[ CAS No. 1123169-45-8 ] {[proInfo.proName]}

Name: 1123169-45-8|tert-Butyl 6-bromo-3,4-dihydroquinoline-1(2H)-carboxylate|97%
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SKU: A424289
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Quality Control of [ 1123169-45-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1123169-45-8 ]

Product Details of [ 1123169-45-8 ]

CAS No. :	1123169-45-8	MDL No. :	MFCD11858570
Formula :	C₁₄H₁₈BrNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HXVKARGTRMNFQU-UHFFFAOYSA-N
M.W :	312.20	Pubchem ID :	53408384
Synonyms :

Calculated chemistry of [ 1123169-45-8 ]

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.5
Num. rotatable bonds :	3
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	79.88
TPSA :	29.54 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.54 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.49
Log Po/w (XLOGP3) :	3.75
Log Po/w (WLOGP) :	3.76
Log Po/w (MLOGP) :	3.44
Log Po/w (SILICOS-IT) :	3.11
Consensus Log Po/w :	3.51

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.19
Solubility :	0.0203 mg/ml ; 0.000065 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.06
Solubility :	0.027 mg/ml ; 0.0000865 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-4.3
Solubility :	0.0157 mg/ml ; 0.0000504 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.55

Safety of [ 1123169-45-8 ]

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 [ 1123169-45-8 ]

* 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 [ 1123169-45-8 ]
Downstream synthetic route of [ 1123169-45-8 ]

[ 1123169-45-8 ] Synthesis Path-Upstream 1~1

1
[ 22190-35-8 ]
[ 24424-99-5 ]
[ 1123169-45-8 ]

Yield	Reaction Conditions	Operation in experiment
40.7%	With sodium hydroxide In tetrahydrofuran; water at 20℃; for 12 h;	[00336] Step 1. To a stirred solution of bromo-tetrahydroquinoline 1-A (5 g, 23.7 mmol) in 60 mL of THF was added a solution of NaOH (lg, 25 mmol) in H₂0 (30 mL). Ditertbutyl dicarbonate (5.37 g, 25 mmol) was added. The mixture was stirred for 12 hours at room temperature. Solvent was removed in vacuo, and the aqueous mixture was extracted with EtOAc (50 mL x 3). The combined organic extracts were washed with brine, dried over anhydrous Na₂S0₄, concentrated and purified with column chromatography to provide the boc-protected compound 17-A as a colorless solid (3 g, 40.7percent). 1H NMR (300 MHz, CDC13): δ 7.56 - 7.53 (m, 1H), 7.24 - 7.19 (m, 2H), 3.70 - 3.66 (m, 2H), 2.75 - 2.71 (m, 2H), 1.92 - 1.88 (m, 2H), 1.52 (s, 9H).

Reference： [1] ChemMedChem, 2018, vol. 13, # 14, p. 1405 - 1413
[2] Patent: WO2014/8214, 2014, A1, . Location in patent: Paragraph 00335-00336

[ 1123169-45-8 ] Synthesis Path-Downstream 1~24

1
[ 1123169-45-8 ]
[ 1338782-29-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5701 - 5706

2
[ 1123169-45-8 ]
[ 1338782-36-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5701 - 5706

3
[ 1123169-45-8 ]
[ 1279870-64-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5701 - 5706

4
[ 1123169-45-8 ]
[ 15532-75-9 ]
[ 1338782-43-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5701 - 5706

5
[ 1123169-45-8 ]
[ 1532517-58-0 ]

Reference： [1]Patent: WO2014/8214,2014,A1

6
[ 1123169-45-8 ]
[ 1150114-35-4 ]
[ 1532517-57-9 ]

Yield	Reaction Conditions	Operation in experiment
56%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In N,N-dimethyl-formamide; at 100℃;	[00337] Step 2. 5-Carbamoyl-2-chlorophenylboronic acid 8-D (0.7g, 3.5 mmol) was added to a stirred mixture of 17-A (l.Og, 3.2 mmol), Pd(dppf)Cl2 (0.26 g, 0.32 mmol) and K2C03 (0.88 g, 6.4 mmol) in DMF (40 mL). The mixture was heated at 100C overnight. Solvent was removed under reduced pressure, and the residue was purified by column chromatography eluting with PE/EA (1: 1) to afford the intermediate 17-B as a colorless solid (0.76 g, 56%). 1H NMR (300 MHz, CD3OD): delta 7.87 - 7.21 (m, 6H), 3.91 - 3.51 (m, 2H), 2.84 (dd, J = 10.8, 4.3 Hz, 2H), 2.00 - 1.81 (m, 2H), 1.55 (s, 9H).

Reference： [1]Patent: WO2014/8214,2014,A1 .Location in patent: Paragraph 00335; 00337

7
[ 22190-35-8 ]
[ 24424-99-5 ]
[ 1123169-45-8 ]

Yield	Reaction Conditions	Operation in experiment
40.7%	With sodium hydroxide; In tetrahydrofuran; water; at 20℃; for 12h;	[00336] Step 1. To a stirred solution of bromo-tetrahydroquinoline 1-A (5 g, 23.7 mmol) in 60 mL of THF was added a solution of NaOH (lg, 25 mmol) in H20 (30 mL). Ditertbutyl dicarbonate (5.37 g, 25 mmol) was added. The mixture was stirred for 12 hours at room temperature. Solvent was removed in vacuo, and the aqueous mixture was extracted with EtOAc (50 mL x 3). The combined organic extracts were washed with brine, dried over anhydrous Na2S04, concentrated and purified with column chromatography to provide the boc-protected compound 17-A as a colorless solid (3 g, 40.7%). 1H NMR (300 MHz, CDC13): delta 7.56 - 7.53 (m, 1H), 7.24 - 7.19 (m, 2H), 3.70 - 3.66 (m, 2H), 2.75 - 2.71 (m, 2H), 1.92 - 1.88 (m, 2H), 1.52 (s, 9H).
	In toluene; at 110℃;	To a solution of <strong>[22190-35-8]6-bromo-1,2,3,4-tetrahydroquinoline</strong> (175A) (1.3 g, 6.1 mmol) in toluene (20 mL) was added Boc2O (1.6 g, 7.4 mmol). The reaction mixture was stirred at 110 C overnight and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate in petroleum ether, 20% v/v) to furnish Compound 175B. LC-MS (ESI) m/z: 255 [M-56]t

Reference： [1]ChemMedChem,2018,vol. 13,p. 1405 - 1413
[2]Patent: WO2014/8214,2014,A1 .Location in patent: Paragraph 00335-00336
[3]Patent: WO2019/133770,2019,A2 .Location in patent: Paragraph 001141; 001142; 001143

8
[ 1123169-45-8 ]
C₂₇H₃₅N₃O₅S [ No CAS ]

Reference： [1]ChemMedChem,2018,vol. 13,p. 1405 - 1413

9
[ 1123169-45-8 ]
C₂₂H₂₇N₃O₃S [ No CAS ]

Reference： [1]ChemMedChem,2018,vol. 13,p. 1405 - 1413

10
[ 1123169-45-8 ]
tert-butyl 6-(chlorosulfonyl)-3,4-dihydroquinoline-1(2H)-carboxylate [ No CAS ]

Reference： [1]ChemMedChem,2018,vol. 13,p. 1405 - 1413

11
[ 1123169-45-8 ]
[ 100-53-8 ]
tert-butyl 6-(benzylthio)-3,4-dihydroquinoline-2(1H)-carboxylate [ No CAS ]

Reference： [1]ChemMedChem,2018,vol. 13,p. 1405 - 1413

12
[ 1123169-45-8 ]
tert-butyl (R,E)-6-(3-(2-(tert-butoxycarbonyl)-3-oxo-2,3-dihydrobenzofuran-2-yl)prop-1-en-1-yl)-3,4-dihydroquinoline-1(2H)-carboxylate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2018,vol. 140,p. 10658 - 10662

13
[ 1123169-45-8 ]
[ 24850-33-7 ]
tert-butyl 6-allyl-3,4-dihydroquinoline-1(2H)-carboxylate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2018,vol. 140,p. 10658 - 10662

14
[ 1123169-45-8 ]
[ 68-12-2 ]
tert-butyl 6-formyl-3,4-dihydroquinoline-1(2H)-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a stirred solution of tert-butyl 6-bromo-3.4-dihydroquinoline-l(2H)- carboxylate (600 mg, 1.92 mmol) in THF (20 mL) at -78 C under nitrogen atmosphere, n- butyllithium (0.85 mL, 2.13 mmol) was added dropwise. After stirring for 1 h at -78 C, DMF (0.24 mL, 3.10 mmol) was added at -78 C and the reaction was monitored by LCMS and TLC (Pet. ether: EtOAc = 5: 1). It was found that the reaction was finished after stirring for 4 h at - 78 C and 2 h at 20 C. The mixture was quenched with aq. NH4C1 (10 mL), and diluted with EtOAc (40 mL). The organic layer was separated, and the aqueous layer was extracted with EtOAc (30 mLx2), the combined organic layers were washed with brine (30 mL), dried over Na2S04, filtered and concentrated. The residue was purified by column chromatography (SiC>2. EtOAc in Pet. ether: 0 to 7%) to give the title compound as an oil. ESI MS m/z 262.1 [M+H+].

Reference： [1]Patent: WO2019/89412,2019,A1 .Location in patent: Page/Page column 110

15
[ 1123169-45-8 ]
2-(1-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroquinolin-6-yl)-2-methoxyacetic acid [ No CAS ]