[ CAS No. 1150271-42-3 ]

Name: 1150271-42-3|Methyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-7-carboxylate|98%
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SKU: A599840
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Quality Control of [ 1150271-42-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1150271-42-3 ]

SDS Specification

Alternatived Products of [ 1150271-42-3 ]

Product Details of [ 1150271-42-3 ]

CAS No. :	1150271-42-3	MDL No. :	MFCD11504970
Formula :	C₁₆H₂₀BNO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	301.15	Pubchem ID :	-
Synonyms :

Calculated chemistry of [ 1150271-42-3 ]

Physicochemical Properties

Num. heavy atoms :	22
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.44
Num. rotatable bonds :	3
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	86.05
TPSA :	60.55 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
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) :	2.92
Log Po/w (WLOGP) :	2.25
Log Po/w (MLOGP) :	1.31
Log Po/w (SILICOS-IT) :	2.36
Consensus Log Po/w :	1.77

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.65
Solubility :	0.0672 mg/ml ; 0.000223 mol/l
Class :	Soluble
Log S (Ali) :	-3.85
Solubility :	0.0423 mg/ml ; 0.00014 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.95
Solubility :	0.00339 mg/ml ; 0.0000113 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	3.07

Safety of [ 1150271-42-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1150271-42-3 ]

* 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 [ 1150271-42-3 ]

[ 1150271-42-3 ] Synthesis Path-Downstream 1~10

1
[ 1942055-10-8 ]
[ 1150271-42-3 ]
[ 1942056-81-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene In tetrahydrofuran at 70℃; for 3h; Inert atmosphere;	1.27.1 1.27.1 methyl 2-(6-(tert-butoxycarbonyl)-5-(1-((3-(2-((tertbutoxycarbonyl)(methyl)amino)ethoxy)-5,7-dimethyladamantan-1-yl)methyl)-5-methyl-1H-pyrazol-4-yl)pyridin-2-yl)-1H-indole-7-carboxylate To a stirred solution of methyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-7-carboxylate (370mg), tris(dibenzylideneacetone)dipalladium(0) (30 mg), 1,2,3,4,5-pentaphenyl-1′-(di-tert-butylphosphino)ferrocene (30 mg) and potassium phosphate (550 mg) in tetrahydrofuran (2 mL) was added Example 1.1.11(735 mg). The mixture was purged with nitrogen and stirred at 70° C. for 3 hours. The reaction was dilutedwith ethyl acetate and washed with water and brine. The aqueous layer was back extracted by ethyl acetate.The combined organic layers were dried over sodium sulfate, filtered and concentrated. The residue waspurified via silica gel chromatography, eluting with 0-20% ethyl acetate in heptanes, to give the titlecompound. MS (ESI) m/e 780.4 (M-H)-
	With potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene In tetrahydrofuran at 70℃; for 3h; Inert atmosphere;	1.1.27.1.27.1 1.27.1 methyl 2-(6-(tert-butoxycarbonyl)-5-(l-((3-(2-((tert- butoxycarbonyl)(methyl)amino)ethoxy)-5,7-dimethyladamantan-l- yl)methyl)-5-methyl-lH-pyrazol-4-yl)pyridin-2-yl)-lH-indole-7- carboxylate To a stirred solution of methyl 2-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-indole-7- carboxylate (370 mg), tris(dibenzylideneacetone)dipalladium(0) (30 mg), 1,2,3,4,5-pentaphenyl-T- (di-tert-butylphosphino)ferrocene (30 mg) and potassium phosphate (550 mg) in tetrahydrofuran (2 mL) was added Example 1.1.11 (735 mg). The mixture was purged with nitrogen and stirred at 70 °C for 3 hours. The reaction was diluted with ethyl acetate and washed with water and brine. The aqueous layer was back extracted by ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated. The residue was purified via silica gel chromatography, eluting with 0-20% ethyl acetate in heptanes, to give the title compound. MS (ESI) m/e 780.4 (M-H) .
	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene In tetrahydrofuran at 70℃; for 3h; Inert atmosphere;	1.27.1 1.27 .1 methyl 2-( 6-(tert-butoxycarbonyl)-5-(1-( (3-(2-( ( tertbutoxycarbonyl)(methyl)amino )ethoxy)-5, 7 -dimethyladamantan-1-yl)methyl)-5-methyl-1H -pyrazol-4-yl)pyridin-2-yl)-1H -indole-7-carboxylate To a stirred solution ofmethyl2-(4,4,5,5-tetramethyl-I,3,2-dioxaborolan-2-yl)-IH-indole-7-30 carboxylate (370 mg), tris( dibenzylideneacetone )dipalladium(O) (30 mg), I ,2,3,4,5-pentaphenyl-I'(di-tert-butylphosphino)ferrocene (30 mg) and potassium phosphate (550 mg) in tetrahydrofuran (2mL) was added Example 1.1.11 (735 mg). The mixture was purged with nitrogen and stirred at 70 ocfor 3 hours. The reaction was diluted with ethyl acetate and washed with water and brine. Theaqueous layer was back extracted by ethyl acetate. The combined organic layers were dried over35 sodium sulfate, filtered and concentrated. The residue was purified via silica gel chromatography eluting with 0-20% ethyl acetate in heptanes, to give the title compound. MS (ESI) m/e 780.4 (M-H)

Reference： [1]Current Patent Assignee: ABBVIE INC - US2016/158377, 2016, A1 Location in patent: Paragraph 0780
[2]Current Patent Assignee: ABBVIE INC - WO2017/214458, 2017, A2 Location in patent: Page/Page column 384
[3]Current Patent Assignee: ABBVIE INC - WO2017/214301, 2017, A1 Location in patent: Page/Page column 329; 330

2
[ 1942056-56-5 ]
[ 1150271-42-3 ]
[ 1942056-85-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane In tetrahydrofuran; water Reflux;	1.74.1 1.74.1 methyl 2-[5-{1-[(3-{2-[bis(tert-butoxycarbonyl)amino]ethoxy}-5,7-dimethyltricyclo[3.3.1.1^3,7]dec-1-yl)methyl]-5-methyl-1H-pyrazol-4-yl}-6-(tert-butoxycarbonyl)pyridin-2-yl]-1H-indole-7-carboxylate To a solution of Example 1.2.1 (2.25 g) in tetrahydrofuran (30 mL) and water (10 mL) was added Example 1.1.6 (2.0 g), 1,3,5,7-tetramethyl-6-phenyl-2,4,8-trioxa-6-phosphaadamantane (329 mg), tris(dibenzylideneacetone)dipalladium(0) (206 mg) and potassium phosphate tribasic (4.78 g). The mixture was refluxed overnight, cooled and diluted with ethyl acetate (500 mL). The resulting mixture was washed with water and brine, and the organic layer was dried over sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography, eluting with 20% ethyl acetate in heptanes followed by 5% methanol in dichloromethane, to provide the title compound.. Example 1.74.1 was prepared by substituting methyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-7-carboxylate for Example 1.2.1 and substituting Example 1.68.4 for Example 1.1.6 in Example 1.1.12. MS (ESI) m/e 866.3 (M-H)-.

Reference： [1]Current Patent Assignee: ABBVIE INC - US2017/355769, 2017, A1 Location in patent: Paragraph 1773

3
[ 1150271-42-3 ]
[ 2379362-37-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: XPhos; chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II); caesium carbonate / 1,4-dioxane; water / 3 h / 90 °C 2: hydroxylamine; sodium hydroxide / methanol; tetrahydrofuran; water / 2 h / 20 °C