H-NMR; delta, ppm: = 3.23 s (CH2OCH3, 3H), 3.21 br. s (OCH3, 3H), 2.75 br. s (CH2, 2H).

Reference： [1]Patent: WO2013/10640,2013,A1 .Location in patent: Page/Page column 55; 56

17
[ 910251-11-5 ]
6-chloro-3-iodo-1-trityl-1H-pyrazolo[4,3-c]pyridine [ No CAS ]
6-chloro-3-(methoxymethyl)-1-trityl-1H-pyrazolo[4,3-c]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With chloro(2-dicyclohexylphosphino-2?,4?,6?-triisopropyl-1,1'-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II) methyl tert-butyl ether; palladium diacetate; caesium carbonate; In 1,4-dioxane; water; at 100℃; for 24h;Inert atmosphere;	Intermediate 52a 6-chloro-3-(methoxymethyI)-l-trityl-lH-pyrazolo[43-c]pyridine Under Argon, the solution of 6-cUoro-3-iodo-l-trityl-lH-pyrazolot4,3-c]pyridine (52 mg, 0.100 mmol), <strong>[910251-11-5]potassium methoxymethyltrifluoroborate</strong> (16.66 mg, 0.110 mmol), palladium(n) acetate (0.671 mg, 2.99 mupiiotaomicron), (2-DICYCLOHEXYLPHOSPfflNO-2',6'- DIISOPROPYL-l,l'-BIPHENYL)[2-(2-AMINOETHYL)PHENYL)]PALLADIUM(n) (4.36 mg, 5.98 mol) and cesium carbonate (0.024 ml, 0.299 mmol) in 1,4-Dioxane (0.9 ml) and Water (0.1 ml) was allowed to stir at 100 C for 24h. LC-MS showed the desired product's mass. EtOAc was added into the mixture and the organic layer was washed by water and brine. After drying over Na2S04 the organic layer was evaporated under reduced pressure yielding 6- c oro-3-(memoxymethyl)-l-1rityl-lH-pyrazolo[4,3-c]pyridine, 52a. The intermediate was taken to the next reaction without further purification. MS ESI Calc'd for C27H22CIN3O [M+H]+ 440, found 440.
	With palladium diacetate; caesium carbonate; In 1,4-dioxane; water; at 100℃; for 24h;	Under Argon, the solution of 6-chloro-3-iodo-1-trityl-1H-pyrazolo[4,3-c]pyridine (52 mg, 0.100 mmol), <strong>[910251-11-5]potassium methoxymethyltrifluoroborate</strong> (16.66 mg, 0.110 mmol), palladium(II) acetate (0.671 mg, 2.99 mumol), (2-DICYCLOHEXYLPHOSPHINO-2',6'-DIISOPROPYL-1,1'-BIPHENYL)[2-(2-AMINOETHYL)PHENYL)]PALLADIUM(II) (4.36 mg, 5.98 mumol) and cesium carbonate (0.024 ml, 0.299 mmol) in 1,4-Dioxane (0.9 ml) and Water (0.1 ml) was allowed to stir at 100 C for 24h. LC-MS showed the desired product's mass. EtOAc was added into the mixture and the organic layer was washed by water and brine. After drying over Na2SO4 the organic layer was evaporated under reduced pressure yielding 6-chloro-3-(methoxymethyl)-1-trityl-1H-pyrazolo[4,3-c]pyridine, 52a. The intermediate was taken to the next reaction without further purification. MS ESI Calc'd for C27H22ClN3O [M+H]+ 440, found 440.

Reference： [1]Patent: WO2013/63214,2013,A1 .Location in patent: Page/Page column 102
[2]Patent: EP2770987,2018,B1 .Location in patent: Paragraph 0360

18
[ 910251-11-5 ]
[ 1003320-22-6 ]
ethyl 2-(5-(methoxymethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
12 mg	With palladium diacetate; caesium carbonate; ruphos; In 1,4-dioxane; water;Reflux;	To a solution of 208A (300mg, O.lmmol) and <strong>[910251-11-5]potassium trifluoro(methoxymethyl)borate</strong> (304mg, 0.2 mmol) in 3 ml dioxane/water (10:1) was added 3 aq. Cs2C03 and 2- dicyclohexylphosphino-2',6'-diisopropoxybiphenyl (Ruphos)(93.4mg, 0.2 mmol) andPalladium(II)acetate (22.5 mg, 0.1 mmol). The resulting mixture was heated at reflux for overnight. The reaction mixture was filtered and the mixture was extracted with EtOAc. The organics were dried over Na2S04, filtered and concentrated. The crude product was purified by Si02 chromatography eluting with a gradient of EtOAc in hexanes to provide 12 mg of title compound. MS (m/z) 267 [M+H]+.

Reference： [1]Patent: WO2013/6738,2013,A1 .Location in patent: Page/Page column 313; 314

19
[ 910251-11-5 ]
5-bromo-2-ethyoxyl-benzonitrile [ No CAS ]
[ 1610416-56-2 ]

Yield	Reaction Conditions	Operation in experiment
24%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate; In 1,4-dioxane; water; at 100℃; for 16h;Inert atmosphere; Sealed tube;	1006241 Step B: Preparation of 2-ethoxy-5-(methoxymethyl)benzonitrile: A heavy walled pressure tube was charged with 5-bromo-2-ethoxybenzonitrile (0.500 g, 2.21 mmol), 8mls of dioxane and 2mls of water. Potassium methoxymethyltrifluoroborate (0.672 g, 4.42 mmol), PdCZ2(dppf) dichloromethane adduct (0.361 g, 0.442 mmol), and cesium carbonate (2.16 g, 6.64 mmol) were then added to the reaction mixture under a nitrogen atmosphere, the tube was sealed and heated to 100 C for 16 hours. After allowing to cool to ambient temperature, the mixture was diluted with EtOAc/water and filtered through GF/F filter paper. The organic layer was isolated from the filtrate, dried over sodium sulfate and concentrated under reduced pressure. The resulting crude material was purified by flash chromatography to give 2-ethoxy-5-(methoxymethyl)benzonitrile (0.100 g, 24% yield).

Reference： [1]Patent: WO2014/78331,2014,A1 .Location in patent: Paragraph 00624

20
[ 910251-11-5 ]
[ 1369886-14-5 ]
[ 1610416-92-6 ]

Yield	Reaction Conditions	Operation in experiment
36%	With palladium diacetate; caesium carbonate; ruphos; In 1,4-dioxane; water; at 100℃;Inert atmosphere;	[008691 Step E: Preparation of 2-(tert-butyl)-5-(methoxymethyl)benzonitrile: Charged a thick walled glass pressure vessel with 5-bromo-2-(tert-butyl)benzonitrile (520 mg, 2.18 mmol), dicyclohexyl(2?,6?-dimethoxy- [1,1 ?-biphenyl]-2-yl)phosphine (?S-Phos?) (179 mg, 0.437 mmol), Pd(OAc)2 (49.0 mg, 0.218 mmol), <strong>[910251-11-5]potassium (methoxymethyl)trifluoroborate</strong> (664 mg, 4.37 mmol), Cs2CO3 (2.8 g, 8.7 mmol), and 1:1 dioxane/water (10 mL). Sparged with N2 for several minutes, then heated to 100 C overnight with stirring. After cooling to ambient temperature, partioned mixture between EtOAc (20 mL) and water (20 mL). Separated phases, re-extracting aqueous with EtOAc (10 mL). Combined organics were washed with brine (20 mL), dried (MgSO4), filtered, and concentrated. The crude material was purified by Biotage Flash 40 silica gel column, eluting with a gradient of 5%-10% EtOAc/hexanes. Yield: 187 mg (36%).

Reference： [1]Patent: WO2014/78331,2014,A1 .Location in patent: Paragraph 00869

21
[ 910251-11-5 ]
[ 1610416-95-9 ]
5-cyclobutyl-2-(methoxymethyl)isonicotinonitrile [ No CAS ]
3-cyclobutyl-2,6-bis(methoxymethyl)isonicotinonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With manganese(III) triacetate dihydrate; trifluoroacetic acid; In water; acetic acid; at 60℃; for 3h;	1008751 Step D: Preparation of 5-cyclobutyl-2-(methoxymethyl)isonicotinonitrile:Charged a thick walled glass vessel plus stir bar with 3-cyclobutylisonicotinonitrile (1.0 g, 6.3 mmol), 1:1 acetic acidlwater (20 mL), trifluoroacetic acid (0.48 mL, 6.3 mmol), and <strong>[910251-11-5]potassium (methoxymethyl)trifluoroborate</strong> (1.92 g, 12.6 mmol). Stirred to dissolve, then added triacetoxymanganese dihydrate (4.24 g, 15.8 mmol). Heated to 60 C with stirring. After 1 hour, added more triacetoxymanganese dihydrate (4.24 g, 15.8 mmol), and continued heating for 2 hours. After cooling to ambient temperature, the reaction mixture was filtered through Celite, rinsing with EtOAc. Concentrated filtrate in vacuo. Performed a toluene azeotrope (2 x 20 mL) to remove excess acid and water. Partially purified crude mixture on a Redi-Sep 220 g silica gel column eluting with a gradient of neat DCM to 3% MeOH in DCM. Product containing fractions were re-purified by preparative TLC eluting with 5% MeOH in DCM. A second preparative TLC purification was performed to further enrich the concentration of the title compound in the mixture, eluting with 5% acetone in DCM. The title compound (260 mg) also contained 3-cyclobutylisonicotinonitrile (unreacted starting material) and 3 -cyclobutyl-2,6-bis(methoxymethyl)isonicotinonitrile by-product, and it was carried forward to the next step as a mixture.

Reference： [1]Patent: WO2014/78331,2014,A1 .Location in patent: Paragraph 00875

22
[ 910251-11-5 ]
[ 923281-52-1 ]
[ 1610416-59-5 ]

Yield	Reaction Conditions	Operation in experiment
28%	With palladium diacetate; caesium carbonate; ruphos; In 1,4-dioxane; water; at 100℃; for 16h;Sealed tube;	1006271 Step A: Preparation of 5-(methoxymethyl)-2-(trifluoromethoxy)benzaldehyde: A heavy walled pressure tube was charged with 5-bromo- 2-(trifluoromethoxy)benzaldehyde (1.00 g, 3.72 mmol), 37 mL of dioxane and 4 mL of water. Potassium methoxymethyltrifluoroborate (1.13 g, 7.43 mmol), palladium acetate (0.083 g, 0.372 mmol) S-Phos (0.305 g, 0.743 mmol), and cesium carbonate (4.84 g, 14.9 mmol) were then added, the tube was sealed and the mixture heated to 100C for 16 hours. After allowing to cool to ambient temperature, the mixture was diluted with EtOAc/water and filtered through GF/F filter paper. The organic layer was isolated from the filtrate, dried over sodium sulfate and concentrated under reduced pressure. The resulting crude material was purified by flash chromatography to give 5-(methoxymethyl)-2- (trifluoromethoxy)benzaldehyde as an oil (0.240 g, 28%).

Reference： [1]Patent: WO2014/78331,2014,A1 .Location in patent: Paragraph 00627

23
[ 910251-11-5 ]
[ 166978-46-7 ]
[ 1610345-66-8 ]

Yield	Reaction Conditions	Operation in experiment
18.8%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate; In 1,4-dioxane; water; at 100 - 120℃; for 21h;Inert atmosphere; Sealed tube;	Potassium methoxymethyltrifiuoroborate (1.20 g, 7.90 mmol), 7-bromo-4,4- dimethyl-3,4-dihydronaphthalen-l(2H)-one (1.00 g, 3.95 mmol), Dichloro[l,l'- bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (0.645 g, 0.790 mmol) and Cs2C03 (6.44 g, 19.8 mmol) were combined in dioxane (2 mL) and water (0.5 mL) and degassed by bubbling N2 through the solution for 10 minutes, The reaction was then sealed in a glass tube and heated in a 100 C sand bath for 6 hours and then in a 120 C sand bath for 15 hours. The reaction was cooled, poured into brine (50 mL) and extracted with EtOAc (2x100 mL). The combined organic extracts were concentrated and purified by silica gel column (0-10% EtOAc/hexanes) to afford 7-(methoxymethyl)-4,4-dimethyl-3,4-dihydronaphthalen-l(2H)-one (162 mg, 0.742 mmol, 18.8 % yield). MS (apci) m/z - 219.1 (M+H).

Reference： [1]Patent: WO2014/78454,2014,A1 .Location in patent: Paragraph 00775

24
[ 910251-11-5 ]
[ 1610343-22-0 ]
[ 1610343-44-6 ]

Yield	Reaction Conditions	Operation in experiment
53%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate; In 1,4-dioxane; water; at 100℃; for 16h;Inert atmosphere;	Potassium methoxymethyltrifluoroborate (12 mg, 0.079 mmol), l-(6- bromoisochroman-4-yl)-3-( 1 ',4-dimethyl- 1 -phenyl- 1 H, 1 - [3 ,4'-bipyrazol]-5-yl)urea (20 mg, 0.039 mmol), Dichloro[l, -bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (6.4 mg, 0.0079 mmol) and Cs2C03 (64 mg, 0.20 mmol) were combined in dioxane (2 mL) and water (0.5 mL) in a pressure tube and degassed by bubbling N2 through the mixture for 10 minutes, The reaction was sealed and heated at 100 C for 16 hours, cooled, poured into brine (10 mL), and extracted with EtOAc (2 x 10 mL). The combined organic extracts were concentrated and purified by reverse-phase column chromatography using 0-70% acetonitrile/H20 as the eluent to provide the title compound (9.8 mg, 0.021 mmol, 53% yield). MS (apci) m/z = 473.2 (M+H).

Reference： [1]Patent: WO2014/78454,2014,A1 .Location in patent: Paragraph 00847

25
[ 910251-11-5 ]
[ 1610343-46-8 ]
[ 1610343-47-9 ]
[ 1610343-48-0 ]

Yield	Reaction Conditions	Operation in experiment
9.1%; 8.8%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate; In 1,4-dioxane; water; at 100℃; for 3h;Inert atmosphere;	Potassium methoxymethyltrifluoroborate (18 mg, 0.12 mmol), l-(6- bromospiro[chroman-2, 1 '-cyclobutan] -4-yl)-3 -( 1 ',4-dimethyl- 1 -phenyl- 1 H, 1 -[3 ,4'-bipyrazol] - 5-yl)urea (Example 34; 33 mg, 0.060 mmol), dichloro[l,l'-bis(diphenylphosphino)- ferrocene]palladium (II) dichloromethane adduct (9.8 mg, 0.012 mmol) and Cs2C03 (98 mg, 0.30 mmol) were combined in dioxane (2 mL) and water (0.5 mL) and degassed by bubbling N2 through the mixture for 10 minutes, The reaction was then sealed in a glass tube and heated at 100 C for 3 hours. The reaction was cooled, poured into brine (10 mL) and extracted with EtOAc (2 x 10 mL). The combined organic extracts were concentrated and purified by reverse- phase column chromatography using 0-70% acetonitrile/H20 as the eluent to provide the title compounds: l-(l',4-dimethyl-l-phenyl-lH,rH-[3,4'-bipyrazol]-5-yl)-3-(6- (methoxymethyl)spiro[chroman-2, -cyclobutan]-4-yl)urea [second peak, 2.8 mg, 0.0055 mmol, 9.1% yield, MS (apci) m/z = 513.3 (M+H)] and l-(l',4-dimethyl-l-phenyl-lH,l'H-[3,4'- bipyrazol]-5-yl)-3-(spiro[chroman-2, -cyclobutan]-4-yl)urea [first peak, 2.50 mg, 0.0053 mmol, 8.8% yield, MS (apci) m/z = 469.2 (M+H)].

Reference： [1]Patent: WO2014/78454,2014,A1 .Location in patent: Paragraph 00852

26
[ 910251-11-5 ]
6-bromo-4-fluoro-2-(4-fluorophenyl)-5-isopropoxy-N-methylbenzofuran-3-carboxamide [ No CAS ]
4-fluoro-2-(4-fluorophenyl)-5-isopropoxy-6-(methoxymethyl)-N-methylbenzofuran-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In water; toluene; at 85℃; for 48h;Inert atmosphere;	4-Fluoro-2-(4-fluorophenyl)-5-isopropoxy-6-(methoxymethyl)-N- methylbenzofuran-3-carboxamide A mixture of 6-bromo-4-fluoro-2-(4-fluorophenyl)-5-isopropoxy-N- methylbenzofuran-3-carboxamide (600 mg, 1.414 mmol) , <strong>[910251-11-5]potassium methoxymethyltrifluoroborate</strong> (2149 mg, 14.14 mmol), PdCl2(dppf) (310 mg, 0.424 mmol) and cesium carbonate (2074 mg, 6.36 mmol) in a mixture of toluene (60 mL) and water (20 ml) was flushed with N2 and then stirred at 85C for 48 hrs. The mixture was diluted wih EtOAc (200 mL). The water layer was removed. The organic layer was filtered and then concentrated to give a crude solid, which was purified by column chromatography (Biotage 25m, EtOAc/Hexane = 0 to 30%) to give 280 mg (51 %) of the product as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) delta 7.99 - 7.92 (m, 2H), 7.41 (s, 1H), 7.21 - 7.13 (m, 2H), 6.12 (br. s., 1H), 4.62 (d, J=0.5 Hz, 2H), 4.56 - 4.47 (m, 1H), 3.51 - 3.47 (m, 3H), 3.07 (d, J=5.0 Hz, 3H), 1.37 (m, 6H). LCMS R, = 3.151 min., m/z 390 (M + H). The LC/MS data was obtained on a Shimadzu analytical LC /Micromass Platform LC (ESI+) at 220nm using the following set of conditions: Phenomenex Luna 3muiotaeta C18, 2 x 50 mm column, with a gradient of 0-100%B (B = 90% HPLC grade acetonitrile/ 0.1% trifluoro acetic acid/ 10% HPLC grade water), (A = 90% HPLC grade water / 0.1% trifluoroacetic acid/ 10% HPLC grade acetonitrile), in 4 minutes with a 1 minute hold at a rate of 0.8 mL/minute.

Reference： [1]Patent: WO2014/159559,2014,A1 .Location in patent: Page/Page column 53-54

27
[ 910251-11-5 ]
5-bromo-N-(3-cyano-4-fluoro-phenyl)-3-fluoro-1-methyl-4-[[(1R)-2,2,2-trifluoro-1-methyl-ethyl]sulfamoyl]pyrrole-2-carboxamide [ No CAS ]
N-(3-cyano-4-fluoro-phenyl)-3-fluoro-5-(methoxymethyl)-1-methyl-4-[[(1R)-2,2,2-trifluoro-1-methyl-ethyl]sulfamoyl]pyrrole-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20 mg	With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In 1,2-dimethoxyethane; water; at 140 - 160℃; for 1.58333h;Inert atmosphere; Microwave irradiation;	Nitrogen was bubbled through a mixture of compound 301 (prepared similarly as described in the synthesis of 301, but on a larger scale, 100.1 mg, 0.194 mmol) <strong>[910251-11-5]potassium trifluoro(methoxymethyl)borate</strong> (88.6 mg, 0.58 mmol), Cs2CO3 (189.9 mg, 0.58 mmol), DME (3mL, 29.Ommol), water (distilled, 0.25 mL) during 5 minutes. Then tetrakis(triphenylphosphine)palladium(0) (44.9 mg, 0.039 mmol) was added and the reaction mixture was heated at 140C during 30 minutes by microwave irradiation. The reaction mixture was further heated by microwave irradiation for 60 mm at 160C and next the reaction mixture was concentrated. The residue was dissolved in EtOAc (50 mL) and water (50 mL) The organiclayer was dried over magnesium sulphate, filtered and concentrated. The obtained residue was purified by silica gel column chromatography using a gradient from 10 till 100% EtOAc in heptane. The product fractions were concentrated and further purified by prep HPLC (Stationary phase: RP XBridge Prep C18 0DB- 5im,30x250mm, Mobile phase: 0.25% NH4HCO3 solution in water, CH3CN) yielding compound 309 (20 mg) as a white powder after dryingovernight in vacuo at 50C. Method D: Rt: 1.91 mm mlz: 479.1 (M-H) Exact mass: 480.1.Differential scanning calorimetry: From 30 to 300C at 10C/mm: peak at 180.7C. ?HNMR(400 MHz, DMSO-d6) oe ppm 1.16 (d, J=7.0 Hz, 3 H), 3.31 (s, 3 H), 3.77 (s, 3 H), 3.90 - 4.02 (m,1 H), 4.64 - 4.73 (m, 2 H), 7.55 (t, J=9.1 Hz, 1 H), 7.96 (ddd, J9.2, 4.9, 2.6 Hz, 1 H), 8.18 (dd,J5.7, 2.6 Hz, 1 H), 8.69 (d, J8.4 Hz, 1 H), 10.54 (s, 1 H).

Reference： [1]Patent: WO2014/184350,2014,A1 .Location in patent: Page/Page column 202

28
[ 910251-11-5 ]
tert-butyl 8-bromo-3,4,6,7-tetrahydro[1,4]diazepino[6,7,1-hi]indole-2(1H)-carboxylate [ No CAS ]
tert-butyl 8-(methoxymethyl)-1,2,3,4,6,7-hexahydro[1,4]diazepino[6,7,1-hi]indole-2(1H)-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With palladium diacetate; caesium carbonate; catacxium A; In 1,4-dioxane; water; at 80℃; for 15h;	To a mixture of tert-butyl 8-bromo-3,4,6,7-tetrahydro-[l,4]diazepino[6,7,l- i;']indole-2(lH)- carboxylate (25.8 mg, 73.04 muiotaetaomicron), <strong>[910251-11-5]potassium trifluoro(methoxymethyl)borate</strong> (22.20 mg, 0.146 mmol), Cesium carbonate (59.86 mg, 0.183 mmol), and Palladium (II) Acetate (1.640 mg, 7.3 muiotaetaomicron) in Dioxane (0.5 mL) and H20 (0.05 mL) was added di((3S,5S,7S)-adamantan-l-yl)(butyl)phosphine (3.928 mg, 10.96 muiotaetaomicron). The reaction was stirred at 80 C for 15 h. The mixture was filtered by syringe filter. The filtrate was purified by HPLC to give tert-butyl 8-(methoxymethyl)-3,4,6,7- tetrahydro-[l,4]diazepino[6,7,l-/i;]indole-2(lH)-carboxylate. LCMS m/z = 319.4 [M+l]+.

Reference： [1]Patent: WO2015/66344,2015,A1 .Location in patent: Page/Page column 244

29
[ 910251-11-5 ]
3-chloro-6-(4-(2,4-difluorophenoxy)piperidin-1-yl)-5-(isopropylamino)pyrazine-2-carbonitrile [ No CAS ]
[ 76-05-1 ]
6-(4-(2,4-difluorophenoxy)piperidin-1-yl)-5-(isopropylamino)-3-(methoxymethyl)pyrazine-2-carbonitrile trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
10%		j0288j Combined 3 -chloro-6-(4-(2,4-difluorophenoxy)piperidin- l-yl)-5-(isopropylamino)pyrazine-2-carbonitrile (50 mg, 0.123 mmol), PdC12(dppf) (8.97 mg, 0.0 12 mmol), <strong>[910251-11-5]potassium methoxymethyltrifluoroborate</strong> (74.5 mg, 0.490 mmol) and 2N Na2CO3 (0.5 ml) in dioxane (1.0 mL). The reaction mixture was heated in a microwave at 130 C for 30 mm. The reaction mixture was filtered and purified by HPLC using Method A twice to afford the title compound as its TFA salt (6 mg, 10%) as a yellow film. 1H NMR (500 MHz, methanol-d4) ppm 1.27 (d, J=6.35 Hz, 6 H) 1.87 - 2.04 (m, 2 H) 2.08 - 2.20 (m, 2 H) 3.05 (ddd, J=12.45, 8.54, 3.42 Hz, 2 H) 3.37 - 3.50 (m, 2 H) 4.28 - 4.41 (m, 1 H) 4.43 - 4.53 (m, 3 H) 6.80 - 6.93 (m, 1 H) 6.98 (ddd, J=11.35, 8.66, 2.93 Hz, 1 H) 7.17 (td, J=9.28, 5.37 Hz, 1 H) ; ESI-MS mlz [M+H]+ 418.4.

Reference： [1]Patent: WO2015/123533,2015,A1 .Location in patent: Paragraph 0103; 0286; 0287; 0288

30
[ 910251-11-5 ]
tert-butyl 10-bromo-8-cyclopropyl-3,4,7,8-tetrahydro-1H-[1,4]diazepino[6,7,1-ij]quinoline-2(6H)-carboxylate [ No CAS ]
tert-butyl 8-cyclopropyl-10-(methoxymethyl)-3,4,7,8-tetrahydro-1H-[1,4]diazepino[6,7,1-ij]quinoline-2(6H)-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With palladium diacetate; caesium carbonate; XPhos; In 1,4-dioxane; water; at 130℃; for 40h;Inert atmosphere; Microwave irradiation;	Under an argon atmosphere a mixture of 70 mg of tert-butyl 10-bromo-8-cyclopropyl-3,4,7,8-tetrahydro-1H-[1,4]diazepino[6,7,1-ij]quinoline-2(6H)-carboxylate (0.172 mmol, 1.00 eq) from step 8.2, 52.2 mg of potassium trifluoro (2-methoxymethyl)borate (0.344 mmol, 2.00 eq), 168 mg of cesium carbonate (0.516 mmol, 3.00 eq), 1.43 mg of Pd(OAc)2 (0.006 mmol, 0.04 eq) and 5.73 mg of X-Phos (0.012 mmol, 0.07 eq) in degassed dioxane (4 mL) and water (0.5 mL) was heated in a microwave at 130 C. for 40 h. Then the mixture was extracted with DCM and the organic phase was washed with water and dried over MgSO4, filtrated and solvent was evaporated to yield the title compound. ESI-MS: m/z (%): 373.30 (100, [M+H]+).

Reference： [1]Patent: US2015/259343,2015,A1 .Location in patent: Paragraph 0451-0452

31
[ 910251-11-5 ]
6-bromo-N-[trans-4-(morpholin-4-yl)cyclohexyl]quinazolin-4-amine [ No CAS ]
6-(methoxymethyl)-N-((1r,4r)-4-morpholinocyclohexyl)quina-zolin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
9%	With caesium carbonate; In 1,4-dioxane; water; at 85℃;Inert atmosphere;	A 100-mL round-bottom flask charged with compound 1-2 (100 mg, 0.26 mmol, 1.00 equiv), p and <strong>[910251-11-5]potassium methoxylmethyltrifluoroborate</strong> (77.9 mg, 0.51 mmol, 2.00 equiv) in dioxane (30 mL) and water (3 mL). Then Pd(pddf)Cl2 (50 mg) and Cs2C03 (250 mg, 0.76 mmol, 3.00 equiv) were added and the resulting mixture was degassed three times with nitrogen and stirred overnight at 85C. The resulting mixture was diluted with 30 mL of water and was extracted with 3 x 50 mL of ethyl acetate. Organic layers were combined, washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product was purified by preparative HPLC to furnish 8.2 mg (9%) of 6-(methoxymethyl)-N-((lr,4r)-4- morpholinocyclohexyl)quina-zolin-4-amine, 1-32 as a white solid. LCMS (ES, m/z): 357.2 [M+H]+; 1H NMR (300 MHz, CD3OD) delta 8.43 (s, 1H), 8.19 (s, 1H), 7.77 (dd, 1H), 7.69 (d, 1H), 4.62 (s, 2H), 4.26-4.19 (m, 1H), 3.74 (t, 4H), 3.45 (s, 3H), 2.66 (t, 4H), 2.39 (d, 1H), 2.39 (d, 2H), 2.34 (d, 2H), 1.62-1.42 (m, 4H).

Reference： [1]Patent: WO2015/164374,2015,A1 .Location in patent: Paragraph 00370; 00371

32
[ 910251-11-5 ]
methyl 6-(benzyloxy)-7-bromopyrazolo[1,5-a]pyridine-3-carboxylate [ No CAS ]
methyl 6-(benzyloxy)-7-(methoxymethyl)pyrazolo[1,5-a]pyridine-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19%		A pressure vial was charged with Intermediate 47 (350 mg, 0.969 mmol), <strong>[910251-11-5]potassium (methoxymethyl)trifluoroborate</strong> (295 mg, 1.94 mmol), RuPhos-Pd G2 (37.6 mg, 0.048 mmol) and cesium carbonate (947 mg, 2.91 mmol). The mixture was degassed (3x, vacuumlAr). Then dioxane (10 mL) and water (1.000 mL) were added, and the reaction mixture was degassed again. The pressure vial was capped, and the reactionmixture was stirred at 100 C for 18 h. Additional amounts of <strong>[910251-11-5]potassium (methoxymethyl)trifluoroborate</strong> (295 mg, 1.938 mmol), SPhos-Pd G2 (34.7 mg, 0.048 mmol), and cesium carbonate (947 mg, 2.91 mmol) were added. The reaction mixture was degassed (3x vacuumlAr), the pressure vial was capped, and the reaction mixture was stirred at 100 C for 18 h. Additional amount of SPhos-Pd G2 (34.7 mg, 0.048 mmol) wasadded, the reaction mixture was degassed, and was stirred at 125 C for 18 h. The reaction mixture was diluted with EtOAc, and CELITE was added. Solvent was removed under reduced pressure, and the residue was purified by flash chromatography (solid loading on CELITE) to give Intermediate 56A (61 mg, 19% yield) as an off-white solid. MS(ESI) m/z: 327.0 (M+H) ?H NMR (500MHz, DMSO-d6) oe ppm 8.44 (s, 1H), 8.09 (d, J=9.6Hz, 1H), 7.81 (d, J=9.6 Hz, 1H), 7.51 - 7.46 (m, 2H), 7.44 - 7.38 (m, 2H), 7.37 - 7.31 (m,1H), 5.28 (s, 2H), 4.94 (s, 2H), 3.83 (s, 3H), 3.32 (s, 3H).

Reference： [1]Patent: WO2016/10950,2016,A1 .Location in patent: Page/Page column 198; 199

33
[ 910251-11-5 ]
[ 1384535-97-0 ]
C₂₀H₂₀N₂O₂ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 6936 - 6939

34
[ 910251-11-5 ]
[ 1384535-97-0 ]
(R)-4-methoxy-3-phenyl-1-(1-phenyl-1H-imidazol-2-yl)butan-1-one [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 6936 - 6939

35
potassium bromomethyl trifluoroborate [ No CAS ]
[ 67-56-1 ]
[ 910251-11-5 ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 6936 - 6939

36
[ 910251-11-5 ]
(8-bromo-5,11-dihydro-6H-pyrido[2,3-b][1,5]benzodiazepin-6-yl)(trans-4-methoxycyclohexyl)methanone [ No CAS ]
[ 76-05-1 ]
6-[(trans-4-methoxycyclohexyl)carbonyl]-8-(methoxymethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A vial was charged with (8-bromo-5,ll -dihydro-6H-pyrido [2,3-b] [1,5 ]benzodiazepin-6- yl)Qrans-4-methoxycyclohexyl)methanone (25 mg, 0.060 mmol), <strong>[910251-11-5]potassium trifluoro(methoxymethyl)borate</strong> (11 mg, 0.075 mmol), mesylate[(di( 1 -adamantyl)-nbutylphosphine)-2-(2?-amino- 1,1 ?-biphenyl)]palladium(II), [(di( 1 -adamantyl)-butylphosphine)-2- (2?-amino-l,l?-biphenyl)]palladium(II) methanesulfonate (4.4 mg, 6.0 jimol) and cesiumcarbonate (59 mg, 0.18 mmol). The solids were dissolved in 2-methyl-2-butanol (0.5 mL) andwater (0.125 mL), the reaction was purged under argon for 5 minutes, and then heated to 70C for 18 h. The reaction was then allowed to cool to room temperature and concentrated under reduced pressure. The residue was filtered and purified by mass triggered reverse phase HPLC (ACN/water with 0.1% TFA modifier) to afford the title compound as a solid TFA salt. MS: 382 (M + 1). ?H NMR (600 MHz, DMSO-d6) oe 9.61 (s, 1H), 8.04 - 8.00 (m, 1H), 7.51 (d, J= 7.1 Hz,1H),7.29-7.26(m, 1H),7.19-7.16(m,2H),6.76-6.71 (m, 1H),5.17 (d,J= 15.0Hz, 1H),4.33 (s, 2H), 3.88 (d, J 14.9 Hz, 1H), 3.20 (s, 3H), 3.09 (s, 3H), 2.95 - 2.85 (m, 1H), 2.38 -2.31 (m, 1H), 1.98-1.90 (m, 1H), 1.84- 1.79 (m, 1H), 1.76- 1.70 (m, 1H), 1.48-1.37 (m,1H), 1.17- 1.08 (m, 1H), 0.99 -0.90 (m, 1H), 0.86- 0.76 (m, 1H), 0.62- 0.51 (m, 1H).

Reference： [1]Patent: WO2016/89797,2016,A1 .Location in patent: Page/Page column 219; 220

37
[ 910251-11-5 ]
4-chloro-2-(4-chlorophenyl)-N-[3-(1H-imidazol-2-yl)propyl]quinazoline-7-carboxamide [ No CAS ]
2-(4-chlorophenyl)-N-[3-(1H-imidazol-2-yl)propyl]-4-(methoxymethyl)quinazoline-7-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
10%	With caesium carbonate; In 1,4-dioxane; water; at 155℃; for 1.33333h;Inert atmosphere; Microwave irradiation;	4-Chloro-2-(4-chlorophenyl)-N-[3-(lH-imidazol-2-yl)propyl]quinazoline-7-carboxamide (200 mg, 0.0005 mol)(INT-5 described in Example 7), potassiummethoxymethyltrifluoroborate (214 mg, 0.00141 mol) dicesium carbonate (458 mg, 0.00141 mol) and SiliaCat DPP-Pd(0.260 mmol/g loading; 361 mg, 0.0000938 mol) were weighed into a 2-5mL microwave vial purged with nitrogen 5 min then added 1,4-dioxane (7.65 mL, 0.0980 mol) and water (1.69 mL, 0.0938 mol). The mixture was heated at 155 C for 80 min under microwave irradiation. After cooling, the reaction mixture was poured into EtOAc and water. The layers were separated and the aqueous layer was extracted two more times with EtOAc. The combined organic layer was dried over anhydrous MgSC>4 and concentrated in vacuo, and purified by HPLC to give 2-(4-chlorophenyl)-N-[3-(lH-imidazol-2-yl)propyl]-4- (methoxymethyl)quinazoline-7-carboxamide (20.0 mg, 10%) as a white solid. LCMS (ESI+): m/z = 436.2 (M+H). lH NMR (400 MHz, DMSO-dg) delta 9.12 (s, 1H), 8.63 - 8.56 (m, 3H), 8.45 (d, J= 8.6 Hz, 1H), 8.16 (s, 1H), 8.13 (d, J= 8.7 Hz, 1H), 7.68 (d, J= 8.6 Hz, 2H), 6.91 (s, 2H), 5.13 (s, 2H), 3.48 (s, 3H), 3.32-3.44 (m, 2H), 2.73 (t, J = 7.5 Hz, 2H), 2.01 - 1.93 (m, 2H).

Reference： [1]Patent: WO2016/118565,2016,A1 .Location in patent: Paragraph 00266

38
[ 910251-11-5 ]
tert-butyl 7-bromo-4,4a,5,6-tetrahydro-1H-pyrazino[1,2-a]quinoline-3(2H)-carboxylate [ No CAS ]
tert-butyl 7-(methoxymethyl)-4,4a,5,6-tetrahydro-1H-pyrazino[1,2-a]quinoline-3(2H)-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With palladium diacetate; caesium carbonate; catacxium A; In 1,4-dioxane; water; at 80℃; for 15h;	A mixture of tert-butyl 7-bromo-4,4a,5,6-tetrahydro-1H-pyrazino[1,2-a]quinoline-3(2H)-carboxylate (16d, 25 mg, 68 mmol), <strong>[910251-11-5]potassium trifluoro(methoxymethyl)borate</strong> (21 mg, 136 mmol), Pd(OAc)2 (1.5 mg, 6.8 mumol), di(1-adamantyl)-n-butylphosphine (3.7 mg, 10.2 mmol) and Cs2CO3 (56 mg, 0.170 mmol) in dioxane (0.5 mL) containing H2O (50 mL) was heated to 80 C for 15 h. The mixture was diluted with EtOAc and washed sequentially with sat. aq. NH4Cl and brine. The organics were dried over Na2SO4, filtered, and concentrated. Purification by silica gel chromatography (5% EtOAc in hexanes gradient to 50% EtOAc in hexanes) gave the tert-butyl 7-(methoxymethyl)-4,4a,5,6-tetrahydro-1H-pyrazino[1,2-a]quinoline-3(2H)-carboxylate LCMS (ESI+): m/z 333.4 [M + H]+.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 5877 - 5882

39
[ 910251-11-5 ]
ethyl 6-bromoquinoline-4-carboxylate [ No CAS ]
ethyl 6-(methoxymethyl)quinoline-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	With cyclopentyl methyl ether; palladium diacetate; caesium carbonate; ruphos; In water; at 100℃;	A solution of from step a (767 mg, 2.75 mmol), <strong>[910251-11-5]potassium trifluoro(methoxymethyl)borate</strong> (1.25 g, 8.25 mmol), Pd(OAc)2 (123 mg, 0.55 mmol), RuPhos (513 mg, 1.1 mmol), andC52CO3 (2.68 g, 8.25 mmol) was dissolved in degassed CPME (4.0 mL) and H20 (1.0 mL), then the mixture was stirred at 100 C overnight under N2. It was concentrated, and purifiedby silica gel chromatography with PE:EA=5: ito obtain ethyl 6-(methoxymethyl)quinoline-4- carboxylate as an orange oil (206 mg, 3 0%). ESI MS m/z = 245.5 [M+Hf
206 mg	With palladium diacetate; caesium carbonate; ruphos; In water; at 100℃;Inert atmosphere;	A solution of from step a (767 mg, 2.75 mmol), <strong>[910251-11-5]potassium trifluoro(methoxymethyl)borate</strong> (1.25 g, 8.25 mmol), Pd(OAc)2 (123 mg, 0.55 mmol), RuPhos (513 mg, 1.1 mmol), and Cs2CO3 (2.68 g, 8.25 mmol) was dissolved in degassed CPME (4.0 mL) and H2O (1.0 mL), then the mixture was stirred at 100C overnight under N2. It was concentrated, and purified by silica gel chromatography with PE:EA=5:1 to obtain ethyl 6-(methoxymethyl)quinoline-4- carboxylate as an orange oil (206 mg, 30%). ESI MS m/z = 245.5 [M+H]+.

Reference： [1]Patent: WO2017/15449,2017,A1 .Location in patent: Page/Page column 307
[2]Patent: WO2019/67864,2019,A1 .Location in patent: Page/Page column 280

40
[ 910251-11-5 ]
rac-tert-butyl {1-[({6-bromo-8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridin-3-yl}carbonyl)amino]-2-methylbutan-2-yl}carbamate [ No CAS ]
rac-tert-butyl {1-[({8-[(2,6-difluorobenzyl)oxy]-6-(methoxymethyl)-2-methylimidazo[1,2-a]pyridin-3-yl}carbonyl)amino]-2-methylbutan-2-yl}carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With palladium diacetate; caesium carbonate; ruphos; In 1,4-dioxane; water; at 100℃; for 18h;Inert atmosphere; Sealed tube;	Example 9A rac-tert-Butyl {1-[({8-[(2,6-difluorobenzyl)oxy]-6-(methoxymethyl)-2-methylimidazo[1,2-a]pyridin-3-yl}carbonyl)amino]-2-methylbutan-2-yl}carbamate A mixture of 100 mg (0.17 mmol) of rac-tert-butyl {1-[(6-bromo-8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridin-3-yl}carbonyl)amino]-2-methylbutan-2-yl carbamate (Example 5A), 29 mg (0.19 mmol) of <strong>[910251-11-5]potassium (methoxymethyl)trifluoroborate</strong>, 1.9 mg (0.008 mmol) of palladium(II) acetate, 8.0 mg (0.017 mmol) of RuPhos and 168 mg (0.52 mmol) of caesium carbonate in 0.1 ml of water and 1 ml of dioxane was degassed with argon for 5 min and stirred in a closed tube at 100 C. for 18 h. The reaction mixture was concentrated and the residue was partitioned between ethyl acetate and water. The organic phase was separated off, washed with saturated aqueous sodium chloride solution, dried over sodium sulphate, filtered and concentrated. The residue was purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate, gradient 0% to 50%). This gave 60 mg of the target product (64% of theory). LC-MS (Method A): Rt=3.08 min; m/z=547.1 (M+H)+ 1H-NMR (400 MHz, CDCl3): delta [ppm]=0.95 (t, 3H), 1.42 (s, 9H), 1.43 (s, 3H), 1.60 (dd, 1H), 1.66 (s, 1H), 1.81 (dd, 1H), 2.73 (s, 3H), 3.38 (s, 3H), 3.75 (ddd, 2H), 4.45 (s, 2H), 4.57 (s, 1H), 5.33 (s, 2H), 6.86 (d, 1H), 6.93 (dd, 2H), 7.29-7.38 (m, 1H), 9.03 (d, 1H).

Reference： [1]Patent: US2017/50961,2017,A1 .Location in patent: Paragraph 0855; 0856; 0857; 0858

41
[ 910251-11-5 ]
ethyl (R)-11-chloro-12-(3-hydroxy-3-methylbut-1-yn-1-yl)-3,3-dimethyl-8-oxo-2,3,8,13b-tetrahydro-1H-pyrido[2,1-a]pyrrolo[1,2-c]phthalazine-7-carboxylate [ No CAS ]
[ 76-05-1 ]
(R)-12-(3-hydroxy-3-methylbut-1-yn-1-yl)-11-(methoxymethyl)-3,3-dimethyl-8-oxo-2,3,8,13b-tetrahydro-1H-pyrido[2,1-a]pyrrolo[1,2-c]phthalazine-7-carboxylic acid trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Ethyl (R)-l l-chloro-12-(3-hydroxy-3-methylbut-l-yn-l-yl)-3,3- dimethyl-8-oxo-2,3,8,13b-tetrahydro-lH-pyrido[2,l-a]pyrrolo[l,2-c]phthalazine-7-carboxylate (53 mg, 0.093 mmol) was combined with trifluoro(methoxymethyl)-borane, potassium salt (40 mg, 0.26 mmol), Ruphos Pd G2 (5.1 mg, 0.007 mmol), and potassium carbonate (52 mg, 0.37 mmol) in dioxane:water (5: 1, ImL) under argon in a sealed vial. The mixture was stirred at 110 C for 2.5 hours, after which time it was cooled to 50 C and 1M lithium hydroxide (0.19 ml) was added. The mixture was stirred for 90 minutes, then cooled to room temperature, diluted with TFA and acetonitrile, and purified by preparative HPLC to provide (R)-12-(3-hydroxy-3- methylbut- 1 -yn-1 -yl)- 11 -(methoxymethyl)-3,3-dimethyl-8-oxo-2,3,8, 13b-tetrahydro- 1H- pyrido[2,l-a]pyrrolo[l,2-c]phthalazine-7-carboxylic acid as a TFA salt. XH NMR (400 MHz, Acetonitrile-d3) delta 8.47 (s, 1H), 8.01 (s, 1H), 7.50 (d, J = 1.1 Hz, 1H), 7.29 (s, 1H), 4.88 (d, J = 5.9 Hz, 1H), 4.62 (t, J = 0.8 Hz, 2H), 3.47 (s, 3H), 2.60 - 2.43 (m, 2H), 1.94 - 1.86 (m, 1H), 1.67 - 1.60 (m, 1H), 1.58 (s, 6H), 1.37 (s, 3H), 0.63 (s, 3H). iyF NMR (376 MHz, Acetonitrile- d3) delta -77.28 . MS (m/z) 437.2 [M+H]+.

Reference： [1]Patent: WO2018/144605,2018,A1 .Location in patent: Page/Page column 148; 149

42
[ 910251-11-5 ]
ethyl 12-(benzyloxy)-11-chloro-3,3-dimethyl-8-oxo-2,3,8,13b-tetrahydro-1H-pyrido[2,1-a]pyrrolo[1,2-c]phthalazine-7-carboxylate [ No CAS ]
ethyl 12-(benzyloxy)-11-(methoxymethyl)-3,3-dimethyl-8-oxo-2,3,8,13b-tetrahydro-1H-pyrido[2,1-a]pyrrolo[1,2-c]phthalazine-7-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With methanesulfonato(2-dicyclohexylphosphino-2?,6?-di-i-propoxy-1,1?-biphenyl)(2?-methylamino-1,1?-biphenyl-2-yl)palladium(II); caesium carbonate; ruphos; In water; toluene; at 110℃; for 1.5h;Inert atmosphere; Sealed tube;	Ethyl 12-(benzyloxy)- l l-chloro-3,3-dimethyl-8-oxo-2,3,8,13b-tetrahydro-lH-pyrido[2,l-a]pyrrolo[l,2-c]phthalazine- 7-carboxylate (737 mg, 1.54 mmol) was combined with trifluoro(methoxymethyl)-borane, potassium salt (701 mg, 4.62 mmol), Pd RuPhos G3 (154 mg, 0.185 mmol), RuPhos (129 mg, 0.28 mmol), and cesium carbonate (2.51 g, 7.69 mmol) in toluene:water (3: 1, 10 mL) under argon in a sealed vial. The mixture was heated at 110 C for 90 minutes with vigorous stirring, then cooled to room temperature, the aqueous layer was removed, and the organics were concentrated in vacuo and purified by flash column chromatography (hexanes / ethyl acetate / ethanol / triethylamine) to provide ethyl 12-(benzyloxy)-l l-(methoxymethyl)-3,3-dimethyl-8- oxo-2,3, 8, 13b-tetrahydro-lH-pyrido[2,l-a]pyrrolo[l,2-c]phthalazine-7-carboxylate. 'H NMR (400 MHz, Chloroform-d) delta 8.27 (s, 1H), 7.84 (s, 1H), 7.45 - 7.30 (m, 5H), 7.00 (s, 1H), 6.75 (s, 1H), 5.24 - 5.08 (m, 2H), 4.77 - 4.68 (m, 1H), 4.60 - 4.47 (m, 2H), 4.38 (q, J = 7.1 Hz, 2H), 3.51 (s, OH), 3.50 - 3.44 (m, 3H), 2.47 - 2.32 (m, 1H), 2.25 (t, J = 10.3 Hz, 1H), 1.79 (dd, J = 11.7, 8.9 Hz, 1H), 1.54 - 1.45 (m, 1H), 1.39 (t, J = 7.1 Hz, 3H), 1.32 (s, 3H), 0.67 (s, 3H). MS (m/z) 489.5 [M+H]+.

Reference： [1]Patent: WO2018/144605,2018,A1 .Location in patent: Page/Page column 150; 151

43
[ 910251-11-5 ]
isopropyl (R)-12'-(benzyloxy)-11'-chloro-8'-oxo-1',2',8',13b'-tetrahydrospiro[cyclopropane-1,3'-pyrido[2,1-a]pyrrolo[1,2-c]phthalazine]-7'-carboxylate [ No CAS ]
isopropyl (R)-12'-(benzyloxy)-11'-(methoxymethyl)-8'-oxo-1',2',8',13b'-tetrahydrospiro[cyclopropane-1,3'-pyrido[2,1-a]pyrrolo[1,2-c]phthalazine]-7'-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With [methanesulfonato(2-dicyclohexylphosphino-2',6'-di-isopropoxy-1,1'-biphenyl)(2'-methylamino-1,1'-biphenyl-2-yl)palladium(II)]; caesium carbonate; ruphos; In water; toluene; at 110℃; for 0.75h;Inert atmosphere; Sealed tube;	Methyl (R)-12'-(benzyloxy)-H'-chloro-8'-oxo- ,2',8',13b'-tetrahydrospiro[cyclopropane-l,3'- pyrido[2,l-a]pyrrolo[l,2-c]phthalazine]-7'-carboxylate (234 mg, 0.51 mmol) was dissolved in isopropanol (10 mL) with 2 drops of acetic acid. The mixture was stirred at reflux for 2.5 hours, then cooled to room temperature to provide isopropyl (R)-12'-(benzyloxy)-H'-chloro-8'-oxo- ,2',8',13b'-tetrahydrospiro[cyclopropane-l,3'-pyrido[2,l-a]pyrrolo[l,2-c]phthalazine]-7'- carboxylate. MS (m/z) 491.3 [M+H]+. The crude ester was combined with (0993) trifluoro(methoxymethyl)-borane, potassium salt (230 mg, 1.52 mmol), Pd RuPhos G4 (52 mg, 0.061 mmol), RuPhos (42 mg, 0.091 mmol), and cesium carbonate (823 mg, 2.53 mmol) in toluene:water (3: 1, 5 mL) under argon in a sealed vial. The mixture was heated at 110 C for 45 minutes with vigorous stirring, then cooled to room temperature, the aqueous layer was removed, and the organics were concentrated in vacuo and purified by flash column (0994) chromatography (hexanes / ethyl acetate / ethanol / triethylamine) to provide isopropyl (R)-12'- (benzyloxy)-i -(methoxymethyl)-8'-oxo- ,2',8',13b'-tetrahydrospiro[cyclopropane-l,3'- pyrido[2,l-a]pyrrolo[l,2-c]phthalazine]-7'-carboxylate. MS (m/z) 501.4 [M+H]+.

Reference： [1]Patent: WO2018/144605,2018,A1 .Location in patent: Page/Page column 173

44
[ 910251-11-5 ]
C₂₆H₂₄ClN₃O₄ [ No CAS ]
C₂₈H₂₉N₃O₅ [ No CAS ]

Reference： [1]Patent: WO2018/144605,2018,A1 .Location in patent: Page/Page column 191

45
[ 910251-11-5 ]
tert-butyl 4-(5-bromo-3-nitropyridin-2-yl)piperazine-1-carboxylate [ No CAS ]
tert-butyl 4-(5-(methoxymethyl)-3-nitropyridin-2-yl)piperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20.2%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In 1,4-dioxane; water; at 100℃; for 16h;	[0198] 7erf~butyl 4-(5-bromo-3-nitropyridin-2-yl)piperazine-l-carboxylate (5.28 g, 13.64 mmol), <strong>[910251-11-5]potassium trifluoro(methoxymethyl)borate</strong> (4.146 g, 27.3 mmol), PdCh(dppf) (1.996 g, 2.73 mmol) and CS2CQ3 (22.22 g, 68.2 mmol) were combined in dioxane (68.2 mL) and water (28 mL). The reaction mixture was heated at 100C for 16 hours, then cooled to RT, poured into brine (141 mL) and extracted with EtOAc (2 x 94 mL). The organic layers were combined, concentrated, and purified by flash column chromatography (silica gel column) eluting with a gradient of 10-40% EtOAc in heptane to give the title compound as a yellow oil (969 mg, 20,2%), f t NMR (500 MHz, DMSO-afe) 0 ppm 1.41 (s, 9 H), 3,28 (s, 3 H), 3.35 - 3.37 (m, 4 H), 3.43 - 3,46 (m, 4 H), 4.40 (s, 2 H), 8.22 (d, J=1.95 Hz, 1H), 8.40 (d, J=1.95 Hz, 1H); ESI-MS m/z [M i l l 353.3.

Reference： [1]Patent: WO2018/183145,2018,A1 .Location in patent: Paragraph 0198

46
[ 910251-11-5 ]
[ 766-51-8 ]
[ 21998-86-7 ]

Reference： [1]Chemistry - A European Journal,2019,vol. 25,p. 2199 - 2202

47
[ 910251-11-5 ]
rac-1-((1R,2R)-7-bromo-2-hydroxy-4,4-dimethyl-1,2,3,4-tetrahydronaphthalen-1-yl)-3-(5-methyl-2-(tetrahydro-2H-pyran-4-yl)pyridin-3-yl)urea [ No CAS ]
rac-1-((1R,2R)-2-hydroxy-7-(methoxymethyl)-4,4-dimethyl-1,2,3,4-tetrahydronaphthalen-1-yl)-3-(5-methyl-2-(tetrahydro-2H-pyran-4-yl)pyridin-3-yl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
12 mg	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; ruphos; In 1,4-dioxane; water; at 110℃; for 15h;Inert atmosphere;	Example 33 Synthesis of rac-1-((1R,2R)-2-hydroxy-7-(methoxy methyl)-4,4-dimethyl-1,2,3,4-tetrahydronaphthalen-1-yl)-3-(5-methyl-2-(tetrahydro-2H-pyran-4-yl)pyridin-3-yl)urea A crude product (82 mg) of rac-1-((1R,2R)-7-bromo-2-hydroxy-4,4-dimethyl-1,2,3,4-tetrahydronaphthalen-1-yl)-3-(5-methyl-2-(tetrahydro-2H-pyran-4-yl)pyridin-3-yl)urea was obtained from the compound (63 mg) obtained in (Example 26) <Step 3> and the compound (50 mg) obtained in (Example 32) <Step 2> in the same method as in (Example 2) <Step 3>. Tris(dibenzylideneacetone)dipalladium (0) (34 mg), 2-dicyclohexylphosphino-2',6'-diisopropoxy-1,1'-biphenyl (35 mg), potassium (methoxymethyl) trifluoroborate (0.14 g), cesium carbonate (0.24 g), 1,4-dioxane (1.0 mL), and water (0.25 mL) were added to this crude product (82 mg), and after purging with nitrogen by degassing under reduced pressure, the mixture was stirred at 110 C. for 15 hours. The reaction solution was filtered, and the filtrate was purified by preparative LC-Mass to obtain the title compound (12 mg).

Reference： [1]Patent: US2019/23657,2019,A1 .Location in patent: Paragraph 0873

48
[ 910251-11-5 ]
4-[[2-(3-bromophenyl)acetyl]amino]-N-tert-butylpyridine-2-carboxamide [ No CAS ]
N-tert-butyl-4-[[2-[3-(methoxymethyl)phenyl]acetyl]amino]pyridine-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In tetrahydrofuran; water; at 80℃; for 16h;Inert atmosphere;	A vessel was charged with 4-[[2-(3-bromophenyl)acetyljaminoj-N-tert-butyl-pyridine-2- carboxamide (Example 54 step 1)(50 mg, 0.13 mmol) PdCl2dppf (3 mg), <strong>[910251-11-5]potassium trifluoro(methoxymethyl)boranuide</strong> (0.45 mL, 0.26 mmol) 2M aq. sodium carbonate (0.26mL, 0.51 mmol) and heated at8O Cfor 16 hours. The mixture was allowed to cool to room temperature, poured onto water (20 mL) and extracted into EtOAc (3 x 20 mL). The combined organic extracts were washed with brine (50 mL), dried over Na2504 and concentrated in vacuo. The residue was dissolved in DMSO:MeCN (800 p1, 1:1), filtered and purified by preparative HPLC (acidic pH, early elution method) to afford the titledcompound as an off-white solid.1H NMR (500 MHz, DMSO-d6) O 10.76 (5, 1H), 8.44 (d, J = 5.5 Hz, 1H), 8.18 (d, J = 2.1Hz, 1H), 8.02 (5, 1H), 7.81 (dd, J = 5.5, 2.2 Hz, 1H), 7.34-7.27 (m, 2H), 7.25 (d, J = 7.7Hz, 1H), 7.20 (d, J = 7.5 Hz, 1H), 4.40 (5, 2H), 3.71 (5, 2H), 3.29 (5, 3H), 1.39 (5, 9H).

Reference： [1]Patent: WO2019/145726,2019,A1 .Location in patent: Page/Page column 271; 272

49
[ 910251-11-5 ]
(R)-7-chloro-3-isopropyl-8-(3-methoxypropoxy)-3,4-dihydrobenzo[b]oxepin-5(2H)-one [ No CAS ]
(R)-3-isopropyl-7-(methoxymethyl)-8-(3-methoxypropoxy)-3,4-dihydrobenzo[b]oxepin-5(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%	With tris-(dibenzylideneacetone)dipalladium(0); sodium carbonate; ruphos; In 1,4-dioxane; water; at 120℃; for 16h;Inert atmosphere;	To a mixture of (3R)-7-chloro-3-isopropyl-8-(3-methoxypropoxy)-3,4-dihydro-2H-1-benzoxepin-5-one (2.1 g, 6.4 mmol) and <strong>[910251-11-5]potassium trifluoro(methoxymethyl)borate</strong> (1.46 g, 9.64 mmol) in l,4-dioxane:water (10: 1, 22 mL) was added RuPhos (1.20 g, 2.57 mmol), tris(dibenzylideneacetone)dipalladium(0) (1.18 g, 1.29 mmol) and sodium carbonate (1.70 g, 16 mmol) in one portion under nitrogen. The mixture was stirred at 120 C for 16 h. The mixture was cooled to rt, H2O (30 mL) was added and the aqueous phase was extracted with EtOAc (2 x 20 mL). The combined organic phase was washed with saturated aqueous brine solution (30 mL), dried with anhydrous sodium sulfate, filtered and concentrated in vacuum. The residue was purified by normal phase SiO2 chromatography (0-15% EtO Ac/petroleum ether) to give (R)-3-isopropyl-7-(methoxymethyl)-8-(3-methoxypropoxy)-3,4-dihydrobenzo[b]oxepin-5(2H)-one as a yellow oil (0.7 g, 32% yield, m/z: 337 [M+H] observed).

Reference： [1]Patent: WO2019/177937,2019,A1 .Location in patent: Page/Page column 162

50
[ 910251-11-5 ]
5-[3-(benzyloxy)-7-bromo-1-fluoronaphthalen-2-yl]-1λ⁶,2,5-thiadiazolidine-1,1,3-trione [ No CAS ]
5-[3-(benzyloxy)-1-fluoro-7-(methoxymethyl)naphthalen-2-yl]-1λ⁶,2,5-thiadiazolidine-1,1,3-trione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With (1,2-dimethoxyethane)dichloronickel(II); Ir(dF(CF3)ppy)2(bpy)PF6; caesium carbonate; 4,4'-di-tert-butyl-2,2'-bipyridine; In 1,4-dioxane; N,N-dimethyl acetamide;Irradiation;	In a 4 mL vial were combined NiCl2 dimethoxyethane adduct (3.4 mg, 0.015 mmol, 0.12 equivalents) and 4,4'-di-ter/-butyl-2,2'-dipyridyl (4.15 mg, 0.015 mmol, 0.12 equivalents) in /V,/V-di methyl acetamide (1.0 mL). Example 1G (60 mg, 0.13 mmol, 1.0 equivalents), <strong>[910251-11-5]potassium trifluoro(methoxymethyl)borate</strong> (58 mg, 0.39 mmol, 3.0 equivalents), cesium carbonate (105 mg, 0.32 mmol, 2.5 equivalents) and bis[3,5-difluoro-2-[5-(trifluoromethyl)-2- pyridyl] phenyl] iridium(l+); 2-(2-pyridyl)pyridine; hexafluorophosphate (4.3 mg, 0.004 mmol, 0.03 equivalents) were added, followed by dioxane (1.0 mL). The reaction was irradiated overnight using a 450 nm LED photoreactor. The reaction was filtered and purified by reverse-phase preparative HPLC on a Waters XBridge C8 5 pm column (75 mm x 30 mm). A gradient of methanol (A) and 25 mM ammonium bicarbonate buffer (pH 10) in water (B) was used, at a flow rate of 40 mL/minute (0- 0.5 minutes 15% A, 0.5-8.0 minutes linear gradient 15-100% A, 8.0-9.0 minutes 100% A, 9.0- 9.1 minutes linear gradient 100-15% A, 9.1-10.0 minutes 15% A) to afford 5-[3-(benzyloxy)-l- fluoio-7-(methoxymethyl)naphthalen-2-yl]- 1 / 2,5-thiadiazolidinc- 1, 1,3-trione (52.4 mg, 94% yield).

Reference： [1]Patent: WO2019/246513,2019,A1 .Location in patent: Page/Page column 243; 244

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