[ CAS No. 1023595-17-6 ] {[proInfo.proName]}

Name: 1023595-17-6|(1H-Indazol-4-yl)boronic acid|97%
Brand: Ambeed
SKU: A103451
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Quality Control of [ 1023595-17-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1023595-17-6 ]

SDS Specification

Alternatived Products of [ 1023595-17-6 ]

Product Details of [ 1023595-17-6 ]

CAS No. :	1023595-17-6	MDL No. :	MFCD09878901
Formula :	C₇H₇BN₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BGZZJZIZRARGGZ-UHFFFAOYSA-N
M.W :	161.95	Pubchem ID :	44118310
Synonyms :

Calculated chemistry of [ 1023595-17-6 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	3.0
Molar Refractivity :	45.92
TPSA :	69.14 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) :	-6.96 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	0.46
Log Po/w (WLOGP) :	-0.76
Log Po/w (MLOGP) :	-0.61
Log Po/w (SILICOS-IT) :	-0.58
Consensus Log Po/w :	-0.3

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.62
Solubility :	3.86 mg/ml ; 0.0238 mol/l
Class :	Very soluble
Log S (Ali) :	-1.48
Solubility :	5.36 mg/ml ; 0.0331 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.79
Solubility :	2.62 mg/ml ; 0.0162 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.91

Safety of [ 1023595-17-6 ]

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 [ 1023595-17-6 ]

* 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 [ 1023595-17-6 ]

[ 1023595-17-6 ] Synthesis Path-Downstream 1~50

1
[ 1023595-17-6 ]
[ 76-05-1 ]
C₂HF₃O₂*C₂₀H₁₉N₇OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 201Preparation of: EPO <DP n="226"/>A mixture of 4-indazole-boronic acid (17 mg, 0.07 mmol), (24 mg, 0.05 mmol), Pd(Ph3P)4, K2co3 (22 mg) in a 3:1 mixture of dioxane/H2O (1 ml_) was heated at 150 0C for 30 minutes by microwave. The mixture was cooled, concentrated and then treated with a 9:1 mixture of TFA/hfeO at rt for 2h and then concentrated. The residue was taken up into 3:1 mixture of DMSO/CH3CN and purified by preparative LC to provide the title compound as TFA salt. HPLC-MS RT= 1.72 minutes, mass calculated for formula C20Hi9N7OS 405.14, observed LCMS m/z 406.15 (M+H).

Reference： [1]Patent: WO2008/54702,2008,A1 .Location in patent: Page/Page column 224-225

2
[ 1023595-17-6 ]
[ 1137278-38-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium acetate;trans-bis(triphenylphosphine)palladium dichloride; In water; acetonitrile; at 150℃; for 0.25h;Microwave irradiation;	Example 72; 4-(5-(lH-indazol-4-yl)-2-(methylthio)thiazolo[4,5-d]pyrimidin-7- yl)morpholine 147[00404] 5-Chloro-7-morpholino-2-(thiazol-4-yl)thiazolo[4,5-d]pyrimidine , lH-indazol-4- yl-4-boronic acid (2.5 eq), and trans-dichlorobis(triphenylphosphine)palladium(II) (0.1 eq) were <n="100"/>slurried with equal parts IM potassium acetate (3 eq) and acetonitrile. The solution was microwaved at 150 C for 15 minutes. The solution filtered and the solution was dried in vacuo. The resulting residue was purified by reverse phase silica gel chromatography to give the product 147.

Reference： [1]Patent: WO2009/42607,2009,A1 .Location in patent: Page/Page column 98-99

3
[ 1023595-17-6 ]
[ 1137278-66-0 ]
[ 1137278-15-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;trans-bis(triphenylphosphine)palladium dichloride; In water; acetonitrile; at 130℃; for 0.633333h;Microwave irradiation;	5-Chloro-2-((4-methylsulfonylpiperazin- 1 -yl)methyl)-7-moipholinothiazolo[5,4- d]pyrimidine, lH-indazol-4-yl-4-boronic acid (1.2 eq), and trans- dichlorobis(triphenylphosphine)palladium(II) (0.1 eq) were combined in a solution of equal parts sodium carbonate aqueous solution (IM, 3 eq) and acetonitrile. The solution was microwaved at 1300C for eighteen minutes. An additional 0.1 equivalents of trans- dichlorobis(triphenylphosphine)palladium(II) was added and the solution was microwaved at130 0C for an additional twenty minutes. Acetonitrile was added and the solution was filtered.The organic layer was purified by reverse phase chromatography to give the off white solid of129.

Reference： [1]Patent: WO2009/42607,2009,A1 .Location in patent: Page/Page column 91

4
[ 1023595-17-6 ]
[ 1137279-06-1 ]
[ 1137278-31-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;trans-bis(triphenylphosphine)palladium dichloride; In water; acetonitrile; at 140℃; for 0.166667h;Microwave irradiation;	(5-Chloro-7-morpholinothiazolo[4,5-d]pyrimidin-2-yl)(4- methylsulfonylpiperazin-l-yl)methanone, lH-indazol-4-yl-4-boronic acid (2.5 eq), and trans- dichlorobis(triphenylphosphine)palladium(II) (0.1 eq) were slurried with equal parts IM sodium carbonate aqueous solution (3 eq) and acetonitrile. The solution was microwaved at 140 C for 10 minutes. Water was added and the solution was filtered. The resulting precipitate was washed with methylene chloride and the organic layer was purified by silica gel chromatography followed by reverse phase silica gel chromatography to give the product 141.

Reference： [1]Patent: WO2009/42607,2009,A1 .Location in patent: Page/Page column 96

5
[ 1023595-17-6 ]
[ 1220700-80-0 ]
[ 1220700-95-7 ]

Yield	Reaction Conditions	Operation in experiment
99%	With potassium carbonate;bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; water; at 100℃; for 3h;Sealed tube;	Step i; A mixture of 57 (2.09 g, 5.00 mmol), 1 H-indazol-4-ylboronic acid (1.21 g, 7.50 mmol), Pd(PPh3^CI2 (213 mg, 0.30 mmol), and K2CO3 (2.07 g, 15.0 mmol) in dioxane/water (20/10 ml_) was bubbled with nitrogen for 5 minutes. The reaction mixture was then heated in a sealed tube at 100 C to give a brown solution, which turned to a gray suspension later. Heating was continued for 3 h. After cooling the mixture was diluted with water (50 ml_) and vigorously stirred. The solid was collected by vacuum-filtration and further dried to give 2.49 g (99%) of 89 as a yellow solid. 1H NMR (400 MHz, CDCI3) delta 1.48 (s, 9 H), 1.94 (d, J=6.32 Hz, 2 H), 2.84 (br s, 4 H), 3.63 (s, 3 H), 4.31 (br s, 2 H), 6.33 (br s, 1 H), 7.56 - 7.63 (m, 1 H), 7.64 - 7.70 (m, 1 H), 7.74 (d, J=7.07 Hz, 1 H), 8.12 (d, J=8.84 Hz, 1 H), 8.45 - 8.66 (m, 2 H), 8.78 (s, 1 H), 10.44 (br s, 1 H).

Reference： [1]Patent: WO2010/38165,2010,A1 .Location in patent: Page/Page column 107

6
[ 1023595-17-6 ]
[ 1220700-99-1 ]
[ 1220699-09-1 ]

Yield	Reaction Conditions	Operation in experiment
68%	With potassium carbonate;bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; water; at 90℃;Sealed tube;	Step 3; A mixture of 1 -(1-acetylpiperidin-4-yl)-8-chloro-3-methyl-1 /-/-imidazo[4,5- c][1 ,5]naphthyridin-2(3H)-one (93) (540 mg, 1.50 mmol), 1 H-indazol-4-ylboronic acid (364 mg, 2.25 mmol), Pd(PPh3)2CI2 (74.4 mg, 0.105 mmol), and K2CO3 (622 mg, 4.50 mmol) in dioxane/water (8/4 ml_) was bubbled with nitrogen for 5 minutes, and heated in a sealed tube at 90 C overnight. After cooling the reaction mixture was partitioned between water (40 ml_) and CH2CI2/MeOH (100/5 ml_). The aqueous layer was further extracted with CH2CI2 (50 ml_). The organic extract was washed with brine, dried over sodium sulfate, and concentrated to give a waxy, yellow solid, which was purified on ISCO purification system with a 40-gram column using 0 - 10% MeOH in CH2CI2 to afford 450 mg (68%) of the title compound 254 as a waxy, pale yellow solid. 1H NMR (400 MHz, CDCI3) delta 1.88 - 2.04 (m, 2 H), 2.08 (br s, 3 H), 2.62 (t, J=12.51 Hz, 1 H), 2.82 (br s, 1 H), 3.02 (br s, 1 H), 3.24 (t, J=12.25 Hz, 1 H), 3.64 (s, 3 H), 3.95 (d, J=13.14 Hz, 1 H), 4.85 (d, J=12.88 Hz, 1 H), 6.28 (br s, 1 H), 7.54 - 7.64 (m, 1 H), 7.70 (t, J=7.20 Hz, 2 H), 8.12 (d, J=8.84 Hz, 1 H), 8.56 (d, J=8.84 Hz, 2 H), 8.79 (s, 1 H), 11.02 (br s, 1 H).

Reference： [1]Patent: WO2010/38165,2010,A1 .Location in patent: Page/Page column 110

7
[ 1023595-17-6 ]
[ 1220113-84-7 ]
methyl 2-(1H-indazol-4-yl)-8-thiomethyl-4-morpholin-4-yl-pyrido[3,2-d]pyrimidine-6-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 90℃; for 12h;	Intermediate 22: Methyl 2-(1 H-lndazol-4-yl)-8-thiomethyl-4-morpholin-4-yl-pyridor3,2- dlpyrimidine-6-carboxylateA suspension of Example 2 (200 mg; 0.56 mmol), <strong>[1023595-17-6]indazole-4-boronic acid</strong> (180 mg; 1.12 mmol), Pd(PPh3)4 (64 mg; 0.06 mmol), sodium carbonate (170 mg; 1.6 mmol) in dioxane (12 ml.) and water (12 mL) was stirred at 900C for 12 hours, filtered through a short plug of Celite then concentrated in vacuo to afford the title compound as a yellow solid which was used without further purification. HPLC (Method C): RT 2.47 min (purity 68%). MS (ES+): 437.0.

Reference： [1]Patent: WO2010/37765,2010,A2 .Location in patent: Page/Page column 67-68

8
[ 1023595-17-6 ]
[ 1268849-99-5 ]
[ 1268850-20-9 ]

Yield	Reaction Conditions	Operation in experiment
19%	With PdPCy3; sodium carbonate; In 1,2-dimethoxyethane; water; at 150℃; for 0.5h;Inert atmosphere; Microwave irradiation;	General procedure: The chloropyrimidine (1.0 equiv), boronic acid or ester (2.2 equiv), Bedford catalyst 29 (0.05 equiv) and 2 M aqueous Na2CO3 (2.2 equiv) were dissolved in 1,2-DME. The solution was degassed and backfilled with nitrogen, then stirred with microwave heating at 150 C for 30 min. The reaction mixture was cooled, absorbed onto a plug of silica (100 mg) and eluted (CHCl3/MeOH, 9:1). The crude product was obtained by evaporating the filtrate in vacuo and purified by one of the following methods:Method A: The crude compound was dissolved in methanol and purified using an SCX-2 ion exchange column, eluting first with MeOH, then 2 M NH3 in MeOH.Method B: Purification by preparative TLC using the specified eluent.Method C: Recrystallisation from MeOH/CHCl3/hexane, 1:1:4.