[ CAS No. 159503-91-0 ] {[proInfo.proName]}

Name: 159503-91-0|tert-Butyl 4-bromo-5,6-dihydropyridine-1(2H)-carboxylate|95%
Brand: Ambeed
SKU: A135591
Price: 6.0 USD
Availability: InStock
Rating: 91 (35 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

DV 2D 3D

3d Animation Molecule Structure of 159503-91-0

Structure of 159503-91-0 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 159503-91-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 159503-91-0 ]

SDS Specification

Alternatived Products of [ 159503-91-0 ]

Product Details of [ 159503-91-0 ]

CAS No. :	159503-91-0	MDL No. :	MFCD13181893
Formula :	C₁₀H₁₆BrNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PQILACDFDBWRNK-UHFFFAOYSA-N
M.W :	262.14	Pubchem ID :	44239841
Synonyms :

Calculated chemistry of [ 159503-91-0 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.7
Num. rotatable bonds :	3
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	63.99
TPSA :	29.54 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) :	-6.33 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.01
Log Po/w (XLOGP3) :	2.21
Log Po/w (WLOGP) :	2.53
Log Po/w (MLOGP) :	2.04
Log Po/w (SILICOS-IT) :	1.7
Consensus Log Po/w :	2.3

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.66
Solubility :	0.574 mg/ml ; 0.00219 mol/l
Class :	Soluble
Log S (Ali) :	-2.46
Solubility :	0.899 mg/ml ; 0.00343 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.11
Solubility :	2.03 mg/ml ; 0.00776 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	3.42

Safety of [ 159503-91-0 ]

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 [ 159503-91-0 ]

* 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 [ 159503-91-0 ]
Downstream synthetic route of [ 159503-91-0 ]

[ 159503-91-0 ] Synthesis Path-Upstream 1~3

1
[ 79099-07-3 ]
[ 159503-91-0 ]

Yield	Reaction Conditions	Operation in experiment
80%	With triphenyl phosphite; bromine; triethylamine In dichloromethane at -25 - -20℃;	1st step: in the reaction bottle, will N-Boc-4-piperidone (19.9g, 0 . 1mol), triphenyl phosphite (34.1g, 0 . 11mol) and triethylamine (15.2g, 0 . 15mol) dissolved in 160 ml of methylene chloride, temperature control -25 ° C to -20 °C, instillment bromide (17.6g, 0 . 11mol) in dichloromethane (30 ml) solution, completion of the dropping, the stirring reaction heat. TLC detection after the reaction, the solvent is distilled under reduced pressure, subsequently joined 300mL95percent cold ethanol after stirring, the solid is filtered, the filtrate to dryness, by adding 150 ml of toluene and 40 ml moisture content level, toluene layer saturated salt water washing, solvent to obtain organic solvent turns on lathe does N-Boc-1, 2, 5, 6-tetrahydro-pyridine-4-bromo, internal standard calibration the yield is 80percent;
72%	With triphenyl phosphite; triethylamine In dichloromethane at -25 - -15℃;	1st step: in the reaction bottle, will N-Boc-4-piperidone (19.9g, 0 . 1mol), triphenyl phosphite (34.1g, 0 . 11mol) and triethylamine (15.2g, 0 . 15mol) dissolved in 160 ml of methylene chloride, temperature control -25 ° C to -15 °C, slow instillment bromide (19.2g, 0 . 12mol) in dichloromethane (30 ml) solution, completion of the dropping, the stirring reaction heat. TLC detection after the reaction, the solvent is distilled under reduced pressure, subsequently joined 330mL95percent cold ethanol after stirring, the solid is filtered, the filtrate to dryness, by adding 45 ml after sulfolane, vacuum distillation to obtain 18.9g colorless liquid N-Boc-1, 2, 5, 6-tetrahydro-pyridine-4-bromo, yield 72percent;

Reference： [1] Patent: CN105566367, 2016, A, . Location in patent: Paragraph 0019
[2] Patent: CN105566368, 2016, A, . Location in patent: Paragraph 0019

2
[ 138647-49-1 ]
[ 159503-91-0 ]

Reference： [1] Chemical Communications, 2009, # 34, p. 5088 - 5090

3
[ 589-87-7 ]
[ 375853-82-0 ]
[ 159503-91-0 ]

Reference： [1] Patent: CN105272936, 2016, A, . Location in patent: Paragraph 0201; 0202; 0203; 0204; 0205

[ 159503-91-0 ] Synthesis Path-Downstream 1~21

1
[ 138647-49-1 ]
[ 159503-91-0 ]

Reference： [1]Chemical Communications,2009,p. 5088 - 5090

2
[ 159503-91-0 ]
(2-chloro-6-methoxypyridin-3-yl)boronic acid [ No CAS ]
tert-butyl 2-chloro-6-methoxy-5',6'-dihydro-[3,4'-bipyridine]-1'(2'H)-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In N,N-dimethyl-formamide; at 100℃; for 1.0h;	Intermediate 2-23-A. tert-butyl 2-chloro-6-methoxy-5,6-dihydro-[3,4-bipyridine]- 1(2'H)-carboxylateTo a solution of (2-chloro-6-methoxypyridin-3-yl)boronic acid (CAS 1072946-25- 8 )(0.077g, 0.41 mmol) and te/ -butyl 4-bromo-5,6-dihydropyridine-1 (2H)-carboxylate (CAS 159503-91 -0)(0.14 g, 0.52 mmol) in DMF (2.1 mL) were added Pd(PPh3)4 (0.024 g, 0.021 mmol) and cesium carbonate (0.12 g, 0.37 mmol). The mixture was then stirred at 100 C for 1 h, and then cooled to room temperature. The reaction mixture was diluted with EtOAc. The organic layer was then washed with H20, dried over Na2S04, filtered, and then concentrated. The resulting residue was purified by silica gel flash column chromatography (0-50% EtOAc in heptane) to afford the title compound. MS (ESI+) m/z 269.15, 271 .1 (M-f-butyl+2H).

Reference： [1]Patent: WO2016/1876,2016,A1 .Location in patent: Page/Page column 60

3
[ 159503-91-0 ]
(2-chloro-6-methoxypyridin-3-yl)boronic acid [ No CAS ]
tert-butyl 2-ethyl-6-methoxy-5',6'-dihydro-[3,4'-bipyridine]-1'(2'H)-carboxylate [ No CAS ]

Reference： [1]Patent: WO2016/1876,2016,A1

4
[ 159503-91-0 ]
[ 1003043-40-0 ]
tert-butyl 6-chloro-5-methyl-5',6'-dihydro-[3,4'-bipyridine]-1'(2'H)-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In methanol; water; toluene; at 90.0℃; for 0.75h;	To a suspension of (6-chloro-5-methylpyridin-3-yl)boronic acid (CAS 1003043-40-0, 0.51 g, 2.98 mmol), te/ -butyl 4-bromo-5,6-dihydropyridine-1 (2H)-carboxylate (CAS 159503- 91 -0, 0.975 g, 3.72 mmol) in toluene (7.4 ml) and MeOH (7.4 ml) was added potassium carbonate (2M in water; 3.7 ml, 7.4 mmol), followed by Pd(dppf)CI2'CH2CI2 adduct (0.24 g, 0.3 mmol). The mixture was stirred at 90 C for 0.75 h, and then cooled to room temperature. The reaction mixture was diluted with EtOAc. The mixture was then washed with H20, and then passed through an ISOLUTE Phase Separator and concentrated. The residue was purified by silica gel flash column chromatography (0-50% EtOAc in heptane) to afford the title compound. MS (ESI+) m/z 309.2 (M+H).

Reference： [1]Patent: WO2016/1875,2016,A1 .Location in patent: Page/Page column 203

5
[ 589-87-7 ]
[ 375853-82-0 ]
[ 159503-91-0 ]

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; for 12.0h;Inert atmosphere; Reflux;	Compound 21 (leq) was added compound 22 (leq), followed by potassium carbonate (3eq), [1,1 '_ bis (diphenylphosphino) ferrocene] dichloropalladium (O.leq), was added 1 , 4-dioxane: water = 4: 1, vacuum pumping, replace the nitrogen, under the protection of nitrogen reflux 12h, TLC the reaction was complete after filtration, the filter cake was washed with chloroform, the filtrate was collected, concentrated, and column chromatographed to give intermediate 23.

Reference： [1]Patent: CN105272936,2016,A .Location in patent: Paragraph 0201; 0202; 0203; 0204; 0205

6
[ 79099-07-3 ]
[ 159503-91-0 ]

Yield	Reaction Conditions	Operation in experiment
80%	With triphenyl phosphite; bromine; triethylamine; In dichloromethane; at -25 - -20℃;	1st step: in the reaction bottle, will N-Boc-4-piperidone (19.9g, 0 . 1mol), triphenyl phosphite (34.1g, 0 . 11mol) and triethylamine (15.2g, 0 . 15mol) dissolved in 160 ml of methylene chloride, temperature control -25 C to -20 C, instillment bromide (17.6g, 0 . 11mol) in dichloromethane (30 ml) solution, completion of the dropping, the stirring reaction heat. TLC detection after the reaction, the solvent is distilled under reduced pressure, subsequently joined 300mL95% cold ethanol after stirring, the solid is filtered, the filtrate to dryness, by adding 150 ml of toluene and 40 ml moisture content level, toluene layer saturated salt water washing, solvent to obtain organic solvent turns on lathe does N-Boc-1, 2, 5, 6-tetrahydro-pyridine-4-bromo, internal standard calibration the yield is 80%;
72%	With triphenyl phosphite; triethylamine; In dichloromethane; at -25 - -15℃;	1st step: in the reaction bottle, will N-Boc-4-piperidone (19.9g, 0 . 1mol), triphenyl phosphite (34.1g, 0 . 11mol) and triethylamine (15.2g, 0 . 15mol) dissolved in 160 ml of methylene chloride, temperature control -25 C to -15 C, slow instillment bromide (19.2g, 0 . 12mol) in dichloromethane (30 ml) solution, completion of the dropping, the stirring reaction heat. TLC detection after the reaction, the solvent is distilled under reduced pressure, subsequently joined 330mL95% cold ethanol after stirring, the solid is filtered, the filtrate to dryness, by adding 45 ml after sulfolane, vacuum distillation to obtain 18.9g colorless liquid N-Boc-1, 2, 5, 6-tetrahydro-pyridine-4-bromo, yield 72%;

Reference： [1]Patent: CN105566367,2016,A .Location in patent: Paragraph 0019
[2]Patent: CN105566368,2016,A .Location in patent: Paragraph 0019

7
[ 79988-34-4 ]
[ 159503-91-0 ]
[ 126-30-7 ]
tert-butyl 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%		2nd step: the metal lithium (1.0g, 0 . 15mol) and double (diisopropylamine) boron bromide (21.8g, 75mmol) by adding 2-methyl tetrahydrofuran (90 ml) in, temperature control -20 C to -10 C, dripping is dissolved in 2-methyl tetrahydrofuran (35 ml) of in N-Boc-1, 2, 5, 6-tetrahydro-pyridine-4-bromo (18.9g, 72mmol), stirring after 5 hours, the end of the detection reaction, adding npg (8.6g, 83mmol), heating to reflux reaction. Cooling, adding 10% hydrochloric acid aqueous solution to adjust PH= 5-6, organic layer by adding 10% palladium carbon (1.2g), after the replacement of nitrogen, filled with 1 atmospheric pressure hydrogen, after the reaction, drying of the organic layer, by adding 45 ml normal heptane cooling -10 C pulping, filtering to obtain 14.3g kind of white solid N-Boc-piperidin-4-boronic acid new pentamethylene glycol ester, GC: 98.5%, HNMR: > 98%, yield: 67%.

Reference： [1]Patent: CN105566368,2016,A .Location in patent: Paragraph 0019

8
[ 61676-62-8 ]
[ 159503-91-0 ]
[ 375853-82-0 ]

Yield	Reaction Conditions	Operation in experiment
61%		2nd step: under the protection of nitrogen, the 1M isopropyl magnesium chloride-lithium chloride (88 ml, 88mmol) into the reaction bottle, temperature control -15 C to -5 C, dropwise N-Boc-1, 2, 5, 6-tetrahydro-pyridine-4-bromo, 2-methyl tetrahydrofuran (90 ml) solution, stirring finishing joining 1-2 hours. After the end of the exchange, then drop by adding isopropoxy boric acid pinacone ester (16.4g, 88mmol), subsequently maintain the reaction at room temperature overnight. Adding 10% hydrochloric acid aqueous solution quenching reaction, adjusting PH= 4-5, by adding 160 ml ethyl acetate, saturated salt water an organic layer, the organic layer after evaporation to dryness, add ethanol/heptane 5:1 obtained after pulping 18.9g N-Boc-1 needle-like white crystals, 2, 5, 6-tetrahydro-pyridine-4-boronic acid frequency that alcohol ester, GC: 99.6%, yield: 61%.

Reference： [1]Patent: CN105566367,2016,A .Location in patent: Paragraph 0019

9
[ 159503-91-0 ]
(1-(methoxycarbonyl)cyclopropyl)zinc(II) bromide [ No CAS ]
tert-butyl 4-(1-(methoxycarbonyl)cyclopropyl)-5,6-dihydropyridine-1(2H)-carboxylate [ No CAS ]

Reference： [1]Organic Letters,2017,vol. 19,p. 2490 - 2493

10
[ 159503-91-0 ]
tert-butyl 4-[4-(ethoxycarbonyl)phenyl]piperidine-1-carboxylate [ No CAS ]