50488-44-3|4-Bromo-2-methylquinoline| Ambeed

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Quality Control of [ 50488-44-3 ] Purity: 97% SDS Specification

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Product Details of [ 50488-44-3 ]

CAS No. :	50488-44-3
Formula :	C₁₀H₈BrN
M.W :	222.08
SMILES Code :	CC1=NC2=CC=CC=C2C(Br)=C1
MDL No. :	MFCD02278398
InChI Key :	BGIRQGWGBRSRGK-UHFFFAOYSA-N
Pubchem ID :	15560677

Safety of [ 50488-44-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 50488-44-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	10
Fraction Csp3	0.1
Num. rotatable bonds	0
Num. H-bond acceptors	1.0
Num. H-bond donors	0.0
Molar Refractivity	54.41
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	12.89 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.39
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	3.53
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.31
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	2.85
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	3.6
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.14

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-4.06
Solubility	0.0195 mg/ml ; 0.0000876 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.48
Solubility	0.0727 mg/ml ; 0.000327 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-4.95
Solubility	0.00251 mg/ml ; 0.0000113 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	Yes
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.15 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<2.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.51

Application In Synthesis of [ 50488-44-3 ]

* 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.

Upstream synthesis route of [ 50488-44-3 ]
Downstream synthetic route of [ 50488-44-3 ]

[ 50488-44-3 ] Synthesis Path-Upstream 1~6

1
[ 607-67-0 ]
[ 50488-44-3 ]

Yield	Reaction Conditions	Operation in experiment
36%	at 130℃;	(4a) 4-Hydroxy-2-methylquinoline (17.4 g, 109 mmol) and phosphorus oxytribromide (47.1 g, 164 mmol) were added to a round-bottom flask. The mixture was heated to 130° C. for several hours. After cooling to rt, the residue was partitioned between saturated Na2CO3 and ethyl acetate. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (5.x.300 mL). The combined organic layer was washed with H2O (2.x.400 mL) and brine (1.x.400 mL) and dried over MgSO4. After filtration and concentration, the residue was purified on silica gel to provide 4-bromo-2-methylquinoline (8.8 g, 36percent).
16%	With phosphorus tribromide In N,N-dimethyl-formamide at 0 - 20℃; for 3 h;	2-Methylquinolin-4-ol (4.46 g, 28.0 mmol) and N,N-dimethylformamide (80 mL) were added to a 250 mL single-neck flask, then to the mixture in flask was added dropwise phosphorus tribromide (11.37 g, 42 mmol) at 0 °C. After the addition, the reaction mixture was stirred at rt for 3 h. To the reaction mixture was added ice-water (100 mL) and ammonium hydroxide (100 mL, 25percent), then the resulting mixture was extracted with ethyl acetate (100 mL x 2). The combined organic layers were washed with saturated brine (100 mL), dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated in vacuo. The residue was purified by silica-gel column chromatography (ethyl acetate/petroleum ether (v/v) = 1/10) to give the title compound as light yellow liquid (0.995 g, 16percent).MS (ES-API, pos. ion) m/z: 222.9 [M + 2]t

References: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 7, p. 1865 - 1870.
[2] Patent: US2003/229084, 2003, A1, . Location in patent: Page/Page column 33.
[3] Patent: WO2017/36404, 2017, A1, . Location in patent: Page/Page column 130.
[4] Patent: EP96214, 1991, B1, .
[5] European Journal of Medicinal Chemistry, 2013, vol. 69, p. 527 - 536.

2
[ 1076-28-4 ]
[ 50488-44-3 ]

Yield	Reaction Conditions	Operation in experiment
19%	With N,N-dimethyl-formamide; phosphorus(V) oxybromide In dichloromethane at 0 - 25℃; for 6 h; Inert atmosphere	General procedure: To a stirred solution of the appropriate azine N-oxides in anhydrous CH₂Cl₂ (0.1 M) at 0 °C is added POBr₃ (1.2 equiv) followed by dropwise addition of DMF (0.5 equiv) under argon. The resulting reaction mixture was warmed to 25 °C and stirred for several hours until the reaction is complete as indicated by TLC. Saturated aqueous sodium carbonate solution is added to the reaction mixture slowly to adjust the pH to 7–8. The resulting mixture is separated and the aqueous phase is extracted with CH₂Cl₂ thoroughly. The organic phase is combined and washed with brine, dried over Na₂SO₄, filtered and concentrated under reduced pressure to afford the crude product, which is purified by flash column chromatography using PE/EA (100:1) as eluent.

References: [1] Tetrahedron, 2016, vol. 72, # 38, p. 5762 - 5768.

3
[ 607-66-9 ]
[ 7789-59-5 ]
[ 50488-44-3 ]

References: [1] Patent: US2003/87882, 2003, A1, .

4
[ 607-67-0 ]
[ 7789-59-5 ]
[ 50488-44-3 ]

References: [1] Patent: US2003/130273, 2003, A1, .

5
[ 62-53-3 ]
[ 50488-44-3 ]

References: [1] European Journal of Medicinal Chemistry, 2013, vol. 69, p. 527 - 536.
[2] Patent: WO2017/36404, 2017, A1, .

6
[ 607-67-0 ]
[ 50488-44-3 ]
[ 500349-69-9 ]

References: [1] Journal of Organic Chemistry, 1947, vol. 12, p. 456,457.

[ 50488-44-3 ] Synthesis Path-Downstream 1~35

1
[ 50488-44-3 ]
[ 1571-08-0 ]
[ 461665-75-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1865 - 1870.

2
[ 607-67-0 ]
[ 50488-44-3 ]

Yield	Reaction Conditions	Operation in experiment
36%	With phosphorus(V) oxybromide; at 130℃;	(4a) 4-Hydroxy-2-methylquinoline (17.4 g, 109 mmol) and phosphorus oxytribromide (47.1 g, 164 mmol) were added to a round-bottom flask. The mixture was heated to 130 C. for several hours. After cooling to rt, the residue was partitioned between saturated Na2CO3 and ethyl acetate. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (5×300 mL). The combined organic layer was washed with H2O (2×400 mL) and brine (1×400 mL) and dried over MgSO4. After filtration and concentration, the residue was purified on silica gel to provide 4-bromo-2-methylquinoline (8.8 g, 36%).
16%	With phosphorus tribromide; In N,N-dimethyl-formamide; at 0 - 20℃; for 3h;	2-Methylquinolin-4-ol (4.46 g, 28.0 mmol) and N,N-dimethylformamide (80 mL) were added to a 250 mL single-neck flask, then to the mixture in flask was added dropwise phosphorus tribromide (11.37 g, 42 mmol) at 0 C. After the addition, the reaction mixture was stirred at rt for 3 h. To the reaction mixture was added ice-water (100 mL) and ammonium hydroxide (100 mL, 25%), then the resulting mixture was extracted with ethyl acetate (100 mL x 2). The combined organic layers were washed with saturated brine (100 mL), dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated in vacuo. The residue was purified by silica-gel column chromatography (ethyl acetate/petroleum ether (v/v) = 1/10) to give the title compound as light yellow liquid (0.995 g, 16%).MS (ES-API, pos. ion) m/z: 222.9 [M + 2]t
	With phosphorus(V) oxybromide;	A. 4-Bromo-2-methylquinoline 2-Methyl-4-quinolinol (19.0g, 0.119 mole) and phosphoryl bromide (80g, 0.279 mole) were heated at 140 with stirring for 3 hours. The resulting black syrup was poured into ice water and the mixture stirred vigorously for 1 hour. The pH was adjusted to 10 with sodium hydroxide and the oily mixture extracted with methylene chloride (4 x 100 ml). The methylene chloride solution was dried (MgSO4) and evaporated to a black oil mixed with solid (26.8g). Chromatography on a silica gel column eluted with EtOAc:hexanes/1:9 gave 4-bromo-2-bromo-methylquinoline as white needles (7.17g, 20%); mp 92.5-95 dec. Anal . Calcd for C10H7Br2: C, 39.91; H, 2.34; N, 4.65; Br, 53.10. Found: C, 39.88; H, 2.34; N 4.59; Br, 53.17. Continued elution with EtOAc:hexanes/85:15 gave 4-bromo-2-methylquinoline as a pale yellow liquid (14.11g, 53%); the structure was confirmed by 1H-NMR. Anal . Calcd for C10H8Br: C, 54.08; H, N, 6.31; Br, 35.98. Found: C, 54.13; H, 3.17; N, 6.27; Br, 35.85.

With phosphorus tribromide; In N,N-dimethyl-formamide; at 0 - 20℃; for 3h;

General procedure: Phosphorous tribromide (7.3g, 27.1mmol) was added drop wise to a solution of compounds (8e) (3.6g, 22.7mmol) in DMF (40mL) at 0C. After complete addition, the reaction mass allow to room temperature and stirred for 3 hours. After completion of the reaction, transferred the reaction mass to crushed ice and neutralized with aqueous ammonia. The precipitated solid obtained was filtered, and dried. The pure compound isolated by column chromatography using silica gel 230-400, eluting with 10% ethyl acetate in hexane.

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1865 - 1870.
[2]Patent: US2003/229084,2003,A1 .Location in patent: Page/Page column 33.
[3]Patent: WO2017/36404,2017,A1 .Location in patent: Page/Page column 130.
[4]Patent: EP96214,1991,B1 .
[5]European Journal of Medicinal Chemistry,2013,vol. 69,p. 527 - 536.

3
[ 50488-44-3 ]
[ 461665-77-0 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1865 - 1870.

4
[ 50488-44-3 ]
[ 461665-78-1 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1865 - 1870.

5
[ 50488-44-3 ]
[ 461665-76-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1865 - 1870.

6
[ 50488-44-3 ]
[ 936491-30-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1865 - 1870.

7
[ 50488-44-3 ]
(3R,4R)-N-hydroxy-4-({4-[(2-methyl-4-quinolinyl)methyl]benzoyl}amino)tetrahydro-2H-pyran-3-carboxamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1865 - 1870.

8
[ 607-66-9 ]
[ 7789-59-5 ]
[ 50488-44-3 ]

Yield	Reaction Conditions	Operation in experiment
		(53a) 2-hydroxy-4-methylquinoline (17.4 g, 109 mmol) and phosphorus oxytribromide (47.1 g, 164 mmol) were added to a round-bottom flask. The mixture was heated to 130 C. for several hours. After cooling down to room temperature, the residue was partitioned between saturated Na2CO3 and ethyl acetate. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (5 x 300 mL). The combined organic layer was washed with H2O (2 x 400 mL) and brine (1 x 400 mL) and dried over MgSO4. After filtration and concentration, the residue was purified on silica gel to provide 4-bromo-2-methylquinoline (53a) (8.8 g, 36%). MS (AP+): 224 (M+1).

References: [1]Patent: US2003/87882,2003,A1 .

9
[ 607-67-0 ]
[ 7789-59-5 ]
[ 50488-44-3 ]

Yield	Reaction Conditions	Operation in experiment
		(209a) 4-hydroxy-2-methylquinoline (17.4 g, 109 mmol) and phosphorus oxytribromide (47.1 g, 164 mmol) were added to a round-bottom flask. The mixture was heated to 130 C. for several hours. After cooling down to room temperature, the residue was partitioned between saturated Na2CO3 and ethyl acetate. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (5300 mL). The combined organic layer was washed with H2O (2400 mL) and brine (1*400 mL) and dried over MgSO4. After filtration and concentration, the residue was purified on silica gel to provide 4-bromo-2-methylquinoline, 209a(8.8 g, 36%). MS (AP+): 224 (M+1).

References: [1]Patent: US2003/130273,2003,A1 .

10
[ 50488-44-3 ]
[ 461665-75-8 ]

Yield	Reaction Conditions	Operation in experiment
65%	With n-butyllithium; lithium; In tetrahydrofuran; methyl 4-formylbenzoate;	(53b) <strong>[50488-44-3]4-Bromo-2-methylquinoline</strong> (53a) (1.0 g, 4.5 mmol) was dissolved in 10 mL of anhydrous THF and the resulting solution was cooled down to -78 C. A solution of n-BuLi (3.0 mL, 1.6M, 4.8 mmol) was added slowly and the resulting solution was maintained at -78 C. for 5 min. Meanwhile, in another flask methyl 4-formylbenzoate (0.9 g, 5.4 mmol) was dissolved in 20 mL of anhydrous THF and the resulting solution was cooled to -78 C. before the lithium reagent made above was cannulated. The whole mixture was stirred for 30 min before quenched with MeOH. The solution was then diluted with ethyl acetate and washed with H2O and brine. After dried over MgSO4, the organic solution was filtered and concentrated. The residue was purified on silica gel to provide methyl 4-[hydroxy(2-methyl-4-quinolinyl)methyl]benzoate (0.9 g, 65%). MS (AP+): 308 (M+1).
65%	With n-butyllithium; lithium; In tetrahydrofuran; methyl 4-formylbenzoate;	(209b) <strong>[50488-44-3]4-Bromo-2-methylquinoline</strong>, 209a (1.0 g, 4.5 mmol) was dissolved in 10 mL of anhydrous THF and the resulting solution was cooled down to -78 C. A solution of n-BuLi (3.0 mL, 1.6M, 4.8 mmol) was added slowly and the resulting solution was maintained at -78 C. for 5 min. Meanwhile, in another flask methyl 4-formylbenzoate (0.9 g, 5.4 mmol) was dissolved in 20 mL of anhydrous THF and the resulting solution was cooled to -78 C. before the lithium reagent made above was cannulated. The whole mixture was stirred for 30 min before quenched with MeOH. The solution was then diluted with ethyl acetate and washed with H2O and brine. After dried over MgSO4, the organic solution was filtered and concentrated. The residue was purified on silica gel to provide methyl 4-[hydroxy(2-methyl-4-quinolinyl)methyl]benzoate (0.9 g, 65%). MS (AP+): 308 (M+1).
65%	With n-butyllithium; lithium; In tetrahydrofuran; methyl 4-formylbenzoate;	(401b) <strong>[50488-44-3]4-Bromo-2-methylquinoline</strong> (401a) (1.0 g, 4.5 mmol) was dissolved in 10 mL of anhydrous THF and the resulting solution was cooled down to -78 C. A solution of n-BuLi (3.0 mL, 1.6M, 4.8 mmol) was added slowly and the resulting solution was maintained at -78 C. for 5 min. Meanwhile, in another flask methyl 4-formylbenzoate (0.9 g, 5.4 mmol) was dissolved in 20 mL of anhydrous THF and the resulting solution was cooled to -78 C. before the lithium reagent made above was cannulated. The whole mixture was stirred for 30 min before quenched with MeOH. The solution was then diluted with ethyl acetate and washed with H2O and brine. After dried over MgSO4, the organic solution was filtered and concentrated. The residue was purified on silica gel to provide methyl 4-[hydroxy(2-methyl-4-quinolinyl)methyl]benzoate (0.9 g, 65%). MS (AP+): 308 (M+1).

References: [1]Patent: US2003/87882,2003,A1 .
[2]Patent: US2003/130273,2003,A1 .
[3]Patent: US2003/139388,2003,A1 .

11
[ 50488-44-3 ]
1-methylcarboxyphenylboronic acid [ No CAS ]
[ 477585-40-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate;Pd(PPh3)4; In tetrahydrofuran; aq K2CO3; ethyl acetate;	Example 220 4-(2-methyl-4-quinolinyl)benzoic Acid To 1-methylcarboxyphenylboronic acid (1.0 g, 5.6 mmol) and <strong>[50488-44-3]4-bromo-2-methylquinoline</strong> (1.24 g, 5.6 mmol) in THF/aq K2CO3 was added Pd(PPh3)4 and the reaction was heated to 70 C. for 16 hr. Aqueous workup using NaHCO3 and EtOAc, column chromatography and saponification using the same conditions as for Example 214 gave the final productproduct. MS found: (M+H) 264.

References: [1]Patent: US2003/130273,2003,A1 .

12
[ 50488-44-3 ]
of(+-)-[1,4]-diazepan-2-carboxamide [ No CAS ]
[ 108-95-2 ]
[ 220364-71-6 ]

Yield	Reaction Conditions	Operation in experiment
	In potassium iodide;	EXAMPLE 39 (+-)-1,4-Bis-(2-methyl-quinolin-4-yl)-[1,4]-diazepan-2-carboxamide STR35 Analogously to the instructions in Example 26, 0.026 g (6.1%) of the title compound is prepared (colourless crystals) from 0.143 g(1 mmol) of(+-)-[1,4]-diazepan-2-carboxamide, 0.445 g (2 mmol) of <strong>[50488-44-3]4-bromo-2-methylquinoline</strong> and 0.03 g (0.3 mmol) of phenol over 14.5 hours at 100 C. in the presence of 0.03 g of potassium iodide. M.p.: 130 to 131 C.; Yield: 0.88 g (77%)

References: [1]Patent: US5866562,1999,A .

13
[ 50488-44-3 ]
[ 6760-22-1 ]

Yield	Reaction Conditions	Operation in experiment
34%	With hydrogenchloride; n-butyllithium; In tetrahydrofuran; N-methyl-acetamide; ethanol;	B. 2-Methyl-4-quinolinecarbaldehyde To a solution of <strong>[50488-44-3]4-bromo-2-methylquinoline</strong> (4.71g, 21.2 mmol) in dry tetrahydrofuran (50 ml) under nitrogen at -78 was added 1.5M n-butyllithium in hexanes (13.5 ml). After 2 minutes, dry dimethylformamide (2.0 ml, 25 mmol) was added. After an additional 3 minutes at -78, ethanol (5 ml) was added, followed by 1N hydrochloric acid. After 5 minutes, at 25, the solution was neutralised with sodium hydroxide and extracted with methylene chloride (4 x 50ml). The methylene chloride solution was dried (MgSO4) and passed through a silica gel pad to give the title compound as yellow crystals (1.24g, 34%);, mp 72-75. Anal . Calcd for C11H9NO1/10H2O: C, 76.37; H, 5.36; N, 8.10. Found: C, 76.13; H, 5.44; N, 7.96.

References: [1]Patent: EP96214,1991,B1 .

14
[ 50488-44-3 ]
[ 6628-04-2 ]

References: [1]Chemical Communications,2009,p. 3035 - 3037.

15
[ 62-53-3 ]
[ 50488-44-3 ]

References: [1]European Journal of Medicinal Chemistry,2013,vol. 69,p. 527 - 536.
[2]Patent: WO2017/36404,2017,A1 .

16
[ 50488-44-3 ]
[ 91-63-4 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; In tetrahydrofuran; at -78℃; for 0.5h;	2.5M n-Butyl lithium (7.5mL, 18.9mmol) was added to the solution of compounds (10e) (3.5g, 15.7mmol) in dry THF(30mL) at -78C and stirred for 30 min. Reaction was quenched with aqueous NH4Cl solution (5mL) and warmed to 0C. Ice cold water was added to the reaction mixture and extracted with ethyl acetate. The organic layer was washed with water, brine solution and dried over sodium sulphate, concentrated under reduced pressure. The crude product was triturated with 20% diethyl ether in hexane to afford the title compounds.

References: [1]European Journal of Medicinal Chemistry,2013,vol. 69,p. 527 - 536.

17
[ 50488-44-3 ]
[ 5470-96-2 ]

References: [1]European Journal of Medicinal Chemistry,2013,vol. 69,p. 527 - 536.

18
[ 50488-44-3 ]
3-(quinolin-2-yl)prop-2-enoic acid [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2013,vol. 69,p. 527 - 536.

19
[ 50488-44-3 ]
[ 128674-56-6 ]

References: [1]European Journal of Medicinal Chemistry,2013,vol. 69,p. 527 - 536.

20
[ 50488-44-3 ]
2-[fluoroprop-1-en-1-yl]quinoline [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2013,vol. 69,p. 527 - 536.

21
[ 50488-44-3 ]
C₁₂H₁₀N₂O [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2013,vol. 69,p. 527 - 536.

22
[ 50488-44-3 ]
[ 53574-67-7 ]

References: [1]European Journal of Medicinal Chemistry,2013,vol. 69,p. 527 - 536.

23
[ 50488-44-3 ]
[ 13235-12-6 ]