[ CAS No. 1256359-09-7 ] {[proInfo.proName]}

Name: 1256359-09-7|1-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole|97%
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SKU: A903812
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Quality Control of [ 1256359-09-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1256359-09-7 ]

SDS Specification

Alternatived Products of [ 1256359-09-7 ]

Product Details of [ 1256359-09-7 ]

CAS No. :	1256359-09-7	MDL No. :	MFCD15071439
Formula :	C₁₄H₁₉BN₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SHPRKJZVUGXCTM-UHFFFAOYSA-N
M.W :	258.12	Pubchem ID :	53216819
Synonyms :

Calculated chemistry of [ 1256359-09-7 ]

Physicochemical Properties

Num. heavy atoms :	19
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.5
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	77.47
TPSA :	36.28 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 :	No
Log Kp (skin permeation) :	-6.06 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	2.56
Log Po/w (WLOGP) :	1.87
Log Po/w (MLOGP) :	1.45
Log Po/w (SILICOS-IT) :	1.32
Consensus Log Po/w :	1.44

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.34
Solubility :	0.119 mg/ml ; 0.00046 mol/l
Class :	Soluble
Log S (Ali) :	-2.97
Solubility :	0.277 mg/ml ; 0.00107 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.08
Solubility :	0.0217 mg/ml ; 0.0000839 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.9

Safety of [ 1256359-09-7 ]

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

Application In Synthesis of [ 1256359-09-7 ]

* 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.

Upstream synthesis route of [ 1256359-09-7 ]
Downstream synthetic route of [ 1256359-09-7 ]

[ 1256359-09-7 ] Synthesis Path-Upstream 1~1

1
[ 590417-94-0 ]
[ 73183-34-3 ]
[ 1256359-09-7 ]

Yield	Reaction Conditions	Operation in experiment
70%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxaneReflux; Inert atmosphere	Compound numbers 1 to 11 recited in Example 16 apply only to Example 16. To a stirred suspension of 6-bromo-l -methyl- lH-indazole (1.0 g, 4.7 mmol) in 1,4-Dioxane (20 mL) was added 4,4,4',4',5,5,5',5'-octamethyl-2,2'- bi(l,3,2-dioxaborolane) (1.43 g, 5.64mmol), potassium acetate (0.69 g, 7.0 mmol), and [Ι,Γ- Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.17 g, 0.23 mmol), and the solution was then refluxed overnight under nitrogen. The solvent was then removed, and the product was obtained by flash chromatography with petroleum ether/ ethyl acetate=(10/l) as eluent (1.2 g, yield 70percent)

Reference： [1] Patent: WO2016/210296, 2016, A1, . Location in patent: Page/Page column 192; 193

[ 1256359-09-7 ] Synthesis Path-Downstream 1~12

1
[ 663948-23-0 ]
[ 1256359-09-7 ]
[ 76-05-1 ]
4-amino-8-(1-methyl-1H-indazol-6-yl)cinnoline-3-carboxamide trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
27%		EXAMPLE 1 : 4-amino-8-(l-methyl-lH-indazol-6-yl)cinnoline-3-carboxamide [0247] 4-Amino-8-bromocinnoline-3-carboxamide hydrochloride (0.090 g, 0.296 mmol), l-methyl-6-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-indazole (0.115 g, 0.445 mmol) and 2M Na2C03 (0.296 mL, 0.593 mmol) were suspended in dioxane. PdCl2(dppf) (0.022 g, 0.030 mmol) was added and the mixture was heated in a microwave reactor at 140C for 45 minutes. The reaction mixture was filtered and concentrated. The residue was taken up in MeOH (5 mL) and purified by preparative HPLC (Sunfire Prep 5 muiotaeta C 18, 75 x 30 mm column) eluting with a gradient of 15-40% ACN (containing 0.035% TFA) in water (containing 0.05% TFA). The pure fractions were collected, evaporated to a minimal volume, and lyophilized to give a TFA salt of the title compound (25 mg, 27%). 1H NMR (400 MHz, DMSO-de) delta ppm 4.09 (s, 3 H), 7.40 (dd, J=8.34, 1.01 Hz, 1 H), 7.77 - 7.93 (m, 3 H), 7.99 (dd, J=7.20, 1.14 Hz, 1 H), 8.14 (d, J=1.01 Hz, 1 H), 8.44 (br s, 1 H), 8.55 (d, J=8.59 Hz, 1 H); ESI-MS m/z [M+H]+ 319.2.

Reference： [1]Patent: WO2013/148603,2013,A1 .Location in patent: Paragraph 0246-0247

2
[ 1181329-13-4 ]
[ 1256359-09-7 ]
[ 1229207-16-2 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 3856 - 3873

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In dimethyl sulfoxide; at 80.0℃; for 6h;Inert atmosphere;	General procedure: To a solution of 4-bromo-N,N-2-trimethylaniline (571,7 mg, 2,67 mmol) in DMSO (20mL) was added KOAc (787 mg, 8.01 mmol), PdCl2(dppf) (293 mg, 0.4 mmol) and 4 ,4 ,4 ,4,5 ,5,5',5'-octamethyl-2,2'-b(1,3,2-dioxaborolane) (1.36 g, 5,34 mmol). Themixture was stirred at 80 C for 6 hours under N2. The reaction was added to 150 mLof water, extracted with EA, washed with brine, concentrated to give crude. The crude was purified by prep-TLC (EA:PE=1:5) to give white solid. MS (m/z): 262 (M +H ).

4
[ 1174429-23-2 ]
[ 1256359-09-7 ]
3-(1-methyl-1H-indazol-6-yl)-5-morpholino-4-oxa-1-thia-7-indenone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
6%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; at 90.0℃; for 2h;Inert atmosphere;	3-Bromo-5-morpholino-4-oxa-1thia-7indenone (Compound 126) (53 mg, 0.17 mmol), 4,4,5,5-tetramethyl-2-(1-methyl-1H-indazol-6yl)-1,3,2-dioxaborolane (87 mg, 0.34 mmol), were dissolved in toluene/EtOH (1.7 mL of a 2:1 v/v mixture) and treated with 2 M aqueous Na2CO3 (0.6 mL). The resulting mixture was degassed with nitrogen fiat 10 minutes. This was treated with Pd[Ph3P]4 (10 mg 8.4 mumol) and the resulting mixture was heated to 90 C. for 2 hours under a nitrogen atmosphere. The reaction mixture was cooled, diluted with ethyl acetate (20 mL) and filtered through a pad of Celite. The filtrate was washed with water (20 mL) and the organic phase was separated, dried (Na2SO4), filtered and concentrated in vacuo to yield the crude material. This was purified by preparative TLC plate eluting with ethyl acetate. The plate was run three times. 3-(1-Methyl-1H-indazol-6-yl)-5-morpholino-4-oxa-1-thia-7-indenone (Compound 130) was obtained as a white solid (4 mg, 0.01 mmol, 6%). HPLC (254 nm)-Rt 3.09 min. MS (ESI) m/z 368.3 [M+H]+ Purity=94.6% by UV (254 nm).

Reference： [1]Patent: US2015/344494,2015,A1 .Location in patent: Paragraph 0259

5
[ 1256359-09-7 ]
6-chloro-N-(4-chlorophenyl)-2-morpholinopyrimidin-4-amine [ No CAS ]
N-(4-chlorophenyl)-6-(1-methyl-1H-indazol-6-yl)-2-morpholinopyrimidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; at 90.0℃;Inert atmosphere;	General procedure: General Procedure for Suzuki Coupling[000171j To a mixture of an intermediate of formula 100(1 eq) or formula 102(1 eq), a0/RB . -boronic acid of formula R2B(OH)2 or boronate ester of formula 0 (1 eq) in 1,4 dioxane, 2 M solution of potassium phosphate was added and purged with argon for 15 mm followed by the addition of tetrakis triphenyl phosphine palladium (0.06 eq) and stirred at 90 C for overnight. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was filtered through celite and evaporated to dryness. The residue was taken in ethyl acetate, washed with water, brine, dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crude product was purified by column chromatography/preparative HPLC to afford the intermediate of formula 101 or a Compound of Formula I, respectively.:_[000 177j The title compound has been synthesized by following the General Procedure for Suzuki Coupling using compound 3 and Boronate ester 4 in Scheme 3.?H NMR (400 MHz, DMSO-d6) oe: 10.06 (s, 1H), 8.22 (s, 1H), 8.13 (s, 1H), 7.89 (d, J= 8.4 Hz, 1H), 7.75 - 7.65 (m, 3H), 7.41 (d, J= 8.4 Hz, 2H), 6.73 (s, 1H), 4.14 (s, 3H), 3.84 - 3.72 (m, 8H); HPLC purity: 99.45%; LCMS Calculated for C22H21C1N60 (free base): 420.15; Observed: 421.20 (M + 1).

Reference： [1]Patent: WO2016/57834,2016,A1 .Location in patent: Paragraph 000171; 000177

6
[ 590417-94-0 ]
[ 73183-34-3 ]
[ 1256359-09-7 ]

Yield	Reaction Conditions	Operation in experiment
70%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane;Reflux; Inert atmosphere;	Compound numbers 1 to 11 recited in Example 16 apply only to Example 16. To a stirred suspension of 6-bromo-l -methyl- lH-indazole (1.0 g, 4.7 mmol) in 1,4-Dioxane (20 mL) was added 4,4,4',4',5,5,5',5'-octamethyl-2,2'- bi(l,3,2-dioxaborolane) (1.43 g, 5.64mmol), potassium acetate (0.69 g, 7.0 mmol), and [Iota,Gamma- Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.17 g, 0.23 mmol), and the solution was then refluxed overnight under nitrogen. The solvent was then removed, and the product was obtained by flash chromatography with petroleum ether/ ethyl acetate=(10/l) as eluent (1.2 g, yield 70percent)

Reference： [1]Patent: WO2016/210296,2016,A1 .Location in patent: Page/Page column 192; 193

7
[ 1193-21-1 ]
[ 1256359-09-7 ]
6-(6-chloropyrimidin-4-yl)-1-methyl-1H-indazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; In water; acetonitrile;Reflux; Inert atmosphere;	To a stirred suspension of l-methyl-6-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan- 2-yl)-lH-indazole (1.2 g, 4.7 mmol) in acetonitrile (20 mL) and water (5mL) was added 4,6- dichloropyrimidine (0.7 g, 4.65 mmol), sodium bicarbonate (0.69 g,7.05mmol), and bis(triphenylphosphine)palladium(II) dichloride (0.016 g,0.0235 mmol), and then the solution was refluxed overnight under nitrogen. The solvent was then removed, and the product was obtained by flash chromatography with petroleum ether/ ethyl acetate=(3/l) as eluent (0.8 g, yield 70%)

Reference： [1]Patent: WO2016/210296,2016,A1 .Location in patent: Page/Page column 192; 193

8
[ 1256359-09-7 ]
N₁-(6-(1-methyl-1H-indazol-6-yl)pyrimidin-4-yl)benzene-1,3-diamine [ No CAS ]

Reference： [1]Patent: WO2016/210296,2016,A1

9
[ 1256359-09-7 ]
N-(3-((6-(1-methyl-1H-indazol-6-yl)pyrimidin-4-yl)amino)phenyl)-4-nitrobenzamide [ No CAS ]

Reference： [1]Patent: WO2016/210296,2016,A1

10
[ 1256359-09-7 ]
4-amino-N-(3-((6-(1-methyl-1H-indazol-6-yl)pyrimidin-4-yl)amino)phenyl)benzamide [ No CAS ]

Reference： [1]Patent: WO2016/210296,2016,A1

11
[ 1256359-09-7 ]
(E)-4-(4-(dimethylamino)but-2-enamido)-N-(3-((6-(1-methyl-1H-indazol-6-yl)pyrimidin-4-yl)amino)phenyl)benzamide [ No CAS ]

Reference： [1]Patent: WO2016/210296,2016,A1

12
[ 1256359-09-7 ]
tert-butyl N-[5-(4-acetylpiperazin-1-yl)-3-bromo-2-methylpyrazolo[1,5-a]pyrimidin-7-yl]-N-[3-(methanesulfonyl)phenyl]methyl carbamate [ No CAS ]
1-[4-(2-methyl-3-(1-methylindazol-6-yl)-7-[3-(methylsulfonyl)phenyl]methylamino}-pyrazolo[1,5-a]pyrimidin-5-yl)piperazin-1-yl] ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26%		To a solution of Intermediate 14 (400 mg, 0.64 mmol) in 1,4-dioxane (10 mL) were added 1 -methyl-6-(4,4,5 ,5 -tetramethyl- 1,3 ,2-dioxaborolan-2-yl)indazole (166 mg, 0.64 mmol) and 1M aqueous potassium phosphate tribasic solution (1.9 mL, 1.9 mmol). The mixture was purged with nitrogen for 15 minutes prior to addition of tetrakis(triphenylphosphine)palladium(0) (74.4 mg, 0.064 mmol). The mixture was heated at95C for 1 h, then cooled to ambient temperature and concentrated in vacuo. The residue was dry-loaded onto silica for purification by flash column chromatography on silica (gradient elution with 0-100% EtOAc/isohexane, followed by 0-20% MeOH in EtOAc). The resulting yellow gum was dissolved in DCM (10 mL) and MeOH (1 mL), then treated with 4M hydrogen chloride in 1,4-dioxane (10 mL). After 90 minutes, the mixture was concentrated in vacuo. The residue was purified using reverse phase silica flash chromatography (pH 10, gradient elution with 0-100% acetonitrile in water) to afford the title compound (101 mg, 26%) as a white solid. oH (300 MHz, DMSO-d6) 8.3 1-8.24 (m,1H), 8.11-8.07 (m, 1H), 7.98-7.94 (m, 2H), 7.86-7.78 (m, 2H), 7.73 (dd,J8.5, 0.8 Hz,1H), 7.68-7.60 (m, 1H), 7.57 (dd, J8.5, 1.3 Hz, 1H), 5.69 (s, 1H), 4.72 (d, J6.6 Hz, 2H),4.03 (s, 3H), 3.69-3.61 (m, 2H), 3.61-3.47 (m, 6H), 3.21 (s, 3H), 2.59 (s, 3H), 2.03 (s,3H). LCMS (ES+) [M+H] 573 RT 2.01 minutes (method 3).

Reference： [1]Patent: WO2017/55305,2017,A1 .Location in patent: Page/Page column 101; 102

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P502	Refer to manufacturer/supplier for information on recovery/recycling

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 1256359-09-7 ] {[proInfo.proName]}

Quality Control of [ 1256359-09-7 ]

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[ 1256359-09-7 ] Synthesis Path-Upstream 1~1

[ 1256359-09-7 ] Synthesis Path-Downstream 1~12

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Organoboron

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[ 1256359-09-7 ]

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[ 1256359-09-7 ]