[ CAS No. 1150114-80-9 ] {[proInfo.proName]}

Name: 1150114-80-9|1-Methyl-1H-indazole-6-boronic Acid|95%
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SKU: A734036
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Quality Control of [ 1150114-80-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1150114-80-9 ]

Product Details of [ 1150114-80-9 ]

CAS No. :	1150114-80-9	MDL No. :	MFCD09870053
Formula :	C₈H₉BN₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	175.98	Pubchem ID :	-
Synonyms :

Calculated chemistry of [ 1150114-80-9 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.12
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	50.82
TPSA :	58.28 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.04 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	0.47
Log Po/w (WLOGP) :	-0.75
Log Po/w (MLOGP) :	-0.28
Log Po/w (SILICOS-IT) :	-1.2
Consensus Log Po/w :	-0.35

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.67
Solubility :	3.73 mg/ml ; 0.0212 mol/l
Class :	Very soluble
Log S (Ali) :	-1.26
Solubility :	9.61 mg/ml ; 0.0546 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.36
Solubility :	7.66 mg/ml ; 0.0436 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.9

Safety of [ 1150114-80-9 ]

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 [ 1150114-80-9 ]

* 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 [ 1150114-80-9 ]

[ 1150114-80-9 ] Synthesis Path-Downstream 1~52

1
[ 32084-59-6 ]
[ 1150114-80-9 ]
[ 1327160-11-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 3152 - 3158

2
[ 32084-59-6 ]
[ 1150114-80-9 ]
[ 1327166-33-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 3152 - 3158

3
[ 1150114-80-9 ]
[ 1367874-63-2 ]
[ 1367875-46-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium acetate; sodium carbonate;di-tert-butyl[dichloro({di-tert-butyl[4-(dimethylamino)phenyl]phosphaniumyl})palladio][4-(dimethylamino)phenyl]phosphanium; In water; acetonitrile; at 150℃; for 0.666667h;Inert atmosphere; Microwave irradiation;	Example 136-( 1 -Methyl- 1 H-indazol-6-yl)-4-(tetrahydro-2H-pyran-4-yloxy)-1H-pyrazolo[4, 3-c]pyridineStep 13-( 1 -Methyl- 1 H-indazol-6-yl)-4-(tetrahydro-2H-pyran-4-yloxy)-1-trityl- 1 H-pyrazolo[4, 3-c]pyridine 3-iodo-4-(tetrahydro-2/-/-pyran-4-yloxy)-1-trityl-1H-pyrazolo[4,3-c]pyridine (100 mg, 0.170 mmol), 1-methyl-1/-/-indazol-6-ylboronic acid (42 mg, 0.238 mmol), bis(di-ferf-butyl(4- dimethylaminophenyI)phosphine) dichloropalladium (12 mg, 0.017 mmol), potassium acetate (23.4 mg, 0.238 mmol) and sodium carbonate (25.2 mg, 0.238 mmol) were charged into a microwave vial equipped with a stir bar. Acetonitrie (1.6 mL) and degassed water (0.6 mL) were then added and the reaction mixture was degassed with nitrogen for 5 min and then heated to 150 C under microwave irradiation for 40 min. The crude mixture was filtered through Celite, and concentrated to give the title compound.

Reference： [1]Patent: WO2012/38743,2012,A1 .Location in patent: Page/Page column 183

4
[ 1268867-67-9 ]
[ 1150114-80-9 ]
[ 1268864-64-7 ]

Reference： [1]Patent: WO2012/119046,2012,A2

5
[ 1268867-67-9 ]
[ 1150114-80-9 ]
[ 1396749-96-4 ]

Yield	Reaction Conditions	Operation in experiment
29%	With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; at 90℃; for 0.333333h;Inert atmosphere;	Step 1. Methyl 3-(isopropyl(methyl)amino)-2-(l-methyl-7H-indazol-6-yl)quinoxaline-6- carboxylateTo a solution of methyl 2-chloro-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate (Scheme I, 180.0 mg, 0.61 mmol) in dioxane (1 mL) was added l-methyl-iH-indazol-6- ylboronic acid (276.0 mg, 1.57 mmol), K3P04 (391.2 mg, 1.85 mmol), and Pd(PPh3)4 (35.0 mg, 0.03 mmol) under nitrogen atmosphere. After stirring 20 min at 90C, the reaction mixture was dissolved in dichloromethane (30 mL), washed with water (3 x 20 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford a residue, which was purified by a silica gel column with 0.05% - 0.2% ethyl acetate in petroleum ether to afford methyl 3-(isopropyl(methyl)amino)-2-(l-methyl-7H-indazol-6- yl)quinoxaline-6-carboxylate as a light yellow solid (70 mg, 29%).LC/MS (ES, m/z): [M+H]+ 390.0*H-NMR (300 MHz, CDC13) delta 8.55 (d, J = 2.4 Hz, 1H), 7.99 - 8.09 (m, 4H), 7.82 - 7.85 (m, 1H), 7.65 - 7.68 (m, 1H), 4.25 - 4.32 (m, 1H), 4.18 (s, 3H), 4.01 (s, 3H), 2.77 (s, 3H), 1.08 (d, 7 = 6.6 Hz, 6H)

Reference： [1]Patent: WO2012/119046,2012,A2 .Location in patent: Page/Page column 44

6
[ 1150114-80-9 ]
[ 1314883-33-4 ]
[ 1416315-08-6 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 11022 - 11030

7
[ 1170193-16-4 ]
[ 1150114-80-9 ]
[ 1435103-12-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 2111 - 2116

8
[ 1150114-80-9 ]
(S)-methyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-chloropyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate [ No CAS ]
[ 1471249-95-2 ]

Yield	Reaction Conditions	Operation in experiment
		Preparation of (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-(1-methyl-1H-indazol-6-yl)pyridin-4-yl)benzo[d]thiazol-6-yl)acetic acid: The reaction mixture of (S)-methyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-chloropyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate (20 mg, 0.039 mmol), <strong>[1150114-80-9]1-methyl-1H-indazole-6-boronic acid</strong> (10.3 mg, 0.058 mmol), 2N K2CO3 (100 muL, 0.19 mmol), Pd(PPh3)4 (4.3 mg, 0.004 mmol) in dioxane (1.5 mL) in sealed tube was heated at 110 C. for 2 h. After the starting material consumed, the reaction was cooled down, to the mixture was added MeOH, excess NaOH, the reaction mixture was heated at 45 C. overnight. Then the reaction mixture was neutralized by acetic acid, concentrated down, then treated by MeOH, and purified by reverse phase HPLC, eluting by 0-100% acetonitrile in H2O with 0.1% TFA to give the product. LCMS-ESI+: calc'd for C33H29ClN4O3S: 597.2 (M+H+). Found: 597.2 (M+H+). 1H NMR (400 MHz, CD3OD): delta 8.78 (d, J=2.6 Hz, 1H), 8.60 (s, 1H), 8.26 (s, 1H), 8.06 (s, 1H), 8.03-7.82 (m, 4H), 7.71-7.69 (m, 1H), 7.61-7.60 (m, 3H), 5.28 (s, 1H), 4.16 (s, 3H), 2.64 (s, 3H), 0.98 (s, 9H).

Reference： [1]Patent: US2013/281433,2013,A1 .Location in patent: Paragraph 0843

9
20-acetyl-7-chlorocamptothecin [ No CAS ]
[ 1150114-80-9 ]
[ 1579279-87-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	With tetrakis(triphenylphosphine) palladium(0); cesium fluoride; In 1,4-dioxane; at 120℃; for 0.5h;Inert atmosphere; Microwave irradiation;	General procedure: Compound 7(1eq), 8c (1.5eq), Pd(PPh3)4 (0.1eq) and CsF (2eq) were dissolvedin dioxane (5 mL) in a microwave vial under nitrogen atmosphere and thereaction mixture was irradiated in a microwave apparatus at 120 C for 30 min.After the reaction mixture was cooled to ambient temperature, the crude mixturewas purified by silica gel column chromatography (chloroform: acetone = 30: 1) to afford 9a-g.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 1597 - 1599

10
[ 1150114-80-9 ]
tert-butyl (2-(((3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)methyl)(methyl)amino)ethyl)carbamate [ No CAS ]
tert-butyl N-[2-(methyl((3-(1-methyl-1H-indazol-6-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)methyl)amino)ethyl]carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%	With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,2-dimethoxyethane; at 95℃;Inert atmosphere;	A mixture of tert-butyl N-[2-([[3-iodo-1-(oxan-2-yl)-1H-pyrazol-4-yl]methyl](methyl)amino)ethyl]carbamate (200 mg, 0.43 mmol, 1.00 equiv), K3PO4 (273 mg, 1.29 mmol, 3.00 equiv), <strong>[1150114-80-9](1-methyl-1H-indazol-6-yl)boronic acid</strong> (113 mg, 0.64 mmol, 1.50 equiv) and Pd(dppf)Cl2.CH2Cl2 (70 mg, 0.10 mmol, 0.20 equiv) in ethylene glycol dimethyl ether (20 mL) was stirred under nitrogen at 95 C. overnight. The resulting mixture was cooled to room temperature then concentrated under vacuum. The crude product was purified by Pre-HPLC with the following conditions (1-Pre-HPLC-005 (Waters)): Column, XBridge Shield RP18 OBD Column, 5 m, 19×150 mm; mobile phase, water with 10 mmol NH4HCO3 and CH3CN (18% CH3CN up to 58% in 10 min, up to 95% in 1 min, down to 18% in 2 min); Detector, UV 254/220 nm to yield 50 mg (25%) of tert-butyl 2-(methyl((3-(1-methyl-1H-indazol-6-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)methyl)amino)ethylcarbamate as a colorless oil. LCMS (method A, ESI): RT=1.16 min, m/z=469.0 [M+H]+.

Reference： [1]Patent: US2014/288105,2014,A1 .Location in patent: Paragraph 0206-0207

11
[ 1150114-80-9 ]
(S)-methyl 1-(3-fluoro-2-methylphenyl)-3-(((trifluoromethyl)sulfonyl)oxy)cyclopent-2-enecarboxylate [ No CAS ]
(S)-methyl 1-(3-fluoro-2-methylphenyl)-3-(1-methyl-1H-indazol-6-yl)cyclopent-2-enecarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
176 mg	With tetrakis(triphenylphosphine) palladium(0); cesium fluoride; In methanol; 1,2-dimethoxyethane; at 120℃; for 2h;Sealed tube; Microwave irradiation;	Step 1: (^-methyl l-(3-fluoro-2-methylphenyl)-3-(l-methyl-lH-indazol-6-yl)cyclopent- 2-enecarboxylate [00283] (^-Methyl l-(3-fluoro-2-methylphenyl)-3- (((trifluoromethyl)sulfonyl)oxy)cyclopent-2-enecarboxylate (300 mg, 0.79 mmol), (1- methyl-lH-indazol-6-yl)boronic acid (139 mg, 0.79 mmol), CsF (200 mg), DME (15 mL), MeOH (3 mL) and palladium tetrakis(triphenylphosphine) (20 mg) were combined in a sealed tube and heated by microwave to 120 C for 2 h. The reaction mixture was then evaporated to dryness onto silica and purified by flash chromatography (gradient elution, 0-100% EtOAc in so-hexane) to give the title compound as a colorless gum (176 mg).

Reference： [1]Patent: WO2014/159218,2014,A1 .Location in patent: Paragraph 00283

12
[ 1150114-80-9 ]
methyl 3'-fluoro-2'-methyl-4-(((trifluoromethyl)sulfonyl)oxy)-1,2,3,6-tetrahydro-[1,1'-biphenyl]-1-carboxylate [ No CAS ]
methyl 3'-fluoro-2'-methyl-4-(1-methyl-1H-indazol-6-yl)-1,2,3,6-tetrahydro-[1,1'-biphenyl]-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate; In 1,2-dimethoxyethane; at 85℃; for 24h;Inert atmosphere; Sealed tube;	Step 1 : methyl 3'-fluoro-2'-methyl-4-(1 -methyl-1 H-indazol-6-yl)-1 , 2,3, 6-tetrahydro- [1 ,1 '-biphenyl]-1 -carboxylate [00379] To a solution of methyl 3'-fluoro-2'-methyl-4- (((trifluoromethyl)sulfonyl)oxy)-1 ,2,3,6-tetrahydro-[1 , 1 '-biphenyl]-1 -carboxylate (600 mg, 1 .51 mmol) in dry DME (8 mL) in a reaction tube was added 1 -methyl- 1 H-indazol-6-yl boronic acid (270 mg, 1 .51 mmol) and Cs2CO3 (1 .48 g, 4.55 mmol). The resulting mixture was degased with nitrogen bubbling for 5 min. Pd(dppf)CI2.CHCI3 (49 mg, 0.061 mmol) was added, the tube sealed and the reaction heated at 85 C for 24 h. The reaction was evaporated to dryness and partioned between water (25 mL) and EtOAc (2 x 25 mL). The organic layers were combined and condensed. The crude product was purified using a Biotage 25 g SNAP column eluting with 0-20% EtOAc in hexane to give the title compound as a colourless oil (500 mg, 88%).

Reference： [1]Patent: WO2014/159224,2014,A1 .Location in patent: Paragraph 00379

13
[ 1150114-80-9 ]
methyl 4-((N-(4-bromophenyl)morpholine-4-carboxamido)methyl)benzoate [ No CAS ]
methyl 4-((N-(4-(1-methyl-1H-indazol-6-yl)phenyl)morpholine-4-carboxamido)methyl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In 1,4-dioxane; water; at 80℃; for 16h;	(Formula 8-6: methyl 4-((N-(4-(1-methyl-1H-indazol-6-yl)phenyl)morpholine-4-carboxamido)methyl)benzoate)[436][437]Compound ofFormula 8-5(methyl 4-((N-(4-bromophenyl)morpholine-4-carboxamido)methyl)benzoate; 0.185 g, 0.427 mmol), 1-methyl-indazol-6-ylboronic acid (0.090 g, 0.512 mmol), and Pd(dppf)Cl2(0.035 g, 0.043 mmol) were dissolved in 1,4-dioxane (3 mL), and then sodium carbonate (0.181 g, 1.71 mmol) dissolved in water (1 mL) was added to the reaction solution and stirred at 80 for 16 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate and saturated sodium hydrogen carbonate aqueous solution and concentrated under reduced pressure, and then the residue was purified and concentrated by column chromatography (silica; ethyl acetate/hexane=30%) to give the desired compound ofFormula 8-6(0.112 g, 71%) in the form of a white solid.

Reference： [1]Patent: WO2014/178606,2014,A1 .Location in patent: Paragraph 435; 436; 437

14
[ 1150114-80-9 ]
methyl 4-(((3-bromophenyl)((4-nitrophenoxy)carbonyl)amino)methyl)benzoate [ No CAS ]
methyl 4-(((3-(1-methyl-1H-indazol-6-yl)phenyl)((4-nitrophenoxy)carbonyl)amino)methyl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In 1,2-dimethoxyethane; water; at 120℃; for 0.25h;Microwave irradiation;	(Formula 3-2:methyl 4-(((3-(1-methyl-1H-indazol-6-yl)phenyl)((4-nitrophenoxy)carbonyl)amino)methyl)benzoate)[282][283]Compound ofFormula 3-1(methyl 4-(((3-bromophenyl)((4-nitrophenoxy)carbonyl)amino)methyl)benzoate; 1.00 g, 2.06 mmol), <strong>[1150114-80-9]1-methyl-1H-indazol-6-ylboronic acid</strong> (0.435 g, 2.47 mmol), Pd(dppf)Cl2(0.168 g, 0.206 mmol), and sodium carbonate (0.693 g, 4.53 mmol) were mixed with dimethoxyethane (5 mL)/H2O (5 mL), heated at 120 for 15 minutes under microwave irradiation, and then the temperature was lowered to room temperature. Water was poured into the reaction mixture, and the organic layer was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride aqueous solution, dehydrated with anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified and concentrated by column chromatography (silica; ethyl acetate/hexane=30 %) to give the desired compound ofFormula 3-2(1.03 g, 93%) in the form of a white solid.

Reference： [1]Patent: WO2014/178606,2014,A1 .Location in patent: Paragraph 281; 282; 283

15
[ 1150114-80-9 ]
tert-butyl 4-(4-bromo-2,6-difluorobenzoyl)piperazine-1-carboxylate [ No CAS ]
tert-butyl 4-(2,6-difluoro-4-(1-methyl-1H-indazol-6-yl)benzoyl)piperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 130℃; for 0.5h;Inert atmosphere; Microwave irradiation;	tert-Butyl 4-(4-bromo-2,6-difluorobenzoyl)piperazine-l-carboxylate (383.2mg, 0.946 mmol), 1 -methyl- lH-indazol-6-ylboronic acid (166 mg, 0.946 mmol) and potassium phosphate (1.00 g, 4.73 mmol) were suspended in a nitrogen purged solution of Dioxane (6.0 ml) and Water (1.2 ml). The reaction mixture was further purged with nitrogen for 5 minutes. Palladium Tetrakis (109 mg, 0.095 mmol) was added and the reaction solution was purged with nitrogen for 5 more minutes. The mixture was subjected to microwave irradiation at 130 C for 30 minutes resulting in a yellow biphasic solution. The organic layer (top) was removed, filtered through celite and concentrated in vacuo to afford the crude product as a light red powder. The crude product was subjected to FCC (Biotage SNAP 25; Gradient Eluent: 0 - 20% MeOH in in EtOAc with 0.5% triethylamine over 15 CV). This afforded the title compound (327 mg, 76%) as a light beige powder. LC-MS (ES, m z): 421 [M+H]+

Reference： [1]Patent: WO2014/164749,2014,A1 .Location in patent: Page/Page column 299; 300

16
[ 1150114-80-9 ]
C₁₃H₂₅IO₂Si [ No CAS ]
C₂₁H₃₂N₂O₂Si [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 1022 - 1028

17
[ 1150114-80-9 ]
(6-(R)-(f-Fluoro-4-hydroxy-indan-1-yloxy)-benzofuran-3-yl)acetic acid methyl ester [ No CAS ]
(6-(R)-(7-fluoro-4-(1-methyl-1H-indazol-6-yloxy)-indan-1-yloxy)-benzofuran-3-yl)acetic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
245 mg	With pyridine; oxygen; copper diacetate; In tetrahydrofuran; dichloromethane; at 20℃; for 22h;	Step 1: (6-(R)-(7-Fluoro-4-(1-methyl-1H-indazol-6-yloxy)-indan-1-yloxy)benzofuran-3-yl)acetic acid methyl ester [0263] 250 mg (0.70 mmol) of (6-(R)-(7-fluoro-4-hydroxyindan-1-yloxy)benzofuran-3-yl)acetic acid methyl ester (Intermediate 4a), 130 mg (0.72 mmol) of copper(II) acetate and 500 mul (6.19 mmol) of pyridine are dissolved in 3.0 ml DCM. Mol sieve is added and the mixture is stirred for 5 min. Then the tube is sealed by a septum and 10 ml oxygen are purged through. A solution of 250 mg (1.42 mmol) of 1-methylindazol-6-boronic acid in 5.0 ml THF is added dropwise in 6 h. The reaction mixture is stirred at r.t. for 16 h. The reaction mixture is diluted with diethylether and filtered. The organic layer is washed with 1N aq. HCl, dried and the solvent is evaporated. The residue is purified by chromatography on silica gel (PE/EtOAc) to give the title compound. Yield: 245 mg; LC (method 3): tR=0.80 min; Mass spectrum (ESI+): m/z=487 [M+H]+. [0264] The title compound may also be obtained from (6-(R)-(7-fluoro-4-hydroxyindan-1-yloxy)benzofuran-3-yl)acetic acid methyl ester and 6-bromo-1-methylindazole with copper iodide, N,N-dimethylgylcine (for example as HCl salt), and cesium carbonate in 1,4-dioxane at 100 C.
245 mg	With pyridine; oxygen; copper diacetate; In tetrahydrofuran; dichloromethane; at 20℃; for 22h;Molecular sieve; Sealed tube;	General procedure: Step 1: (6-(R)-(7-Fluoro-4-(1 -methyl-1 H-indazol-6-yloxy)-indan-1-yloxy)-benzofuran-3-yl)-acetic acid methyl ester 250 mg (0.70 mmol) of (6-(R)-(7-fluoro-4-hydroxy-indan-1 -yloxy)-benzofuran-3-yl)- acetic acid methyl ester (Intermediate 4a), 130 mg (0.72 mmol) of copper(ll) acetate and 500 muIota (6.19 mmol) of pyridine are dissolved in 3.0 ml DCM. Mol sieve is added and the mixture is stirred for 5 min. Then the tube is sealed by a septum and 10 ml oxygen are purged through. A solution of 250 mg (1 .42 mmol) of 1 -methylindazol-6- boronic acid in 5.0 ml THF is added dropwise in 6 h. The reaction mixture is stirred at r.t. for 16h. The reaction mixture is diluted with diethylether and filtered. The organic layer is washed with 1 N aq. HCI, dried and the solvent is evaporated. The residue is purified by chromatography on silica gel (PE/EtOAc) to give the title compound.Yield: 245 mg; LC (method 3): tR= 0.80 min; Mass spectrum (EST): m/z = 487 [M+H]+.The title compound may also be obtained from (6-(R)-(7-fluoro-4-hydroxy-indan-1 - yloxy)-benzofuran-3-yl)-acetic acid methyl ester and 6-bromo-1 -methylindazole with copper iodide, Nu,Nu-dimethylgylcine (for example as HCI salt), and cesium carbonate in 1 ,4-dioxane at 100 C.

Reference： [1]Patent: US2015/87829,2015,A1 .Location in patent: Paragraph 0263; 0264
[2]Patent: WO2015/44073,2015,A1 .Location in patent: Page/Page column 69

18
[ 807325-83-3 ]
[ 1150114-80-9 ]
C₂₆H₂₃N₅O₂ [ No CAS ]