[ CAS No. 25542-62-5 ] {[proInfo.proName]}

Name: 25542-62-5|Ethyl 6-bromohexanoate|98%
Brand: Ambeed
SKU: A122718
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Quality Control of [ 25542-62-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 25542-62-5 ]

Product Details of [ 25542-62-5 ]

CAS No. :	25542-62-5	MDL No. :	MFCD00000270
Formula :	C₈H₁₅BrO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DXBULVYHTICWKT-UHFFFAOYSA-N
M.W :	223.11	Pubchem ID :	117544
Synonyms :

Calculated chemistry of [ 25542-62-5 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.88
Num. rotatable bonds :	7
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	49.72
TPSA :	26.3 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) :	-5.86 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.8
Log Po/w (XLOGP3) :	2.53
Log Po/w (WLOGP) :	2.5
Log Po/w (MLOGP) :	2.43
Log Po/w (SILICOS-IT) :	2.55
Consensus Log Po/w :	2.56

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.36
Solubility :	0.985 mg/ml ; 0.00441 mol/l
Class :	Soluble
Log S (Ali) :	-2.73
Solubility :	0.417 mg/ml ; 0.00187 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.25
Solubility :	0.127 mg/ml ; 0.000569 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.34

Safety of [ 25542-62-5 ]

Signal Word:	Danger	Class:	3
Precautionary Statements:	P501-P240-P210-P233-P243-P241-P242-P264-P280-P370+P378-P337+P313-P305+P351+P338-P362+P364-P303+P361+P353-P332+P313-P403+P235	UN#:	3272
Hazard Statements:	H225-H315-H319	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 25542-62-5 ]

* 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 [ 25542-62-5 ]
Downstream synthetic route of [ 25542-62-5 ]

[ 25542-62-5 ] Synthesis Path-Upstream 1~12

1
[ 67-56-1 ]
[ 25542-62-5 ]
[ 14273-90-6 ]

Reference： [1] Journal of Catalysis, 2009, vol. 262, # 1, p. 18 - 26

2
[ 5299-60-5 ]
[ 25542-62-5 ]

Reference： [1] Tetrahedron Letters, 2003, vol. 44, # 44, p. 8143 - 8147
[2] Chemistry - A European Journal, 2011, vol. 17, # 40, p. 11290 - 11295
[3] Journal of the Chemical Society, 1937, p. 718,720
[4] Journal of the Indian Chemical Society, 1942, vol. 19, p. 305
[5] Journal of the Chemical Society, 1937, p. 718,720
[6] Journal of the Chemical Society, 1937, p. 718,720

3
[ 64-17-5 ]
[ 4224-70-8 ]
[ 25542-62-5 ]

Reference： [1] Journal of Organic Chemistry, 1992, vol. 57, # 21, p. 5708 - 5712
[2] New Journal of Chemistry, 2017, vol. 41, # 7, p. 2769 - 2779
[3] Organic Preparations and Procedures International, 1991, vol. 23, # 2, p. 214 - 216
[4] Journal of Organic Chemistry, 1995, vol. 60, # 21, p. 7072 - 7074
[5] Tetrahedron Letters, 2001, vol. 42, # 24, p. 3959 - 3961
[6] Journal of the Chemical Society, 1949, p. 1475
[7] Journal of the American Chemical Society, 1944, vol. 66, p. 839
[8] Annales de Chimie (Cachan, France), 1957, vol. <13>2, p. 682,700
[9] Journal fuer Praktische Chemie (Leipzig), 1970, vol. 312, p. 1058 - 1062
[10] Journal of Organic Chemistry, 1975, vol. 40, # 23, p. 3456 - 3458
[11] Journal of Medicinal Chemistry, 2012, vol. 55, # 16, p. 7163 - 7172
[12] Chinese Journal of Chemistry, 2014, vol. 32, # 2, p. 157 - 162
[13] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 5, p. 468 - 473
[14] ACS Chemical Neuroscience, 2017, vol. 8, # 9, p. 1949 - 1959
[15] Tetrahedron, 2017, vol. 73, # 44, p. 6275 - 6285

4
[ 4224-70-8 ]
[ 25542-62-5 ]

Reference： [1] Patent: EP748310, 1999, B1,
[2] Patent: US5827881, 1998, A,

5
[ 502-44-3 ]
[ 25542-62-5 ]

Reference： [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1985, vol. 24, p. 1081 - 1083
[2] Canadian Journal of Chemistry, 1983, vol. 61, p. 2016 - 2021

6
[ 1191-25-9 ]
[ 25542-62-5 ]

Reference： [1] Journal of the Chemical Society, 1949, p. 1475
[2] Journal of the American Chemical Society, 1944, vol. 66, p. 839

7
[ 29512-97-8 ]
[ 25542-62-5 ]

Reference： [1] Journal of Chemical Research, Miniprint, 1993, # 7, p. 1562 - 1572

8
[ 105-60-2 ]
[ 64-17-5 ]
[ 25542-62-5 ]

Reference： [1] Chemische Berichte, 1954, vol. 87, p. 356,362

9
[ 110-86-1 ]
[ 5299-60-5 ]
[ 7789-60-8 ]
[ 25542-62-5 ]

Reference： [1] Journal of the Chemical Society, 1937, p. 718,720

10
[ 5299-60-5 ]
[ 7664-93-9 ]
[ 10035-10-6 ]
[ 25542-62-5 ]

Reference： [1] Journal of the Chemical Society, 1937, p. 718,720

11
[ 25542-62-5 ]
[ 628-91-1 ]
[ 123-29-5 ]

Reference： [1] Angewandte Chemie - International Edition, 2004, vol. 43, # 45, p. 6180 - 6182

12
[ 25542-62-5 ]
[ 26496-94-6 ]

Reference： [1] Patent: US4804658, 1989, A,

[ 25542-62-5 ] Synthesis Path-Downstream 1~88

1
[ 64-17-5 ]
[ 4224-70-8 ]
[ 25542-62-5 ]

Yield	Reaction Conditions	Operation in experiment
91%	With hydrogenchloride; at 40℃;	To a solution of 97% 6-bromohexanoic acid (0.43 g, 2.2 mmol) in 20 mL absolute ethanol was added 0.1 mL of 37% HCl solution. The reaction mixture was stirred at 40C and monitored by TLC. After the reaction finished, it was concentrated, then diluted with Et2O and extracted with water (2 × 20 mL), dried over anhydrous sodium sulfate, and evaporated to give 0.44 g (91%) of 1l as a yellow liquid. 1H NMR (400 MHz, CDCl3) matches that reference reported.
89.2%	With thionyl chloride; for 8h;Reflux;	was added 1.56g (7.96mmol) 6- bromo-hexanoic acid (i.e., Compound 2) and 16mL of ethanol, constant pressure dropping funnel at rt 3.79g (31.84mmol) SOCl round bottom flask2after Warm to reflux for 8h.Spin off the solvent, add a small amount of water, extract twice with dichloromethane, combine the organic phases, dry over anhydrous NaSO4, filter, and spin off the solvent to obtain 1.59 g of product, which is compound 3, with a yield of 89.2%.
	With sulfuric acid; for 3h;Reflux;	General procedure: Preparation of ylides 35-37 was carried out in four steps following the reported procedure.82 The appropriate omega-bromocarboxylic acid (0.1mol) was converted to the ethyl ester by boiling in ethanol (100cm3) in the presence of H2SO4 (0.1cm3) for 3h.

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 5708 - 5712
[2]Tetrahedron Letters,2020,vol. 61
[3]New Journal of Chemistry,2017,vol. 41,p. 2769 - 2779
[4]Organic Preparations and Procedures International,1991,vol. 23,p. 214 - 216
[5]Patent: CN110698515,2020,A .Location in patent: Paragraph 0098; 0101; 0103
[6]Journal of Organic Chemistry,1995,vol. 60,p. 7072 - 7074
[7]Tetrahedron Letters,2001,vol. 42,p. 3959 - 3961
[8]Journal of the Chemical Society,1949,p. 1475
[9]Annales de Chimie (Cachan, France),1957,vol. <13>2,p. 682,700
[10]Journal fur praktische Chemie (Leipzig 1954),1970,vol. 312,p. 1058 - 1062
[11]Journal of Organic Chemistry,1975,vol. 40,p. 3456 - 3458
[12]Journal of Medicinal Chemistry,2012,vol. 55,p. 7163 - 7172
[13]Chinese Journal of Chemistry,2014,vol. 32,p. 157 - 162
[14]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 468 - 473
[15]ACS Chemical Neuroscience,2017,vol. 8,p. 1949 - 1959
[16]Tetrahedron,2017,vol. 73,p. 6275 - 6285

2
[ 25542-62-5 ]
[ 13159-24-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium iodide; In acetone; for 1h;Heating / reflux;	Ethyl 6-bromohexanoate (5.0 g, 22.4 mmol) was dissolved in anhydrous acetone (35 mL) under Ar and NaI (6.7 g, 44.8 mmol) was added. The reaction mixture was warmed at reflux for 1 h after which the acetone was removed in vacuo. The residue was taken up in EtOAc, washed with H2O, dried over Na2SO4 and concentrated to afford a quantitative yield of ethyl 6- iodohexanoate.
	With potassium iodide; In acetone; for 20h;Heating / reflux;	<Synthetic Example 1>; As a starting material for synthesizing the compound of the formula (4) of the invention, the compound 5 was prepared via the compound 2 and the compound 3 using the compound 1 as a starting material. In this connection, the compound 1 corresponds to the compound of the formula (8), the compound 2 to the compound of the formula (10), the compound 3 to the compound of the formula (5), the compound 4 to the compound of the formula (6), and the compound 5 to the compound of the formula (7). [Show Image] [Show Image] [Show Image] [Show Image] [Show Image] First, conversion of <strong>[25542-62-5]ethyl 6-bromohexanoate</strong> into ethyl 6-iodohexanoate was carried out. Namely, 39.1 g (175 mmol) of <strong>[25542-62-5]ethyl 6-bromohexanoate</strong> was dissolved in 250 ml of acetone, and 29.1 g (175 mmol) of potassium iodide was added thereto, followed by heating under reflux over a period of 20 hours. Then, after the reaction solution was allowed to cool to room temperature, the solvent was removed by distillation and the residue was extracted with 150 ml of ethyl acetate. The resulting organic layer was washed with 50 ml of distilled water and then dried over anhydrous magnesium sulfate. After drying, 47.4 g of a crude product was obtained by removing the solvent by distillation and drying under reduced pressure. As a result of 1H-NMR analysis thereof, it was found that the crude product contained ethyl 6-iodohexanoate in a molar fraction of about 90%. The crude product was used in the following step without further purification. Next, 30.5 g (155 mmol) of the compound 1 was dissolved in 450 ml of tetrahydrofuran, and the resulting solution was cooled to -78C with dry ice/acetone. To the resulting solution was dropwise added 100 ml (156 mmol) of 1.56 M n-butyllithium/n-hexane solution. After the resulting mixture was stirred at the same temperature for 45 minutes, a solution of the crude product of ethyl 6-iodohexanoate prepared in the above, which had been dissolved in 50 ml of tetrahydrofuran, was dropwise added to the mixture. After dropwise addition, the resulting mixture was stirred at the same temperature for 10 minutes and then, the temperature was gradually elevated. When the temperature of the reaction solution reached -10C, 50 ml of 5% citric acid aqueous solution was added to terminate the reaction. To the reaction mixture were added 100 ml of 10% sodium thiosulfate aqueous solution, 150 ml of saturated sodium chloride aqueous solution, and 50 ml of ethyl acetate, followed by partitioning. The organic layer was separated and the aqueous layer was extracted in 50 ml of ethyl acetate. The combined organic layer was dried over anhydrous magnesium sulfate. After drying, the solvent was removed by distillation and purification by silica gel column chromatography was carried out to obtain 49.5 g (yield 94%) of a pale yellow, liquid compound having a low viscosity. The chemical shift values of the product on 1H-NMR spectrum as measured in deuterochloroform were as follows: 1.20-1.70 (9H, m), 2.03-2.15 (2H, m), 2.23-2.35 (2H, m), 2.44 (3H, s), 3.43-3.55 (1H, m), 4.11 (2H, q), 5.04 (1H, d), 5.25-5.35 (1H, m), 5.53-5.68 (1H, m), 7.32 (2H, d), 7.70 (2H, d). The wave numbers (cm-1) with absorption on IR absorption spectrum (KBr pellet method) were as follows: 2930, 2860, 1730, 1600, 1300, 1290, 1180, 1140, 940, 670. The results of elemental analysis were as follows: carbon 64.09% and hydrogen 7.87%. Based on the above analysis, it was confirmed that the obtained compound was the compound 2. Next, conversion from the compound 2 to the compound 3 was carried out. Into 360 ml of tetrahydrofuran and 120 ml of methanol was dissolved 49.5 g (146 mmol) of the compound 2, and 3.38 g (2.92 mmol) of tetrakistriphenylphosphine palladium was added. The reaction solution was heated under reflux over a period of 16 hours. Then, after the reaction solution was allowed to cool to room temperature, the solvent was removed by distillation and purification by silica gel chromatography was carried out to obtain 47.1 g (95%) of a pale brown, liquid compound having a low viscosity. As a result of 1H-NMR analysis, IR absorption spectrum analysis, and elemental analysis shown below, it was confirmed that the product contained the compound 3 in a molar fraction of 73% and the remaining 27% was a geometrical isomer wherein the carbon-carbon double bond in the compound 3 was arranged in a cis-form. The chemical shift values of the compound 3 on 1H-NMR spectrum as measured in deuterochloroform were as follows: 1.20-1.33 (7H, m), 1.50-1.60 (2H, m), 1.99 (2H, t), 2.20-2.30 (2H, m), 2.45 (3H, s), 3.73 (2H, d), 4.08-4.15 (2H, q), 5.35-5.55 (2H, m), 7.34 (2H, d), 7.72 (2H, d). The wave numbers (cm-1) with absorption on IR absorption spectrum (KBr pellet method) were as follows: 2930, 2860, 1730, 1600, 1320, 1150, 1090, 1030, 820, 740. The results of elemental analysis were as follows: carbon 64.03% and hydrogen 7.57%. Next, conversion from the compound 3 to the compound 5 was...
	With sodium iodide; In acetone; at 20℃; for 12h;	General procedure: Preparation of ylides 35-37 was carried out in four steps following the reported procedure.82 The appropriate omega-bromocarboxylic acid (0.1mol) was converted to the ethyl ester by boiling in ethanol (100cm3) in the presence of H2SO4 (0.1cm3) for 3h. The solution was evaporated and the residue dissolved directly in A.R. acetone (50cm3). To this was added a solution of sodium iodide (18.0g, 0.12mol) in A.R. acetone (50cm3). After stirring at RT for 12h the mixture was evaporated and the residue partitioned between toluene (100cm3) and water. The toluene layer containing the iodoester was dried

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 3359 - 3368
[2]Patent: WO2008/150492,2008,A1 .Location in patent: Page/Page column 102
[3]Bioscience, Biotechnology and Biochemistry,1997,vol. 61,p. 1724 - 1728
[4]Journal of the American Chemical Society,1950,vol. 72,p. 5404,5406
[5]Tetrahedron,1999,vol. 55,p. 5741 - 5758
[6]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 6142 - 6146
[7]Patent: EP1612201,2006,A1 .Location in patent: Page/Page column 23-25
[8]Organic Letters,2016,vol. 18,p. 6038 - 6041
[9]Tetrahedron,2017,vol. 73,p. 6275 - 6285

3
[ 5299-60-5 ]
[ 25542-62-5 ]

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 8143 - 8147
[2]Chemistry - A European Journal,2011,vol. 17,p. 11290 - 11295
[3]Journal of the Chemical Society,1937,p. 718,720
[4]Journal of the Indian Chemical Society,1942,vol. 19,p. 305
[5]Journal of the Chemical Society,1937,p. 718,720
[6]Journal of the Chemical Society,1937,p. 718,720

4
[ 25542-62-5 ]
[ 15862-72-3 ]
[ 857382-91-3 ]

Reference： [1]Journal of the American Chemical Society,1952,vol. 74,p. 6251

5
[ 288-32-4 ]
[ 25542-62-5 ]
[ 72338-51-3 ]

Yield	Reaction Conditions	Operation in experiment
57%		Imidazole (1.4 g, 20.0 mmol) was added to a flask containing 15 mL of toluene.Sodium hydride (0.5 g, 20.0 mmol) was slowly added with stirring.Reflow at 120 C for 3 h, cool to room temperature,A toluene solution of ethyl bromohexanoate (2.3 g, 10.0 mmol) was slowly added dropwise, and refluxed overnight.TLC was used to detect the progress of the reaction.After the reaction was completed, it was cooled to room temperature, and toluene was concentrated and dried using a rotary evaporator.Add an appropriate amount of ethyl acetate to dissolve, and wash the organic layer with saturated sodium carbonate and brine.Drying and drying with anhydrous sodium sulfate gave a crude product.After column chromatography (DCM / MeOH = 100: 1), 1.2 g of a colorless transparent liquid (Yield = 57%),
		Take imidazole 6.8g (0.1mol), sodium tert-butoxide 10.5g (0.11mol), sodium ethoxide 7.4g (0.11mol) and tetrabutylammonium bromide, 1.6g (5mmol) was dissolved in 75mL of dichloromethane and stirred at room temperature after 0.5h, slowly dropwise inwardly bromohexanoate 0.1mol (17.8mL), after the completion of the dropwise addition, was refluxed at 35 9H, filtered, and the filtrate three times with saturated brine, dried over anhydrous sodium sulfate, minus 25 the organic phase was distilled to a pressure not drop out of the droplets, an oil, i.e. an intermediate compound .

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 7628 - 7633
Angew. Chem.,2018,vol. 130,p. 7754 - 7759,6
[2]Patent: CN110128364,2019,A .Location in patent: Paragraph 0066-0068; 0072-0074
[3]Journal of Medicinal Chemistry,1981,vol. 24,p. 1139 - 1148
[4]Patent: CN106749405,2017,A .Location in patent: Paragraph 0120; 0121

6
[ 19315-93-6 ]
[ 25542-62-5 ]
[ 87364-42-9 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: A solution of 6-hydroxy-3,4-dihydrocarbostyril (corresponding to 44) (2.00g, 12.26mmol) in DMF (10ml) was added dropwise to a suspension of NaH (60% in mineral oil, 0.59g, 14.71mmol) in DMF (5ml) for 14min at 0C with a CaCl2 tube. After stirring for 20min at 0C, a solution of 6-bromohexanoic acid ethyl ester (3.06g, 13.48mmol) in DMF (7ml) was added dropwise to the reaction mixture for 7min at 0C. The reaction mixture was stirred overnight, during which time the ice was allowed to gradually melt and was subsequently stirred for 3h at 110C. After cooling, H2O (100ml) was added to the mixture, and the resulting mixture was extracted with AcOEt (100ml×3). The combined organic layer was washed with H2O (100ml×1) and brine (100ml×1), dried over Na2SO4 (anhyd), filtered, and concentrated under reduced pressure. The crude product was purified through open silica gel column chromatography (n-hexane/AcOEt=1:2) to afford a colorless solid (2.56g, 8.38mmol, y. 68%).

Reference： [1]Chemical and Pharmaceutical Bulletin,1983,vol. 31,p. 852 - 860
[2]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 3720 - 3731

7
[ 25542-62-5 ]
[ 14173-30-9 ]
[ 99156-18-0 ]

Reference： [1]Farmaco, Edizione Scientifica,1985,vol. 40,p. 630 - 644
[2]Arzneimittel-Forschung/Drug Research,1986,vol. 36,p. 1561 - 1563

8
[ 25542-62-5 ]
[ 90-02-8 ]
[ 146940-58-1 ]

Yield	Reaction Conditions	Operation in experiment
98%	With potassium carbonate; In N,N-dimethyl-formamide; for 24h;Inert atmosphere; Reflux;	General procedeure: In a 250-mL round-bottom flask, 4-hydroxybenzaldehyde (5g, 41 mmol, 1eq.) and K2CO3( 14g,101 mmol, 2.5eq) were dissolved in anhydrous DMF (25 mL). Ethyl 6-bromohexanoate (13.7g, 61 mmol, 1.5 eq.) was slowly added to the solution under nitrogen atmosphere and refluxed for 2-4 h. Reaction was monitored by TLC. The solution was filtered over Celite 535, diluted with ethyl acetate (150 mL), and washed with brine (100 mLx2). The organic phase was dried over MgSO4, filtered, and concentrated. The crude product, a colorless oil (10.66 g, 40 mmol, 99%), was used without further purification.
97%	With caesium carbonate; In N,N-dimethyl acetamide; at 20 - 140℃;Microwave irradiation; Sealed tube;	Reactions were carried out in a Biotage Initiator 60 Microwave Reactor, employing the 20mL process-scale reactor vials. Thirteen (13) identical reactions at the 10 mmol scale were setup in parallel and processed in serial, as follows: All three (3) reagents and reaction solvent were added to the MW vial in the following sequence; (1) ethyl-bromo-hexanoate (1.77 mL), (2) salicylaldehyde (1.05 mL), (3) cesium carbonate (CS2CO3) (3.91 g) and (4) reaction solvent DMA (17.18 mL). Care was taken to dispense the N-N-dimethylacetamide (DMA) solvent in such a manner so as to wash down the vial walls of reactant or solid base. To each vial was added a magnetic stir bar and fitted with a crimp seal cap and adapter collar. The reactions were than process in the MW Reactor for 10 minutes (at temperature) at 140 C with mixing. Following standard ramp up, fixed hold time at temperature and cool down, samples were kept sealed at ambient temperature until the entire lot was processed. The reaction mixtures were combined and transferred to a 2L separatory funnel. Vial contents were washed with ethyl acetate (EtOAc), and a total EtOAc layer of about 800 mL was added. To this was added 800 mL of 1.0 N NaOH solution, and the two layers were vigorously shaken and mixed and then separated. The NaOH aqueous layer was back-extracted 3 x 250 mL with EtOAc, and all the organic layers were combined (about 750 mL) and washed with 800 mL of 1.0 M citric acid solution. The citric acid layer was again back extracted with EtOAc (3 x 250 mL), and the organic layers were again combined (about 1.5 L) and washed (3 x 500 mL) with brine (saturated NaCl), dried over sodium sulfate (Na2SO t) and concentrated to dryness in vacuo. Silica gel TLC (3: 1 Hexanes-EtOAc) Rf = 0.34 (product), Rf = 0.45, 0.25 (trace impurities). Theoretical yield = 13 x 2.64 g or 34.32 g (130 mmol). Isolation and Observed yield = 33.30 g, (33.30 g/34.32 g x 100) = 97%. NMR (, 13C, COSY) and LCMS (ESI+/-) conform to structure.
93.4%	With sodium carbonate; In N,N-dimethyl-formamide; at 80℃; for 3h;Inert atmosphere;	A solution of salicylaldehyde (5.0 g, 40.9 mmol) in DMF (50 mL) was treated with potassium carbonate (8.48 g, 61 mmol) and ethyl-6-bromo hexanoate (10.96 g, 49.4 mmol) at rt under nitrogen atmosphere. The resulting reaction mixture was heated at 80C with constant stirring for 3 h. The reaction mixture was cooled to rt and filtered and washed with ethyl acetate. The filtrate was concentrated underreduced pressure and residue obtained was diluted with cold water (50 mL), before extracting with ethyl acetate (200 mL). The organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography (elution, 10% EtOAc-hexanes) to afford the title compound (10.01 g, 93.4% yield). LCMS (m/z): 265.5 (M+1).

93.0%

With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 3h;Inert atmosphere;

In a 250 mL round bottom flask, a solution of salicylaldehyde (10 g, 81.96 mmol) in DMF (100 mL) was treated with K2C03 (17.12 g, 122.95 mmol) and <strong>[25542-62-5]ethyl 6-bromohexanoate</strong> (21.91 g, 98.36 mmol) at RT under nitrogen atmosphere. The resulting reaction mixture was heated at 80 C with constant stuffing for 3 h. The reaction mixture was cooled to RT, the solid was filtered and washed with EtOAc. The combined filtrate was concentrated under reduced pressure and residue obtained was diluted with cold water (100 mL), before extracting with EtOAc (400 mL). The organic layer was washed with brine, dried over anhydrous Na2504 and concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography (elution, 10% EtOAc in hexanes). Yield: 20.12 g (93.0% yield).LCMS (ESI+, m/z): 287.1 (M+Na)

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 4536 - 4539
[2]Patent: WO2014/165827,2014,A1 .Location in patent: Page/Page column 80; 81
[3]Patent: WO2016/57322,2016,A1 .Location in patent: Page/Page column 133
[4]Patent: WO2016/57658,2016,A1 .Location in patent: Page/Page column 63
[5]Chemische Berichte,1984,vol. 117,p. 2157 - 2192
[6]Archiv der Pharmazie,1992,vol. 325,p. 773 - 777

9
[ 25542-62-5 ]
[ 603-35-0 ]
(ω-carbethoxypentylidene)triphenylphosphonium bromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	In chloroform; at 80℃; for 48h;Inert atmosphere;	A solution of triphenylphosphine(7.9 g, 30.0 mmol) in CHCl3 (100 mL) was add to 8 (6.7 g, 30.0 mmol) and the reaction mixturewas magnetically stirred under nitrogen atmosphere at 80 C for 48 hours. Then the reactionmixture was cooled to room temperature and concentrated under reduced pressure. The mixturewas added diethyl ether (50 mL) and magnetically stirred. After 1 h, the supernatant liquid wasdecanted and this process was repeated once. The resulting viscous liquid was dried undervacuum to form 9 as a white foam (13.8 g, 95% yield). 1H-NMR (400 MHz, CDCl3) delta 1.15 (t,3H, J = 7.1 Hz), 1.53-1.65 (m, 6H), 2.25 (t, 2H, J = 7.1 Hz), 3.64-3.72 (m, 2H), 4.00 (q, 2H, J =7.1 Hz), 7.63-7.70 (m, 6H), 7.74-7.79 (m, 9H); 13C-NMR (100 MHz, CDCl3) delta 13.6, 21.6 (d, JPC= 4.3 Hz), 22.2, 23.6, 29.0 (d, JPC = 16.4 Hz), 33.0, 59.5, 117.4 (d, JPC = 85.3 Hz), 129.9 (d, JPC =12.2 Hz), 132.9 (d, JPC = 9.3 Hz), 134.5 (d, JPC = 2.6 Hz), 172.6; 31P-NMR (162 MHz, CDCl3) delta24.3 ; MS (FAB) for C26H30O2+: calc 405.2, found 405.2.
78%	In acetonitrile; at 20℃; for 7h;Reflux;	To a solution of triphenylphosphine (918 mg, 3.5 mmol) in MeCN (5 mL) was added 6-bromohexanoic acid ethyl ester (669 muL, 3.0 mmol). The mixture was refluxed for 7 h and concentrated. The residue was purified by silica gel column chromatography to give the target compound (1.14 g, 78%) as a white foam.1H NMR (500 MHz, CDCl3) delta: 7.89-7.85 (m, 6H), 7.81-7.78 (m, 3H), 7.72-7.68 (m, 6H), 4.07 (q, 2H, J = 7.3 Hz), 3.95-3.89 (m, 2H), 2.27 (t, 2H, J = 7.3 Hz), 1.76-1.72 (m, 2H), 1.66-1.58 (m, 4H), 1.22 (t, 3H, J = 7.3 Hz). FAB-MS m/z: 405 [M-Br]+.
36.7 g	In toluene; for 27h;Reflux;	20.4 g (91.4 mmol) of <strong>[25542-62-5]ethyl 6-bromohexanoate</strong> as a compound of the formula (2), 20.0 g (76.3 mmol) of triphenylphosphine and 38 ml of toluene were charged in a 200 ml round bottom flask, Was heated under reflux for 27 hours with stirring. After completion of the reaction, the organic layer was removed by decanting, the residue was washed with 100 ml of petroleum ether, and then the solvent was removed with a vacuum pump to obtain 36.7 g of the crude phosphonium salt of the formula (3).

Reference： [1]Synlett,2014,vol. 25,p. 2787 - 2790
[2]Chemical Communications,2017,vol. 53,p. 6327 - 6330
[3]Beilstein Journal of Organic Chemistry,2009,vol. 5
[4]Journal of Medicinal Chemistry,1995,vol. 38,p. 636 - 646
[5]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 3156 - 3172
[6]Patent: JP2016/124833,2016,A .Location in patent: Paragraph 0026-0028

10
[ 25542-62-5 ]
[ 1666-13-3 ]
ethyl 6-(phenylselanyl)hexanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With zinc; In N,N-dimethyl-formamide; at 100℃; for 2h;Inert atmosphere;	General procedure: Under argon atmosphere, to a mixture of diaryl diselenide (0.5mmol), zinc (52mg, 0.8mmol), and MCM-41-2N-RuCl3 (2mol%) were successively added DMF (3mL) and alky halide (1.2mmol). The mixture was stirred at 100C for 2h. The reaction mixture was cooled to room temperature and diluted with EtOAc (20mL) and filtered. The MCM-41-2N-RuCl3 catalyst was washed with diluted hydrochloric acid (2×5mL), distilled water (2×5mL), and EtOH (2×5mL) and reused in the next run. The filtrate was washed with brine (2×10mL), dried over MgSO4. After removal of the solvent under reduced pressure, the residue was purified by silica gel chromatography using light petroleum ether or light petroleum ether/ CH2Cl2 (ca. 10:1, v/v) as the eluent to afford the desired product 3.

Reference： [1]Tetrahedron,1995,vol. 51,p. 7959 - 7980
[2]Journal of Organometallic Chemistry,2017,vol. 840,p. 38 - 46

11
[ 40882-83-5 ]
[ 25542-62-5 ]
5,10,15,20-tetra[N-(ethylcarbonylpent-6-yl)pyridinium-3-yl]porphyrin tetrabromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	In N,N-dimethyl-formamide for 4h; Heating;

Reference： [1]Dancil, Keiki-Pua S.; Hilario, Lynn F.; Khoury, Richard G.; Mai, Kim U.; Nguyen, Chi K.; Weddle, Katherine S.; Shachter, Amy M. [Journal of Heterocyclic Chemistry, 1997, vol. 34, # 3, p. 749 - 755]

12
[ 25542-62-5 ]
[ 16834-13-2 ]
5,10,15,20-tetrakis(1-(6-ethoxy-6-oxohexyl)-4-pyridin-1-io)-21H,23H-porphyrin tetrabromide [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,1997,vol. 34,p. 749 - 755

13
[ 25542-62-5 ]
[ 19812-93-2 ]
[ 144529-78-2 ]

Yield	Reaction Conditions	Operation in experiment
67.84%	With potassium carbonate; In N,N-dimethyl-formamide; at 90℃; for 24h;	As it is shown in the following schemes 1, 4-cyano-4'-hydroxy-biphenyl (4-cyano-4'-hydroxybiphenyl, 4.105 g, 21.05 mmol) and ethyl 6-bromo-hexanoate (ethyl-6-bromohexanoate, 4.9 g, 21.96 mmol) and Anhydrous calcium carbonate (anhydrouspotassiumcarbonate,K2CO3,2.91g,21.05The mmol)RefinedN, N- dimethyl methane amide (N, N-dimethylmethanamide, is added to 30 mL).And refluxed at 90 for 24 hours.After the reaction, remove all the solvent,Ethyl acetate (ethyl acetate, EA) to melt and wash with distilled water.The organic layer is MgSO4Dried with.Recrystallized with ethanolThe filter then forward (yield: 67.84%, 4.81 g).We confirmed the 2-ethyl hexanoate acid ester of the (4-cyano-4'-by-phenoxy) prepared by NMR, the results 1[0121]The it exhibited.1H NMR (CDCl3): delta =1.18-1.21 (t; 3H), 2.45 (m; 2H), 1.63-1.64 (m; 2H), 1.74-1.76 (m; 2H) 2.25-2.29 (t;[0122]2H), 3.92-4.07 (t; 2H), 4.05-4.07 (t; 2H), 6.89-6.92 (d; 2H), 7.44-7.46 (d; 2H), 7.57-7.60 (d; 4H)

Reference： [1]Soft Matter,2010,vol. 6,p. 1958 - 1963
[2]Macromolecules,2004,vol. 37,p. 3569 - 3575
[3]Journal of the American Chemical Society,2008,vol. 130,p. 1735 - 1740
[4]Organic Letters,2015,vol. 17,p. 3244 - 3247
[5]Patent: KR101575025,2015,B1 .Location in patent: Paragraph 0118 - 0123
[6]Journal of Materials Chemistry,1997,vol. 7,p. 2001 - 2011
[7]Chemistry Letters,2010,vol. 39,p. 170 - 171
[8]RSC Advances,2016,vol. 6,p. 81902 - 81912

14
[ 25542-62-5 ]
[ 66943-05-3 ]
[ 1025897-57-7 ]

Reference： [1]Russian Chemical Bulletin,1999,vol. 48,p. 1950 - 1959
[2]Journal of the Chemical Society. Perkin Transactions 2 (2001),2000,p. 563 - 570

15
[ 611-08-5 ]
[ 25542-62-5 ]
[ 459141-79-8 ]

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 3630 - 3638

16
[ 25542-62-5 ]
[ 24155-42-8 ]
6-[1-(2,4-dichloro-phenyl)-2-imidazol-1-yl-ethoxy]-hexanoic acid ethyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2002,vol. 10,p. 3707 - 3711

17
[ 25542-62-5 ]
[ 35692-27-4 ]
ethyl 6-(4-methoxyphenyl)hexanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With methyldi-t-butylphosphine; tetrabutyl ammonium fluoride; palladium(II) bromide In tetrahydrofuran at 20℃; for 14h;

Reference： [1]Lee, Jae-Young; Fu, Gregory C. [Journal of the American Chemical Society, 2003, vol. 125, # 19, p. 5616 - 5617]

18
[ 25542-62-5 ]
[ 138034-95-4 ]
(Z)-10-Phenyl-dec-7-enoic acid ethyl ester [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2003,vol. 42,p. 5079 - 5082
[2]Journal of the American Chemical Society,2003,vol. 125,p. 3718 - 3719

19
[ 25542-62-5 ]
[ 15485-80-0 ]
[ 640275-83-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2003,vol. 11,p. 4069 - 4081

20
[ 25542-62-5 ]
[ 3681-99-0 ]
7-O-[5-(ethoxycarbonyl)pentyl]puerarin [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2003,vol. 11,p. 4069 - 4081

21
[ 25542-62-5 ]
[ 628-91-1 ]
[ 123-29-5 ]

Reference： [1]Angewandte Chemie - International Edition,2004,vol. 43,p. 6180 - 6182

22
[ 56-04-2 ]
[ 25542-62-5 ]
[ 912956-60-6 ]

Yield	Reaction Conditions	Operation in experiment
40%	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h;
	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h;

Reference： [1]Mai, Antonello; Massa, Silvio; Rotili, Dante; Simeoni, Silvia; Ragno, Rino; Botta, Giorgia; Nebbioso, Angela; Miceli, Marco; Altucci, Lucia; Brosch, Gerald [Journal of Medicinal Chemistry, 2006, vol. 49, # 20, p. 6046 - 6056]
[2]Mai, Antonello; Massa, Silvio; Rotili, Dante; Pezzi, Riccardo; Bottoni, Patrizia; Scatena, Roberto; Meraner, Joachim; Brosch, Gerald [Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 21, p. 4656 - 4661]

23
[ 51-52-5 ]
[ 25542-62-5 ]
[ 912956-61-7 ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 6046 - 6056
[2]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 4656 - 4661

24
[ 36822-11-4 ]
[ 25542-62-5 ]
6-(6-oxo-4-phenyl-1,6-dihydro-pyrimidin-2-ylsulfanyl)-hexanoic acid ethyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 6046 - 6056
[2]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 4656 - 4661

25
[ 25542-62-5 ]
[ 141-90-2 ]
[ 912956-59-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 4656 - 4661

26
[ 56-04-2 ]
[ 25542-62-5 ]
[ 912956-60-6 ]

Yield	Reaction Conditions	Operation in experiment
70%	With sodium ethanolate In ethanol at 0 - 80℃; for 2.5h;

Reference： [1]Brun, Eva M.; Garces-Garcia, Marta; Escuin, Estefania; Morais, Sergi; Puchades, Rosa; Maquieira, Angel [Environmental Science and Technology, 2004, vol. 38, # 4, p. 1115 - 1123]

27
[ 25542-62-5 ]
[ 7217-59-6 ]
6-(2-methoxy-phenylsulfanyl)-hexanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%		Example 3 - Preparation of 6-(2-Methoxy-phenylsulfanyl)-hexanoic acid (Compound 3); [96] To a 500 mL flask, equipped with a magnetic stir bar, was added ethyl 6-bromo- hexanoate (12.0 mL, 67 mmol), 2-methoxybenzenethiol (8,2 mL, 67 mmol), and 52 mL ethyl alcohol. The reaction vessel was cooled with an external ice bath while potassium hydroxide (7.72 g, 138 mmol) was added. The reaction was allowed to stir at room temperature for 18 hours under nitrogen atmosphere. Water (100 mL) and 50 mL of aqueous 1 N sodium hydroxide solution were added and the mixture allowed to stir at room temperature for 18 hours. Ethyl alcohol was distilled at atmospheric pressure. The resulting solution was acidified to pH 1 with aqueous 1 N hydrochloric acid and cooled to 4C for 18 hours. The product (16.3 g, 95%) was isolated by filtration as an off-white powder, mp 81-820C. Found: C: 60.70 %, H: 7.08 % S:SUBSTITUTE SHEET (RULE 26) <n="39"/>12.46 %; C13Hi8O3S requires C: 60.87 %, H: 7.17 %, S: 12.50 %; IH NMR (d6-DMSO): 512.0, broad s, IH (COOH); delta 7.20, dd, IH (aryl H); delta 7.16, dt, IH (aryl H); delta 6.96, dd, IH (aryl H); delta 6.93, dt, IH (aryl H); delta 3.80, s, 3H (OCH3); delta 2.86, t, 2H (CH2 alpha to S); 6 2.20, t, 2H (CH2 alpha to COOH); delta 1.6-1.3, multiplet, 6H (rest of CH2's).

Reference： [1]Patent: WO2008/14430,2008,A1 .Location in patent: Page/Page column 37-38

28
[ 25542-62-5 ]
[ 65374-10-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium azide; In methanol; water;	EXAMPLE 169 2-(5-Aminopentyl)-5-carboxamido-1,4-dihydro-6-methyl-4-(4-nitrophenyl)-3-{N-[3-(4,4-diphenylpiperidin-1-yl)prop-yl]carbozamidopyridine (169) A solution of <strong>[25542-62-5]ethyl 6-bromohexanoate</strong> (10.0 g, 44.8 mmol), NaN3 (5.83 g, 89.6 mmol) and 25 ml of water in 75 ml of MeOH was refluxed for 3.5 hrs. The MeOH was removed in vacuo and the residue was partitioned between CHCl3 (200 ml) and water (50 ml). The organic layer was separated and washed with water. After drying (Na2 SO4) and evaporation of solvent, ethyl 6-azidohexanoate (8.59 g, 100%) was obtained as a colorless oil.
	With sodium azide; In N,N-dimethyl-formamide; at 20 - 80℃;	General Procedure 1: Preparation of Azides from Aliphatic BromidesAt RT, excess sodium azide (about 4-6 eq.) is added to a solution of the appropriate bromide in DMF (about 0.2 to 1 mol/l). The suspension is stirred vigorously at 50-80 C. for 2-18 h. After cooling to RT, the reaction mixture is diluted (for example with ethyl acetate or dichloromethane) and washed successively with saturated sodium bicarbonate solution and saturated sodium chloride solution. After careful concentration under reduced pressure, the crude product may, if required, be purified by chromatography on silica gel (typical mobile phase mixture, for example, cyclohexane/ethyl acetate 100:1 to 10:1).
	With sodium azide; In N,N-dimethyl-formamide; at 80℃;	Ethyl 6-bromohexanoate (1 eq) was dissolved in DMF,Sodium azide (3 eq) was added,The temperature was slowly raised from room temperature to 80 C and the reaction was carried out at that temperature overnight.After the addition of ethyl acetate, the excess sodium azide was removed by filtration, water was added and extracted with ethyl acetate.The organic phase was washed with water, saturated brine and dried over anhydrous sodium sulfate.Filtration and removal of the solvent using a rotary evaporator gave the title compound

Reference： [1]Patent: US5767131,1998,A
[2]Tetrahedron,2007,vol. 63,p. 9007 - 9015
[3]Organic Letters,2011,vol. 13,p. 2754 - 2757
[4]Patent: US2012/28971,2012,A1 .Location in patent: Page/Page column 15
[5]Chinese Journal of Chemistry,2014,vol. 32,p. 157 - 162
[6]Chemical Communications,2015,vol. 51,p. 16312 - 16315
[7]European Journal of Medicinal Chemistry,2017,vol. 127,p. 900 - 908
[8]Patent: CN106883217,2017,A .Location in patent: Paragraph 0103; 0104; 0105; 0106

29
[ 3017-69-4 ]
[ 25542-62-5 ]
ethyl 8-methyl-7-nonenoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	Stage #1: 2-methyl-1-propenylbromide With magnesium In tetrahydrofuran Stage #2: 6-bromo-hexanoic acid ethyl ester With N,N,N,N,-tetramethylethylenediamine; hexamethylenetetramine In tetrahydrofuran at 0℃; for 1.5h; Further stages.;

Reference： [1]Cahiez, Gerard; Duplais, Christophe; Moyeux, Alban [Organic Letters, 2007, vol. 9, # 17, p. 3253 - 3254]

30
[ 25542-62-5 ]
[ 64019-57-4 ]
triethyl 6,6',6"-(2,2',2"-nitrilotris(methylene)tris(1H-benzimidazole-2,1-diyl))trihexanoate [ No CAS ]
diethyl 6,6'-(2,2'-((1H-benzo[d]imidazol-2-yl)methylazanediyl)bis(methylene)-bis(1H-benzimidazole-2,1-diyl))dihexanoate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 12696 - 12704

31
[ 25542-62-5 ]
[ 3380-34-5 ]
ethyl 6-[5-chloro-2-(2,4-dichlorophenoxy)phenoxy]hexanoate [ No CAS ]

Reference： [1]Journal of Agricultural and Food Chemistry,2007,vol. 55,p. 3758 - 3763

32
[ 25542-62-5 ]
[ 50592-87-5 ]

Reference： [1]Journal of the Indian Chemical Society,1942,vol. 19,p. 305

33
[ 25542-62-5 ]
[ 123-08-0 ]
[ 156060-77-4 ]

Yield	Reaction Conditions	Operation in experiment
99%	With potassium carbonate; In N,N-dimethyl-formamide; for 24h;Inert atmosphere; Reflux;	General procedeure: In a 250-mL round-bottom flask, 4-hydroxybenzaldehyde (5g, 41 mmol, 1eq.) and K2CO3( 14g,101 mmol, 2.5eq) were dissolved in anhydrous DMF (25 mL). Ethyl 6-bromohexanoate (13.7g, 61 mmol, 1.5 eq.) was slowly added to the solution under nitrogen atmosphere and refluxed for 2-4 h. Reaction was monitored by TLC. The solution was filtered over Celite 535, diluted with ethyl acetate (150 mL), and washed with brine (100 mLx2). The organic phase was dried over MgSO4, filtered, and concentrated. The crude product, a colorless oil (10.66 g, 40 mmol, 99%), was used without further purification.
95%	With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 50℃; for 20h;	A mixture of 4-hydroxybenzaldehyde 1 (3, 0.60 kg, 4.91 mol), ethyl-6-bromohexanoate 2 (4, 1.10 kg, 4.91 mol), and K2CO3 (1.36 kg, 9.83 mol) in DMF (2 L) was stirred at 50 C. for 20 h. The mixture was filtered to remove remaining K2CO3. The resulting solution was concentrated in vacuo, diluted with EtOAc (3 L) and subsequently washed with saturated aqueous NaCl (3×1.5 L). The organic layer was dried (MgSO4), filtered and concentrated in vacuo to give an off white solid (3, 1.23 kg, 4.66 mol, 95%) with no need for further purification: M.p.: 33-35 C. 1H NMR (400 MHz, CDCl3) delta=9.87 (s, 1H), 7.81 (d, J =8.7, 2H), 6.97 (d, J=8.7, 2H), 4.12 (q, J=7.1, 2H), 4.04 (t, J=6.4, 2H), 2.33 (t, J=7.4, 2H), 1.82 (m, 2H), 1.69 (m, 2H), 1.53 (m, 2H), 1.25 (t, J=7.1, 3H); 13C NMR (400 MHz, CDCl3) delta=191.0, 173.7, 164.3, 132.1 (2C), 130.1, 114.9 (2C), 68.3, 60.5, 34.4, 29.0, 25.8, 24.8, 14.4; IR (film) nu=2941, 1719, 1688, 1595, 1579, 1509, 1466, 1392, 1307, 1252, 1213, 1155, 1108, 1030, 999, 832 cm-1; HRMS (MALDI-FTMS) m/z 287.1254 (287.1254 calculated for C15H20O4Na, (M+Na)+).
	With potassium carbonate; In acetonitrile; at 80℃; for 24h;	General procedure: 4-hydroxybenzaldehyde(13b)(1.22g,10 mmol) and ethyl 5-bromopentanoate(2.09g, 10mmol)were dissolved in acetonitrile (100 mL) and treated with K2CO3 (5.52 g, 40mmol).The reaction mixture was stirred at 80 C for 24 h.Water was added tothereaction,and the aqueous layer was extracted with EA (3 × 20 mL). Theorganic layers were combined, washed with water (3 × 25 mL),dried overanhydrous Na2SO4, and concentrated in vacuo to give compound 14aa (1.82g, 73%).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 4536 - 4539
[2]Inorganic Chemistry,2015,vol. 54,p. 7368 - 7380
[3]Patent: US2003/225205,2003,A1 .Location in patent: Page 14
[4]Tetrahedron Letters,2013,vol. 54,p. 1869 - 1872
[5]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 4051 - 4055
[6]RSC Advances,2018,vol. 8,p. 20087 - 20094

34
[ 25542-62-5 ]
[ 835-11-0 ]
[ 870287-15-3 ]

Yield	Reaction Conditions	Operation in experiment
27%		(Compound 160) 6-(2-(2-Hydroxybenzoyl)phenoxy)hexanoic acid:; A 250 mL round bottom flask equipped with a magnetic stirrer bar and a reflux condenser was charged with 10.32 g (48.2 mmol) of <strong>[835-11-0]2,2'-dihydroxybenzophenone</strong> and 100 mL of dimethylsulfoxide (DMSO). Potassium hydroxide (2.91 g, 51.9 mmol) that had been ground to a powder was added to the clear solution. The reaction mixture was heated to 45C, until most of the solid had dissolved. The resulting red slurry was treated with 8.80 mL (11.04 g, 49.5 mmol) of ethyl 6-bromohexanoate. After stirring for 20 hr at 25C, the clear reaction mixture was diluted with aqueous 1 % hydrochloric acid and methyl t-butyl ether (MTBE). The layers were separated. The organic phase was washed with water (2 X 50 mL) and brine (1 X 40 ML), dried over sodium sulfate and concentrated. The residue was taken up in 100 mL of tetrahydrofuran (THF) and treated with potassium trimethylsilanoate (15.09 g, 118 mmol). The orange solution was stirred for 20 hr at 25C, diluted with aqueous 4% hydrochloric acid to pH 7.5 and washed with MTBE. The organic phase was extracted with aqueous 3% sodium bicarbonate solution. The combined aqueous phases were acidified to pH 2 with aqueous 4% hydrochloric acid and extracted with 60 mL of MTBE. This organic phase was washed with brine (1 X 40 mL), dried over sodium sulfate and concentrated. The residue was purified by flash chromatography using 80% hexanes/ethyl acetate (spiked with 0.5% acetic acid). The product (4.2 g, 27 %) was isolated as an off-white solid, mp 89-91C. Combustion analysis: Found: C 69.50, H 6.04%; C19H20O5 requires C: 69.50, H: 6.14 % 1H NMR (d6-DMSO): 6 12.0, bs, 1H (COOH) ; No. 11.5, bs, 1H (OH); 6 7.5, t, 2H, (arylH's); 6 7.4, dd, 1H (arylH) ; 6 7.3, dd, 1H (arylH) ; No. 7.15, d, 1H (arylH) ; 6 7.1, t, 1H (arylH) ; No. 7.0, d, 1H (arylH) ; 6 6.9, t, 1H (arylH);6 3.9, t, 2H, (CH2 a to 0); No. 2.05, t, 2H (CH2 a to COOH); No. 1.4, m, 4H (other two CHz's); No.1.0, p, 2H (CH2 in middle of chain).

Reference： [1]Patent: WO2005/112633,2005,A2 .Location in patent: Page/Page column 90

35
[ 86-79-3 ]
[ 25542-62-5 ]
ethyl 6-(9H-carbazol-2-yloxy)-hexanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33%	With potassium carbonate; In water; N,N-dimethyl-formamide;	(a) <strong>[86-79-3]2-Hydroxycarbazole</strong> (0.5 g, 2.7 mmol), ethyl 6-bromohexanoate (0.6 g, 2.7 mmol), and potassium carbonate (0.4 g, 3.0 mmol) in dimethyl formamide (10 ml) were heated to 120 C. for 24 h. Water was added and extraction with ethyl acetate was performed. The combined organic phases were washed with water and dried (sodium sulfate). The solvent was removed i.vac. and the residue was purified by column chromatography (silica gel, ethyl acetate:heptane=1:1) to give ethyl 6-(9H-carbazol-2-yloxy)-hexanoate (290 mg, 33%) as a colorless solid. MS (M-H+) 324.

Reference： [1]Patent: US2002/183513,2002,A1

36
[ 609-14-3 ]
[ 25542-62-5 ]
[ 407627-95-6 ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium tert-butylate; In ethyl acetate; tert-butyl alcohol;	Example 9 Synthesis of 3-[3-(5-carboxypentyl)-5-iodo-2,3-dimethyl-3H-1-indoliumyl]-1-propanesulfonate (2) A mixture of 13.4 g (0.12 mol) of potassium tert-butoxide and 100 g of tert-butanol was stirred and heated until the tert-butoxide totally dissolved. The solution was cooled to about 50 C. and 17 g (0.12 mmol) of ethyl 2-methylacetoacetate was added dropwise. Ethyl-6-bromohexanoate (30 g, 0.13 mmol) was then added dropwise and the reaction mixture was stirred and refluxed for 5 hours. The mixture was filtered and the solvent was removed under reduced pressure. The residue was partitioned between 1M HCl and chloroform. The organic layer was dried over magnesium sulfate and purified on silica gel using 1:10 ethyl acetate/hexane as the eluent to yield 25 g (75%) of diethyl 2-acetyl-2-methyloctanedioate (3) as yellow liquid.
75%	With potassium tert-butylate; In tert-butyl alcohol; at 50℃; for 5h;Reflux;	A mixture of 13.4 g (0.12 mol) of potassium tert-butoxide and 100 g of tert-butanol was stirred and heated until the tert-butoxide totally dissolved. The solution was cooled to about 50 C. and 17 g (0.12 mmol) of ethyl 2-methylacetoacetate was added dropwise. Ethyl-6-bromohexanoate (30 g, 0.13 mmol) was then added dropwise and the reaction mixture was stirred and refluxed for 5 hours. The mixture was filtered and the solvent was removed under reduced pressure. The residue was partitioned between 1M HCl and chloroform. The organic layer was dried over magnesium sulfate and purified on silica gel using 1:10 ethyl acetate/hexane as the eluent to yield 25 g (75%) of diethyl 2-acetyl-2-methyloctanedioate (3) as yellow liquid.
63.4%	With sodium ethanolate; In ethanol; at 120℃; for 12h;	Example 9.1 (0321) (0322) Ethyl 2-methyl acetoacetate (29.2 mL, 0.203 mol. 1 eq), 21% sodium ethoride solution (64 mL, 0.816 mol, 4 eq), <strong>[25542-62-5]ethyl 6-bromohexanoate</strong> (34 mL, 0.192 mol, 1 eq) and ethanol (200 mL) are added and the mixture is subjected to reflux at 120 C. for 12 hours. Next, the solvent is neutralized with 1M hydrochloric acid and extraction is carried out by using chloroform and distilled water. The extracted solvent is dried under reduced pressure and purification is carried out by normal phase chromatography to obtain the target compound (36.8 g, 63.4%). (0323) Rf=0.34 (Silica gel, hexane/ethyl acetate=10:1 v/v)

	With sodium ethanolate; In ethanol; ethyl acetate;	EXAMPLE 1 Preparation of 3-(5-carboxypentyl)-2,3-dimethyl-5-sulfoindolium, Inner Salt (Compound 1) A mixture of 25 g of ethyl 2-methylacetoacetate, 64 mL of a 21% sodium ethoxide solution in ethanol and 34 mL of <strong>[25542-62-5]ethyl 6-bromohexanoate</strong> is refluxed in 200 mL of ethanol overnight. The mixture is filtered and solvent is evaporated. The residue is partitioned between 1 M HCl and chloroform. The organic layer is dried over magnesium sulfate and purified on silica gel using 1:10 ethyl acetate/ hexanes as eluant to yield 22 g of ethyl 2-(5-carbethoxypentyl)-2-methylacetoacetate. The acetoacetate thus obtained is dissolved in 300 mL of methanol.
22 g	With sodium ethanolate; In ethanol;Reflux;	10103] A mixture of 25 g of ethyl 2-methylacetoacetate, 64 mL of a 21% sodium ethoxide solution in ethanol and 34 mL of <strong>[25542-62-5]ethyl 6-bromohexanoate</strong> is refluxed in 200 mL of ethanol overnight. The mixture is filtered and solvent is evaporated. The residue is partitioned between 1 M HC1 and chloroform. The organic layer is dried over magnesium sulfate and purified on silica gel using 1:10 ethyl acetate/hexanes as eluant to yield 22 g of ethyl 2-(5-carbethoxypentyl)-2-methylacetoac- etate.
15 g	With sodium ethanolate; In ethanol; for 12h;Reflux;	To the solution of sodium ethoxide (173.4 mmol, prepared from 4.0 g sodium in 200 mL dry ethanol) is added ethyl 2-methylacetoacetate (25.0 g, 173.4 mmol), followed by ethyl 6-bromohexanonate (44.5 g, 190.7 mmol). The mixture is heated to reflux for 12 hours. After cooling to room temperature, the mixture is filtered and the filtrate is concentrated. The residue is treated with 1M HCl to pH 1 and the aqueous solution is extracted with chloroform twice. The organic layer is washed with brine and dried over Na2SO4. After removal of solvent, the residue is purified on silica gel to afford 15 g ethyl 2-(5-ethoxycarbonyl)pentyl-2-methylacetoacetate.
	With sodium ethanolate; In ethanol; for 48h;Reflux;	To prepare compound 1, shown below, to the solution of sodium ethoxide (40 g sodium in 500 mL dry ethanol) was added ethyl 2-methylacetoacetate (250 g), followed by ethyl 6-bromohexanonate (445 g). The mixture was heated to reflux for 2 days. After cooling to room temperature, the mixture was filtered and the filtrate was concentrated. The residue was treated with 1M HCl to pH 1 and the aqueous solution was extracted with chloroform twice. The organic layer was washed with brine and dried over Na2SO4. After removal of solvent, the residue was purified on silica gel to give ethyl 2-(5-ethoxycarbonyl)pentyl-2-methylacetoacetate.
47.7 g	With sodium ethanolate; In ethanol; at 80℃; for 10h;	The compound represented by Formula 8-a was synthesized by Reaction 8-1.Ethyl 2-methylacetatoacetate (23.5 g, 163 mmol) and <strong>[25542-62-5]ethyl 6-bromohexanoate</strong> (40.0 g, 179 mmol) were stirred in 200 ml of ethanol and liquid sodium ethoxide was added dropwise thereto. The mixture was stirred at 80 C. for 10 h. After completion of the reaction, the solid was filtered off. The filtrate was distilled under reduced pressure and extracted with dichloromethane and a 2 N aqueous solution of hydrochloric acid. The organic layer was treated with anhydrous sodium sulfate and distilled under reduced pressure (47.7 g). After removal of the solvent, 300 ml of water was added, followed by stirring under reflux for 10 h. After completion of the reaction, the reaction solution was extracted with dichloromethane, treated with sodium sulfate, and distilled under reduced pressure (25 g, 71%).1H NMR (400 MHz, CDCl3): delta=10.85 (1H, s), 2.52 (1H, m), 2.36 (2H, m) 2.30 (3H, s), 1.65 (4H, m), 1.35 (4H, m), 1.09 (3H, d)

Reference： [1]Patent: US2013/231604,2013,A1 .Location in patent: Page/Page column
[2]Patent: US8748446,2014,B2 .Location in patent: Page/Page column 109; 110
[3]Patent: US2017/313883,2017,A1 .Location in patent: Paragraph 0321; 0322; 0323
[4]Patent: US2002/77487,2002,A1
[5]Patent: US2015/218380,2015,A1 .Location in patent: Paragraph 0103
[6]Patent: US2015/259535,2015,A1 .Location in patent: Paragraph 0092
[7]Patent: US9289515,2016,B2 .Location in patent: Page/Page column 12
[8]Patent: US10473666,2019,B2 .Location in patent: Page/Page column 52-53

37
[ 25542-62-5 ]
[ 886548-37-4 ]

Yield	Reaction Conditions	Operation in experiment
85%		Cyanoindole ( 500 mg, 3.52 mrnol ) was added to a suspension of sodium iydride (1.1 eq. 148 mg of 60% dispersion in mineral oil) in dimethylformaniide and the reaction was stirred for 10 min. Then <strong>[25542-62-5]ethyl 6-bromohexanoate</strong> (1.5 eq, 1.18 g, 5.28 mmol ) was added dropwise. The reaction was stirred at ambient temperature for 5 hours. Then water (8 :1) added and this was extracted with ethyl acetate. The ethyl acetate solution was concentrated in vacio and the residue was purified by silica gel column using ethyl acetate/ hexane as an eluting solvent to afford ethyl 6-(5-cyano-lH-indol-l-yl)he>canoate (850 mg, 85% yield). IH NMR (300 MHz, d6-DMSO): delta 8.057(d, J=I.172 HEz3 IH)5 EPO <DP n="36"/>7.65(d, J=8.793 Hz, IH), 7.6(d, J=2.93 Hz, IH), 7.5(dd, J=I.759Hz, 8.79Hz, IH), 6.6(d, J=3.5 Hz, IH), 4.2(t, J=7.03 Hz, 2H), 3.98(q, J=7.034 Hz, 2H), 2.2(t, J=7.3, 2H), 1.72(pent, J=7.62 Hz, 2H), 1.5 (pent, J=7.62 Hz, 2H), 1.2( m, 2H), 1.1 (t, J=7.034 Hz, 3H).
85%		EXAMPLE 26; ethyl 6-{5-cyarto-1H-indol-1-yi)hexanoate; [00233] Cyanoi?dole ( 500 mg, 3.52 mmol ) was added to a suspension of sodium hydride (1.1 eq. 148 mg of 60% dispersion m mineral oii) in dimethylformamide and the reaction was stirred for 10 min. Then <strong>[25542-62-5]ethyl 6-bromohexanoate</strong> (1 5 eq, 1.18 g, 5.28 mmol ) was added dropwsse. The reaction was stirred at ambient temperature for 5 hours. Then water (8 :1) added and this was extracted with ethyl acetate. The ethyl acetate solution was concentrated in vacio and the residue was purified by silica gel column using ethyl acetate/ hexane as an eluting solvent to afford ethyl 6-{5-cyano~1 H-indol-1- yl)bexanoate (850 mg, 85% yield). 1H NMR {300 MHz, d6-DMSO): delta 8.057(d, J=1.172 Hz1 1H), 7.65(d. J=8.793 Hz. 1H), 7.6(d, J=2.93 Hz, 1H), 7.5(dd, J=1.759Hz, 8.79Hz, 1H), 6.6(d, J=3,5 Hz, 1H), 4.2(t, J=7.03 Hz, 2H), 3.98{q, J=7.034 Hz, 2H), 2.2(t, J=7.3, 2H)1 1.72(pent, J=7.62 Hz, 2H), 1.5(pe?t, J=7.62 Hz, 2H), 1.2( m, 2H)1 1.1(1, J=7.034 Hz, 3H).

Reference： [1]Patent: WO2006/50236,2006,A2 .Location in patent: Page 34; 35
[2]Patent: WO2007/134169,2007,A2 .Location in patent: Page/Page column 70

38
[ 25542-62-5 ]
[ 619-08-9 ]
[ 1093799-04-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium carbonate; In N,N-dimethyl acetamide; at 60℃; for 16h;	A mixture of <strong>[619-08-9]2-chloro-4-nitrophenol</strong> (0.05 mol), 6-bromohexanoic acid, ethyl ester (0.055 mol) and K2CO3 (0.055 mol) in DMA (50 ml) was stirred for 16 hours at 60 C. The mixture was cooled. H2O was added. This mixture was extracted with EtOAc (3x). The combined organic layers were washed with water (2x), then dried (MgSO4), filtered and the solvent was evaporated. Yield: 15.8 g of intermediate 78 (quantitative yield; used in next reaction step, without further purification).

Reference： [1]Patent: WO2008/155421,2008,A2 .Location in patent: Page/Page column 76

39
[ 40314-06-5 ]
[ 25542-62-5 ]
[ 1001338-14-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium carbonate; In N,N-dimethyl-formamide; at 120℃; for 24h;	he starting materials were <strong>[40314-06-5]5-methyl-phthalimide</strong> (300 mg, 1.86 mmol) and K2CO3 (257.39 mg, 1.86 mmol), in 2 mL of DMF. 6-bromoethyl hexanoate (0.33 mL, 1.86 mmol) was added to this solution, and the reaction mixture was heated at 120ºC for 24 hours. After the reaction time elapsed, it is diluted with water and an extraction with ethyl acetate (3x5mL) was performed, the organic phase was dried on MgSO4, filtered and concentrated in the rotary evaporator. A yellow liquid was obtained (564 mg, quantitative yield). 1H-NMR (C3D6O): delta 7.70 (d, 1 H, Harom, J = 7.8 Hz); 7.61 (d, 2H, Harom, J = 8.4 Hz); 4.03 (c, 2H, O-CH2CH3, J = 7.1 Hz); 3.61 (t, 2H, N-CH2, J = 7.1 Hz); 2.50 (s, 3H, Ar-CH3); 2.26 (t, 2H, CH2-CO, J = 7.4 Hz); 1.70 - 1.57 (m, 4H, CH2); 1.40 - 1.32 (m, 2H, CH2); 1.16 (t, 3H, O-CH2CH3, J = 7.2 Hz). 13C-NMR (C3D6O): 172.7 (COOEt); 168.1 (CO); 168.0 (CO); 145.4 (Carom); 134.5 (CHarom); 132.8 (Carom); 129.8 (Carom); 123.4 (CHarom); 122.8 (CHarom); 59.6 (O-CH2CH3); 37.4 (N-CH2); 33.6 (CH2-CO); 28.1 (CH2); 26.1 (CH2); 24.4 (CH2); 21.0 (Ar-CH3); 13.7 (O-CH2CH3). HR LSIMS: Calculated for C17H21NO4Na (M+Na)+ 326.1368; found 326.1371 (deviation -0.9 ppm).

Reference： [1]Patent: EP2045239,2009,A1 .Location in patent: Page/Page column 14

40
[ 25542-62-5 ]
[ 177429-27-5 ]
[ 1133461-67-2 ]

Yield	Reaction Conditions	Operation in experiment
100%		Step 9b: Ethyl 4-(benzyloxy)-3-(6-ethoxy-6-oxohexyloxy)benzoate (Compound 503-16) The title compound 503-16 (6.7 g, 100%) was prepared as a yellowish oil from 502 (4.43 g, 16.3 mmol), ethyl 6-bromohexanoate (4.36 g, 19.5 mmol) using a procedure similar to that described for compound 307-9 (Example 3): LCMS: 437 [M+23]+; 1H NMR (DMSO-d6): delta 7.53 (d, J=8.4 Hz, 1H), 7.44-7.31 (m, 6H), 7.14 (d, J=8.4 Hz, 1H), 5.17 (s, 2H), 4.25 (q, J=7.2 Hz, 2H), 4.04-3.98 (m, 4H), 2.26 (t, J=6.9 Hz, 2H), 1.74-1.65 (m, 2H), 1.59-1.52 (m, 2H), 1.46-1.36 (m, 2H), 1.28 (t, J=6.9 Hz, 3H), 1.14 (t, J=7.2 Hz, 3H).
100%		Step 11a: Ethyl 4-(benzyloxy)-3-(6-ethoxy-6-oxohexyloxy)benzoate (compound 503-19) The title compound 503-19 (6.7 g, 100%) was prepared as a yellow oil from compound 502 (4.43 g, 16.3 mmol) and ethyl 6-bromohexanoate (4.36 g, 19.5 mmol) using a procedure similar to that described for compound 503-18 (Example 10): LCMS: 437 [M+23]+; 1H NMR (DMSO-d6): delta 7.53 (d, J=8.4 Hz, 1H), 7.44-7.31 (m, 6H), 7.14 (d, J=8.4 Hz, 1H), 5.17 (s, 2H), 4.25 (q, J=7.2 Hz, 2H), 4.04-3.98 (m, 4H), 2.26 (t, J=6.9 Hz, 2H), 1.74-1.65 (m, 2H), 1.59-1.52 (m, 2H), 1.46-1.36 (m, 2H), 1.28 (t, J=6.9 Hz, 3H), 1.14 (t, J=7.2 Hz, 3H).

Reference： [1]Patent: US2009/76044,2009,A1 .Location in patent: Page/Page column 30
[2]Patent: US2009/76044,2009,A1 .Location in patent: Page/Page column 32

41
[ 25542-62-5 ]
[ 704-13-2 ]
[ 1207268-48-1 ]

Yield	Reaction Conditions	Operation in experiment
67%	With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 12h;	To a solution of <strong>[704-13-2]3-hydroxy-4-nitrobenzaldehyde</strong> (0.80 g, 4.78 mmol), in DMF (15 mls) was added ethyl 6-bromohexanoate (1.30 g, 5.82 mmol) and potassium carbonate (1.23 g, 8.91 mmol). The mixture was stirred at 70 C. for 12 hours, cooled, poured into water and extracted twice with ethyl acetate. The combined organic fractions were washed once with water and dried over anhydrous magnesium sulfate. After the solvents were removed under reduced pressure, a red oil remained which was purified by column chromatography (70% hexane/30% ethyl acetate) to give 6-(5-formyl-2-nitro-phenoxy)-hexanoic acid ethyl ester as a yellow oil (1.00 g, 67%). 1H NMR (400 MHz, CDCl3) delta: 10.06 (s, 1H), 7.92 (d, 1H, J=8.8 Hz), 7.58 (d, 1H, J=1.2 Hz), 7.54 (dd, 1H, J=8 Hz, J=1.6 Hz), 4.20 (q, 2H, J=6.8 Hz), 4.14 (t, 2H, J=7.2 Hz), 2.36 (t, 2H, J=8.0 Hz), 1.90 (m, 2H), 1.73 (m, 2H), 1.57 (m, 2H), 1.29 (t, 3H, J=6.8 Hz). 13C NMR (400 MHz, CDCl3) delta: 173.79, 169.46, 151.87, 143.23, 133.66, 125.32, 121.93, 115.88, 69.65, 60.42, 34.12, 28.54, 25.40, 24.52, 14.25. IR (neat): 3396, 3110, 3080, 3047, 2944, 2869, 2735, 1730, 1705, 1607, 1531, 1489, 1465, 1434, 1381, 1351, 1311, 1272, 1161, 1093, 1063, 1030, 961, 863 cm-1.

Reference： [1]Patent: US2010/29952,2010,A1 .Location in patent: Page/Page column 17
[2]Journal of the American Chemical Society,2010,vol. 132,p. 15099 - 15101

42
[ 25542-62-5 ]
[ 693-04-9 ]
[ 110-38-3 ]

Reference： [1]Dalton Transactions,2013,vol. 42,p. 5150 - 5158
[2]Tetrahedron Letters,2009,vol. 50,p. 5644 - 5646

43
[ 25542-62-5 ]
[ 10111-08-7 ]
[ 1310071-57-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;	Example 1 Preparation of 1-(5-ethoxycarbonylpentyl)-imidazole-2-carboxaldehyde (Compound No. 31) A mixture of imidazole-2-carboxaldehyde (1 g), potassium carbonate (6 g) and 6-bromohexanoic acid ethyl ester (1.84 mL) was stirred at 70 C. for 12 hours. The mixture was cooled to room temperature and then partitioned between water (100 mL) and ether (150 mL). The ether layer was washed with water twice (2*100 mL) and saturated NaCl (150 mL), followed by drying over anhydrous Na2SO4. The solvent was removed by rotary evaporation to give the product, which was used in the subsequent synthesis without further purification.
	With potassium carbonate; at 70℃; for 12h;	A mixture of imidazole-2-carboxaldehyde (lg), potassium carbonate (6g) and 6-bromohexanoic acid ethyl ester (1.84 mL) was stirred at 70 C for 12 hours. The mixture was cooled to room temperature and then partitioned between water (100 mL) and ether (150 mL). The ether layer was washed with water twice (2x100 mL) and saturated NaCl (150 mL), followed by drying over anhydrous Na2S04. The solvent was removed by rotary evaporation to give the product, which was used in the subsequent synthesis without further purification.

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 9376 - 9392
[2]Patent: US2011/136201,2011,A1
[3]Patent: WO2011/68569,2011,A1 .Location in patent: Page/Page column 91-92

44
[ 25542-62-5 ]
[ 80441-55-0 ]

Reference： [1]Journal of the American Chemical Society,2011,vol. 133,p. 6587 - 6595

45
[ 957054-30-7 ]
[ 25542-62-5 ]
[ 1339922-65-4 ]
[ 1235450-11-9 ]

Yield	Reaction Conditions	Operation in experiment
34%; 20%	With potassium carbonate; In acetonitrile;Reflux;	Step 2a: Ethyl 6-(4-(6-((4-(methylsulfonyl)piperazin-l-yl)methyl)-4- morpholinothieno[3,2-d]pyrimidin-2-yl)-2H-indazol-2-yl)hexanoate (Compound 0116-4) and ethyl 3 -(4-(6-((4-(methylsulfonyl)piperazin- 1 -yl)methyl)-4- morpholinothieno [3 ,2- d]pyrimidin-2-yl)-l H-indazol- l-yl)propanoate (Compound 0115-4)A mixture of compound 0114 (160 mg, 0.31 mmol) , ethyl 6-bromohexanoate (83 mg, 0.37 mmol) and potassium carbonate (85 mg, 0.62 mmol) in acetonitrile (50 mL) was refluxed overnight. Solvent was removed and the residue was partitioned between dichloromethane and water. The organic layer was separated and washed with brine, dried over magnesium sulfate, filtered and evaporated in vacuo. The resulting residue was purified by prep-HPLC to give the title compound 0116-4 (40 mg, 20%) and 0115-4 (70 mg, 34%).Compound 0116-4: an oil; LCMS: 657 [M+l]+; 1H NMR (400 MHz, CDC13): delta 1.14 (t, J = 7.2 Hz, 3H), 1.34 (m, 2H), 1.60 (m, 2H), 2.02 (m, 2H), 2.22 (t, J= 7.2 Hz, 2H), 2.62 (s, 4H), 2.73 (s, 3H), 3.23 (m, 4H), 3.82 (s, 2H), 3.84 (m, 4H), 4.00 (m, 6H), 4.40 (t, J= 7.2 Hz, 2H), 7.33 (m, 2 H), 7.74 (d, J= 8.4 Hz, 1H), 8.19 (d, J= 6.8 Hz, 1H), 8.82 (s, 1H). 13C NMR (100 MHz, CDC13): delta 172.4, 161.7, 159.6, 156.7, 148.6, 147.5, 130.1, 124.6, 123.1, 122.1, 119.2, 118.8, 112.0, 65.8, 59.4, 56.4, 52.6, 51.2, 45.3, 44.8, 33.3, 32.9, 29.3, 25.1, 23.4, 13.4.Compound 0115-4: an oil; LCMS: 657 [M+l]+ ; 1H NMR (400 MHz, CDC13): deltaIota. Iota (t, J = 7.2 Hz, 3H), 1.27 (m, 2H), 1.59 (m, 2H), 1.90 (m, 2H), 2.19 (t, J = 7.2 Hz, 2H), 2.61 (m, 4H), 2.72 (s, 3H), 3.22 (m, 4H), 3.83 (m, 6H), 4.00 (m, 6H), 4.35 (t, J= 7.2 Hz, 2H), 7.31 (s, 1H), 7.41 (m, 2H), 8.16 (m, 1H), 8.81 (s, 1H).13C NMR (100 MHz, CDC13): delta 172.6, 161.7, 159.8, 157.1, 147.7, 139.2, 133.5, 131.2, 124.9, 123.2, 121.4, 120.7, 112.1, 109.7, 65.8 (2C), 59.2, 56.3, 51.4, 47.7, 45.6, 44.8, 33.5, 33.0, 28.6, 23.5, 19.8, 13.2.

Reference： [1]Patent: WO2011/130628,2011,A1 .Location in patent: Page/Page column 131-132

46
[ 25542-62-5 ]
[ 619-60-3 ]
ethyl 6-(4-(dimethylamino)phenoxy)hexanoate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2011,vol. 133,p. 16970 - 16976

47
[ 25542-62-5 ]
[ 57412-08-5 ]
5-[4-(5-carboxypentyloxy)phenyl]-10,15,20-tritolylporphyrin [ No CAS ]

Reference： [1]Monatshefte fur Chemie,2012,vol. 143,p. 153 - 159

48
[ 25542-62-5 ]
[ 57412-08-5 ]
5-[4-[5-(ethoxycarbonyl)pentyloxy]phenyl]-10,15,20-tritolylporphyrin [ No CAS ]

Reference： [1]Monatshefte fur Chemie,2012,vol. 143,p. 153 - 159

49
[ 25542-62-5 ]
[ 109555-87-5 ]
[ 1393345-74-8 ]

Yield	Reaction Conditions	Operation in experiment
86%		To a suspension of sodium hydride (1.1g, 30mmol, 60% in mineral oil) in DMF (100ml) under nitrogen was added solid 3-(1-naphthoyl)-1H-indole 1 (5.43g, 20mmol). After stirring at room temperature for 1h, a solution of <strong>[25542-62-5]ethyl 6-bromohexanoate</strong> (6.6g, 30mmol) in DMF (10ml) was added slowly with stirring over a period of 15 min and the mixture was then heated at 60C for 3h. The solvent was removed under high vacuum and the crude product was suspended in water (150ml) and extracted by ethyl acetate (2x150ml). The combined ethyl acetate phases were washed by water (1x100ml), brine (1x100ml), dried over sodium sulphate filtered and concentrated to dryness. The crude product obtained was purified by chromatography on silica gel using hexane/ethyl acetate (8/2) to give the title compound 2 as an oil which became solid in the cold (7.1g, 86%).
	With sodium hydride; In hexane; water; ethyl acetate; N,N-dimethyl-formamide; mineral oil;	Example-2 Preparation of N-(5-Ethoxycarbonylpentyl)-3-(1-naphthoyl)-1H-indole 2 To a suspension of sodium hydride (1.1 g, 30 mmol, 60% in mineral oil) in DMF (100 ml) under nitrogen was added solid 3-(1-naphthoyl)-1H-indole 1 (5.43 g, 20 mmol). After stirring at room temperature for 1 h, a solution of <strong>[25542-62-5]ethyl 6-bromohexanoate</strong> (6.6 g, 30 mmol) in DMF (10 ml) was added slowly with stirring over a period of 15 min and the mixture was then heated at 60 C. for 3 h. The solvent was removed under high vacuum and the crude product was suspended in water (150 ml) and extracted by ethyl acetate (2150 ml). The combined ethyl acetate phases were washed by water (1100 ml), brine (1*100 ml), dried over sodium sulphate filtered and concentrated to dryness. The crude product obtained was purified by chromatography on silica gel using hexane/ethyl acetate (8/2) to give the title compound 2 as an oil which became solid in the cold (7.1 g, 86%).

Reference： [1]Patent: EP2487155,2012,A1 .Location in patent: Page/Page column 8
[2]Patent: US2012/208213,2012,A1

50
[ 25542-62-5 ]
[ 1143-50-6 ]
[ 1396160-75-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 5360 - 5362

51
[ 25542-62-5 ]
[ 4877-80-9 ]
[ 1191091-67-4 ]

Reference： [1]Chemistry Letters,2009,vol. 38,p. 900 - 901,2

52
[ 25542-62-5 ]
1,2,3,9-tetrahydro-6-fluoro-2,2-dimethyl-4H-carbazol-4-one [ No CAS ]
[ 1432509-24-4 ]

Yield	Reaction Conditions	Operation in experiment
100%		Step 2. Synthesis of ethyl 6-(6-fluor-2,2-dimethyl-4-oxo-l ,2,3,4-tetrahydrocarbazol-9-yl) hexanoate [Foumula 1-3]6-fluoro-2,2-dimethyl-2,3-dihydro-lH-carbazol-4(9H)-on [formula 1-2] (0.1 g, 0.43 mmol) was dissolved in DMF (20 mL), and NaH(0.015 g, 0.645 mmol) was added and stirred for 10 minutes. Then, <strong>[25542-62-5]ethyl 6-bromohexanoate</strong> (0.096 g, 0.43 mmol) was added and stirred at 60C for 12 hours. After the completion of the reaction, DMF was distilled out under reduced pressure, the reaction mixture was extracted with ethyl acetate and saturated NaHC03 aqueous solution, the organic layer was washed with brine, dried over anhydrous Na2S04, filtered and concentrated under reduced pressure. Residue was purified by column chromatography (Si02; hexane/ethylacetate, 3/1 ) to yield the title compound (0.18 g, 100%).
100%		6-fluoro-2,2-dimethyl-2,3-dihydro-1H-carbazol-4(9H)-on [formula 1-2] (0.1 g, 0.43 mmol) was dissolved in DMF (20 mL), and NaH (0.015 g, 0.645 mmol) was added and stirred for 10 minutes. Then, <strong>[25542-62-5]ethyl 6-bromohexanoate</strong> (0.096 g, 0.43 mmol) was added and stirred at 60 C. for 12 hours. After the completion of the reaction, DMF was distilled out under reduced pressure, the reaction mixture was extracted with ethyl acetate and saturated NaHCO3 aqueous solution, the organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. Residue was purified by column chromatography (SiO2; hexane/ethylacetate, 3/1) to yield the title compound (0.18 g, 100%).

Reference： [1]Patent: WO2013/62344,2013,A1 .Location in patent: Page/Page column 50
[2]Patent: US2014/315889,2014,A1 .Location in patent: Paragraph 0252-0254

53
[ 40429-04-7 ]
[ 25542-62-5 ]
[ 1432509-05-1 ]

Yield	Reaction Conditions	Operation in experiment
64%	With sodium hydride; In N,N-dimethyl-formamide; at 60℃; for 6h;	Step 2. Synthesis of ethyl 6-(2,2-dimethyl-4-oxo-l,2,3,4-tetrahydrocarbazol-9-yl)hexanoate [formula 1-3] 2,2-dimethyl-2,3-dihydro-lH-carbazol-4(9H)-on [formula 1-2] (0.1 g, 0.46 mmol) was dissolved in DMF (10 mL), then ethyl 6-bromohexanoate (0.1 g, 0.46 mmol), and NaH (0.014 g, 0.59 mmol) were added and stirred at 60C for 6 hours. After the completion of the reaction, DMF was distilled out under reduced pressure, the reaction mixture was extracted with ethyl acetate and saturated NaHC03 aqueous solution, the the organic layer was washed with brine, dried over anhydrous Na2S04, filtered and concentrated under reduced pressure. Residue was purified by column chromatography (Si02; hexane/ethylacetate, 4/1) to yield the title compound (0.104 g, 64%).
64%	With sodium hydride; In N,N-dimethyl-formamide; at 60℃; for 6h;	(0.1 g, 0.46 mmol) was dissolved in DMF (10 mL), then ethyl 6-bromohexanoate (0.1 g, 0.46 mmol), and NaH (0.014 g, 0.59 mmol) were added and stirred at 60 C. for 6 hours. After the completion of the reaction, DMF was distilled out under reduced pressure, the reaction mixture was extracted with ethyl acetate and saturated NaHCO3 aqueous solution, the organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. Residue was purified by column chromatography (SiO2; hexane/ethylacetate, 4/1) to yield the title compound (0.104 g, 64%).

Reference： [1]Patent: WO2013/62344,2013,A1 .Location in patent: Page/Page column 30
[2]Patent: US2014/315889,2014,A1 .Location in patent: Paragraph 0162-0164

54
[ 15128-52-6 ]
[ 25542-62-5 ]
[ 1432509-77-7 ]

Yield	Reaction Conditions	Operation in experiment
35%		1. Synthesis of ethyl 6-(4-oxo-l,2,3,4-tetrahydrocarbazol-9-yl)hexanoate[formula 1-3]2,3-dihydro-lH-carbazol-4(9H)-on) [formula 2-2] (1.0 g, 5.40 mmol) was dissolved in D F (20 mL), 55% NaH in paraffin solution (0.471 g, 10.8 mmol) was added and stirred for 10 minutes. Then, ethyl 6-bromomhexanoate (1.45 g, 6.48 mmol) was added and stirred at 50C for 5 hours. After the completion of the reaction, DMF was distilled out, the reaction mixture was extracted with ethyl acetate and saturated NaHC03 aqueous solution, and the organic layer was washed with brine, dried over anhydrous Na2S04, filtered and concentrated under reduced pressure. Residue was purified by column chromatography (Si02; hexane/ethylacetate, 6/1) to yield the title compound (0.61 g, 35 %).
35%		2,3-dihydro-1H-carbazol-4(9H)-on) [formula 2-2] (1.0 g, 5.40 mmol) was dissolved in DMF (20 mL), 55% NaH in paraffin solution (0.471 g, 10.8 mmol) was added and stirred for 10 minutes. Then, ethyl 6-bromomhexanoate (1.45 g, 6.48 mmol) was added and stirred at 50 C. for 5 hours. After the completion of the reaction, DMF was distilled out, the reaction mixture was extracted with ethyl acetate and saturated NaHCO3 aqueous solution, and the organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. Residue was purified by column chromatography (SiO2; hexane/ethylacetate, 6/1) to yield the title compound (0.61 g, 35%).

Reference： [1]Patent: WO2013/62344,2013,A1 .Location in patent: Page/Page column 107
[2]Patent: US2014/315889,2014,A1 .Location in patent: Paragraph 0506-0508

55
[ 957054-30-7 ]
[ 25542-62-5 ]
[ 1235450-11-9 ]
[ 1235450-12-0 ]

Yield	Reaction Conditions	Operation in experiment
20%; 34%	With potassium carbonate; In acetonitrile;Reflux;	Step 2a: Ethyl 6-(4-(6-(4-(methylsulfonyl)piperazin-1-yl)methyl)-4-morpholinothieno[3,2-d]pyrimidin-2-yl)-2H-indazol-2-yl)hexanoate (Compound 0116-4) and ethyl 3-(4-(6-((4-(methylsulfonyl)piperazin-1-yl)methyl)-4-morpholinothieno[3,2-d]pyrimidin-2-yl)-1H-indazol-1-yl)propanoate (Compound 0115-4)[0185]A mixture of compound 0114 (160 mg, 0.31 mmol), ethyl 6-bromohexanoate (83 mg, 0.37 mmol) and potassium carbonate (85 mg, 0.62 mmol) in acetonitrile (50 mL) was refluxed overnight. Solvent was removed and the residue was partitioned between dichloromethane and water. The organic layer was separated and washed with brine, dried over magnesium sulfate, filtered and evaporated in vacuo. The resulting residue was purified by prep-HPLC to give the title compound 0116-4 (40 mg, 20%) and 0115-4 (70 mg, 34%).[0186]Compound 0116-4: an oil; LCMS: 657 [M+1]+; 1H NMR (400 MHz, CDCl3): delta 1.14 (t, J=7.2 Hz, 3H), 1.34 (m, 2H), 1.60 (m, 2H), 2.02 (m, 2H), 2.22 (t, J=7.2 Hz, 2H), 2.62 (s, 4H), 2.73 (s, 3H), 3.23 (m, 4H), 3.82 (s, 2H), 3.84 (m, 4H), 4.00 (m, 6H), 4.40 (t, J=7.2 Hz, 2H), 7.33 (m, 2H), 7.74 (d, J=8.4 Hz, 1H), 8.19 (d, J=6.8 Hz, 1H), 8.82 (s, 1H). 13C NMR (100 MHz, CDCl3): delta 172.4, 161.7, 159.6, 156.7, 148.6, 147.5, 130.1, 124.6, 123.1, 122.1, 119.2, 118.8, 112.0, 65.8, 59.4, 56.4, 52.6, 51.2, 45.3, 44.8, 33.3, 32.9, 29.3, 25.1, 23.4, 13.4.[0187]Compound 0115-4: an oil; LCMS: 657 [M+1]+; 1H NMR (400 MHz, CDCl3): delta1.14 (t, J=7.2 Hz, 3H), 1.27 (m, 2H), 1.59 (m, 2H), 1.90 (m, 2H), 2.19 (t, J=7.2 Hz, 2H), 2.61 (m, 4H), 2.72 (s, 3H), 3.22 (m, 4H), 3.83 (m, 6H), 4.00 (m, 6H), 4.35 (t, J=7.2 Hz, 2H), 7.31 (s, 1H), 7.41 (m, 2H), 8.16 (m, 1H), 8.81 (s, 1H). 13C NMR (100 MHz, CDCl3): delta 172.6, 161.7, 159.8, 157.1, 147.7, 139.2, 133.5, 131.2, 124.9, 123.2, 121.4, 120.7, 112.1, 109.7, 65.8 (2C), 59.2, 56.3, 51.4, 47.7, 45.6, 44.8, 33.5, 33.0, 28.6, 23.5, 19.8, 13.2.
20%; 34%	With potassium carbonate; In acetonitrile;Reflux;	In acetonitrile (50 mL), Compound 0114 (160mg, 0.31mmol), ethyl 6-bromo-hexanoate (83mg, 0.37mmol) and potassium carbonate (85mg, 0.62mmol) and the mixture was refluxed overnight. The solvent was removed, the residue was partitioned between dichloromethane and water. The organic layer was separated, washed with brine, dried over magnesium sulfate, filtered and evaporated in vacuo. The resulting residue was purified by preparative HPLC to give the title compound 0116-4 (40mg, 20%) and 0115-4 (70mg, 34%).

Reference： [1]Patent: US2013/102595,2013,A1 .Location in patent: Paragraph 0184-0187
[2]Patent: JP2015/187145,2015,A .Location in patent: Paragraph 0181

56
[ 25542-62-5 ]
[ 677-22-5 ]
ethyl 7,7-dimethyloctanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With cobalt(II) chloride; lithium iodide; isoprene; In tetrahydrofuran; at -78 - 50℃; for 5h;Inert atmosphere;	General procedure: Coupling of Alkyl Halides with t-BuMgCl; Procedure 1 (P1)An alkyl halide (1.0 mmol), decane (63 mg as an internal standard)and LiI (5.3 mg, 0.04 mmol) were added to a dry, nitrogen-flushedtest tube equipped with a rubber septum and a magnetic stir bar.THF (0.8 mL) was added and the solution was cooled to -78 C usinga dry ice/EtOH bath. t-BuMgCl (2a) (1.5 mL, 0.81 M in THF,1.2 mmol) was added slowly followed by isoprene (136.2 mg, 2.0mmol). To this mixture was added CoCl2 [2.6 mg, 0.02 mmol, as apowder or as a THF solution (0.5 mL, 0.04 M)]. (Note 1: CoCl2should be added after isoprene, otherwise the catalytic performancedecreases significantly). The cold bath was removed and the mixturewas warmed to r.t. (ca. over 10 min), and then heated for 5 h bysuspending the reaction vessel in an oil bath kept at 50 C. (Note 2:when the reaction mixture was heated at 30 C during this stage, unidentifiedside reactions occurred resulting in low yields of couplingproducts). The resulting mixture was cooled to 0 C in an ice bathand the reaction was quenched with aq HCl (5 mL, 1 M). The productwas extracted with Et2O (3 × 20 mL). The combined organiclayer dried over Na2SO4, concentrated and analyzed by gas chromatographyto determine the GC yield. The residue was purified by silicagel column chromatography or by GPC. According to P1, <strong>[25542-62-5]ethyl 6-bromohexanoate</strong> (4m) (223 mg, 1.0 mmol)and t-BuMgCl (2a) (0.81 M in THF, 1.2 mmol) were reacted understandard conditions. After aqueous work-up, purification by flashcolumn chromatography (hexane-EtOAc, 10:1) afforded the titlecompound.Yield: 145 mg (72%); colorless oil.IR (Zn/Se-ATR, neat): 2952, 2865, 1739, 1468, 1382, 1365, 1241,1182, 1127, 1084, 1036, 935 cm-1.1H NMR (400 MHz, CDCl3): delta = 0.86 (s, 9 H), 1.13-1.17 (m, 2 H),1.23-1.28 (m, 7 H), 1.63 (quin, J = 7.3 Hz, 2 H), 2.29 (t, J = 7.3 Hz,2 H), 4.12 (q, J = 6.9 Hz, 2 H).13C NMR (100 MHz, CDCl3): delta = 14.2, 24.2, 25.0, 29.4, 30.1, 30.2,34.4, 44.0, 60.1, 174.0.MS (EI): m/z (%) = 200 (21) [M]+, 185 (14), 171 (11), 170 (7), 155(4), 143 (51), 114 (3).HRMS (EI): m/z [M]+ calcd for C12H24O2: 200.1776; found:200.1773.

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 9604 - 9607
[2]Synthesis,2014,vol. 46,p. 1583 - 1592

57
[ 25542-62-5 ]
[ 201230-82-2 ]
[ 623-49-4 ]
C₁₃H₂₁NO₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; at 80℃; under 60804.1 Torr; for 3h;	General procedure: Typical procedure for radical/ionic three-component coupling reaction leading to cyanohydrin derivatives 1-cyanononyl ethyl carbonate (3a) [34] (Table 1, entry 1): A mixture of 1-bromooctane (1a, 96.6 mg, 0.5 mmol), ethyl cyanoformate (2a, 79.3 mg, 0.8 mmol), tributyltin hydride (174.6 mg, 0.6 mmol), triethylamine (13.2 mg, 0.13 mmol), and AIBN (24.6 mg, 0.15 mmol) in C6H6 (17 mL) were placed in a 100 mL stainless steel autoclave. The reaction mixture was degassed 3 times with 10 atm of CO and charged with 90 atm of CO at -40 C (MeCN-dry ice bath). Then the autoclave was allowed to warm to room temperature, which caused the pressure gauge to indicate 120 atm. Then the reaction was conducted at 80 C for 3 h. After cooling to room temperature, the reaction mixture was concentrated and purified by silica gel flash chromatography (hexane/EtOAc 97:3) to afford 3a (95.3 mg, 79%).

Reference： [1]Beilstein Journal of Organic Chemistry,2014,vol. 10,p. 150 - 154

58
[ 25542-62-5 ]
[ 79722-21-7 ]
[ 1628321-41-4 ]

Yield	Reaction Conditions	Operation in experiment
86%		General procedure: EXAMPLE 1 [0067] This example demonstrates the synthesis of N-alkylated-JV-Boc-O- benzylhydroxylamines la-c (Figure 1) in an embodiment of the invention. [0068] N-Boc-O-benzylhydroxylamine (5.00 g, 22.4 mmol) under nitrogen atmosphere was dissolved in dry DMF (100 mL) and cooled in an ice bath. 60% sodium hydride (887 mg, 22.2 mmol) was added and the mixture was stirred until end of hydrogen evolution (~ 30 min). Ethyl-6-bromohexanoate (6.19 g, 28 mmol) was added and the mixture was heated for 14 h at 65 C. The DMF was then evaporated in vacuo, the residue was dissolved in AcOEt and washed twice with water. After drying the organic layer with MgS04, the oil obtained after filtration and concentration was purified by flash chromatography using hexane/acetone (9/1), affording la as a colorless oil (7.04 g, 86%). 1H NMR (CDC13, 300 MHz, ppm): delta 1.24 (t, 3H, J= 7.2 Hz), 1.31 (m, 2H), 1.50 (s, 9H), 1.61 (m, 4H), 2.28 (t, 2H, J= 7.5 Hz), 3.40 (t, 2H, J= 12 Hz), 4.1 1 (q, 2H, J= 7.2 Hz), 4.82 (s, 2H), 7.36 (m, 5H). I3C NMR (CDC13, 75 MHz, ppm): delta 14.4, 24.8, 26.5, 26.9, 28.5, 34.4, 49.6, 60.4, 77.1, 81.4, 128.6(2), 129.5, 135.9, 156.8, 173.8. ESI-MS: m/z = 266.2 [M+H]+. [0069] The same alkylation procedure using ethyl-7-bromoheptanoate provided lb as a colorless oil (91%). 1H NMR (CDC13, 300 MHz, ppm): delta 1.24 (t, 3H, J= 7.2), 1.31 (m, 4H), 1.50 (s, 9H), 1.60 (m, 4H), 2.27 (t, 2H, J= 7,5 Hz), 3.40 (t, 2H, J= 6.9 Hz), 4,1 1 (q, 2H, J = 6.9 H), 4.82 (s, 2H), 7.33 (m, 5H). I3C NMR (CDC13, 75 MHz, ppm): delta 14.3, 24.9, 26.5, 26.9, 28.4, 28.8, 34.3, 49.6, 60.2, 76.9, 81.1, 128.4, 128.5, 129.4, 135.8, 156.6, 173.7. ESI- MS: m/z = 402.2 [M+Na]+.
		A solution of tert-butyl-N-(benzyloxy)carbamate (4.00 g, 17.9 mmol) in DMF (20 mL) wasadded slowly to a suspension of sodium hydride (60% in mineral oil) (0.932 g; 23.3 mmol) inDMF (52 mL) at 0C. The reaction was stirred at 0C for 1 h, then ethyl 6-bromohexanoate (15.9 mL, 89.6 mmol) was added. The reaction mixture was stirred at room temperature for 1 hour. The reaction was quenched with sat. ammonium chloride solution (130 ml) and the mixture was extracted with DCM (3x 200 ml). The combined organic layers were dried(Na2SO4), filtered and concentrated in vacuo. The obtained crude material (la) was used in the next step without further purification.

Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 5584 - 5591
[2]Patent: WO2014/164988,2014,A1 .Location in patent: Paragraph 0067-0068; sheet 1
[3]Patent: WO2018/11266,2018,A1 .Location in patent: Page/Page column 82

59
[ 19315-93-6 ]
[ 25542-62-5 ]
[ 1616589-81-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 3720 - 3731

60
[ 6093-68-1 ]
[ 25542-62-5 ]
[ 1616590-28-3 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 6-hydroxycoumarin With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.566667h; Stage #2: 6-bromo-hexanoic acid ethyl ester In N,N-dimethyl-formamide; mineral oil at 0 - 110℃;	5.1.1 6-(3,4-Dihydrocarbostyril-6-yloxy)hexanoic acid ethyl ester (representative of compound 45) as the general procedure for the synthesis of the intermediate of 1-11 General procedure: A solution of 6-hydroxy-3,4-dihydrocarbostyril (corresponding to 44) (2.00g, 12.26mmol) in DMF (10ml) was added dropwise to a suspension of NaH (60% in mineral oil, 0.59g, 14.71mmol) in DMF (5ml) for 14min at 0°C with a CaCl2 tube. After stirring for 20min at 0°C, a solution of 6-bromohexanoic acid ethyl ester (3.06g, 13.48mmol) in DMF (7ml) was added dropwise to the reaction mixture for 7min at 0°C. The reaction mixture was stirred overnight, during which time the ice was allowed to gradually melt and was subsequently stirred for 3h at 110°C. After cooling, H2O (100ml) was added to the mixture, and the resulting mixture was extracted with AcOEt (100ml×3). The combined organic layer was washed with H2O (100ml×1) and brine (100ml×1), dried over Na2SO4 (anhyd), filtered, and concentrated under reduced pressure. The crude product was purified through open silica gel column chromatography (n-hexane/AcOEt=1:2) to afford a colorless solid (2.56g, 8.38mmol, y. 68%).

Reference： [1]Tashima, Toshihiko; Murata, Hiroaki; Kodama, Hidehiko [Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 14, p. 3720 - 3731]

61
[ 25542-62-5 ]
[ 70500-72-0 ]
[ 62969-74-8 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: A solution of 6-hydroxy-3,4-dihydrocarbostyril (corresponding to 44) (2.00g, 12.26mmol) in DMF (10ml) was added dropwise to a suspension of NaH (60% in mineral oil, 0.59g, 14.71mmol) in DMF (5ml) for 14min at 0C with a CaCl2 tube. After stirring for 20min at 0C, a solution of 6-bromohexanoic acid ethyl ester (3.06g, 13.48mmol) in DMF (7ml) was added dropwise to the reaction mixture for 7min at 0C. The reaction mixture was stirred overnight, during which time the ice was allowed to gradually melt and was subsequently stirred for 3h at 110C. After cooling, H2O (100ml) was added to the mixture, and the resulting mixture was extracted with AcOEt (100ml×3). The combined organic layer was washed with H2O (100ml×1) and brine (100ml×1), dried over Na2SO4 (anhyd), filtered, and concentrated under reduced pressure. The crude product was purified through open silica gel column chromatography (n-hexane/AcOEt=1:2) to afford a colorless solid (2.56g, 8.38mmol, y. 68%).

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 3720 - 3731

62
[ 30389-33-4 ]
[ 25542-62-5 ]
[ 1616590-30-7 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: A solution of 6-hydroxy-3,4-dihydrocarbostyril (corresponding to 44) (2.00g, 12.26mmol) in DMF (10ml) was added dropwise to a suspension of NaH (60% in mineral oil, 0.59g, 14.71mmol) in DMF (5ml) for 14min at 0C with a CaCl2 tube. After stirring for 20min at 0C, a solution of 6-bromohexanoic acid ethyl ester (3.06g, 13.48mmol) in DMF (7ml) was added dropwise to the reaction mixture for 7min at 0C. The reaction mixture was stirred overnight, during which time the ice was allowed to gradually melt and was subsequently stirred for 3h at 110C. After cooling, H2O (100ml) was added to the mixture, and the resulting mixture was extracted with AcOEt (100ml×3). The combined organic layer was washed with H2O (100ml×1) and brine (100ml×1), dried over Na2SO4 (anhyd), filtered, and concentrated under reduced pressure. The crude product was purified through open silica gel column chromatography (n-hexane/AcOEt=1:2) to afford a colorless solid (2.56g, 8.38mmol, y. 68%).

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 3720 - 3731

63
[ 30389-33-4 ]
[ 25542-62-5 ]
[ 1616589-91-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 3720 - 3731

64
[ 54197-66-9 ]
[ 25542-62-5 ]
[ 1616590-26-1 ]

Yield	Reaction Conditions	Operation in experiment
68%		General procedure: A solution of 6-hydroxy-3,4-dihydrocarbostyril (corresponding to 44) (2.00g, 12.26mmol) in DMF (10ml) was added dropwise to a suspension of NaH (60% in mineral oil, 0.59g, 14.71mmol) in DMF (5ml) for 14min at 0C with a CaCl2 tube. After stirring for 20min at 0C, a solution of 6-bromohexanoic acid ethyl ester (3.06g, 13.48mmol) in DMF (7ml) was added dropwise to the reaction mixture for 7min at 0C. The reaction mixture was stirred overnight, during which time the ice was allowed to gradually melt and was subsequently stirred for 3h at 110C. After cooling, H2O (100ml) was added to the mixture, and the resulting mixture was extracted with AcOEt (100ml×3). The combined organic layer was washed with H2O (100ml×1) and brine (100ml×1), dried over Na2SO4 (anhyd), filtered, and concentrated under reduced pressure. The crude product was purified through open silica gel column chromatography (n-hexane/AcOEt=1:2) to afford a colorless solid (2.56g, 8.38mmol, y. 68%). Colorless needles (n-hexane/AcOEt). Mp 79-80C. 1H NMR (300MHz/CDCl3) delta 1.26 (3H, t, J=7.2Hz, CH2CH3), 1.47-1.52 (2H, m, CH2), 1.65-1.81 (4H, m, CH2×2), 2.33 (2H, t, J=7.4Hz, CH2), 2.61 (2H, t, J=7.5Hz, CH2), 2.93 (2H, t, J=7.4Hz, CH2), 3.92 (2H, t, J=6.5Hz, CH2), 4.13 (2H, q, J=7.2Hz, CH2CH3), 6.65-6.69 (2H, m, ArH), 6.72 (1H, s, ArH), 7.91 (1H, s, NH).

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 3720 - 3731

65
[ 36404-89-4 ]
[ 25542-62-5 ]
ethyl 6-((3-formylpyridin-2-yl)oxy)hexanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
9.2%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 4h;Inert atmosphere;	In a 50-mL round bottom flask, a stirred solution of <strong>[36404-89-4]2-hydroxynicotinaldehyde</strong> (1.5 g, 12.19 mmol) in DMF (30 mL), was treated with potassium carbonate (5.0 g, 36.58 mmol) and ethyl 6-bromohexanoate (2.99 g, 13.41 mmol) at rt under nitrogen atmosphere. The reaction mixture was stirred at rt for 4 h. Upon completion of the reaction (TLC), the reaction mixture was diluted with cold water and extracted with ethyl acetate (50 mL x 2). The combined organic extract was washed with brine, dried over anhydrous NaiSCu and concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography (elution 10% EtOAc-hexanes) to give title compound (0.297 g, 9.2%) as the clear oil. NMR (300 MHz, CDCL): delta 10.38 (s, 1H), 8.36 - 8.34 (m, lH), 8.09 (dd, J =7.5, 2.1 Hz, 1H), 7.00 - 6.96 (m, 1H), 4.44 (t, J= 13.2, 6.6 Hz, 2H), 4.17 - 4.08 (m, 2H), 2.35 (t, J= 13.2, 7.2 Hz, 2H), 1.90 - 1.85 (m, 2H ) 1.77 - 1.65 (m, 2H), 1.56 -1.46 (m, 2H), 1.24 (t, J = 7.2 Hz, 3H). LCMS (m/z): Desired mass peak not observed.
9.2%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 4h;Inert atmosphere;	In a 50-mt round bottom flask, a stirred solution of <strong>[36404-89-4]2-hydroxynicotinaldehyde</strong> (1.5 g, 12.19 mmol) in DMF (30 mL), was treated with potassium carbonate (5.0 g, 36.58 mmol) and ethyl 6-bromohexanoate (2.99 g, 13.41 mmol) at rt under nitrogen atmosphere. The reaction mixture was stirred at rt for 4 h. Upon completion of the reaction (TLC), the reaction mixture was diluted with cold water and extracted with ethyl acetate (50 mL x 2). The combined organic extract was washed with brine, dried over anhydrous Na2SO4and concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography (elution 10% EtOAc-hexanes) to give title compound (0.297 g, 9.2%) as the clear oil. ?H NMR (300 MHz, CDC13): 10.38 (s, 1H), 8.36 - 8.34 (m,1H), 8.09 (dd, J =7.5, 2.1 Hz, 1H), 7.00 - 6.96 (m, 1H), 4.44 (t, J= 13.2, 6.6 Hz, 2H), 4.17-4.08 (m, 2H), 2.35 (t, J= 13.2, 7.2 Hz, 2H), 1.90- 1.85 (m, 2H)1.77- 1.65 (m, 2H), 1.56 -1.46 (m, 2H), 1.24 (t, J= 7.2 Hz, 3H). LCMS (m/z): Desired mass peak notobserved.

Reference： [1]Patent: WO2014/165827,2014,A1 .Location in patent: Page/Page column 126
[2]Patent: WO2016/57322,2016,A1 .Location in patent: Page/Page column 160

66
[ 25542-62-5 ]
[ 1761-61-1 ]
ethyl 6-(4-bromo-2-formylphenoxy)hexanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With potassium carbonate; In N,N-dimethyl-formamide; at 20 - 90℃; for 4h;Inert atmosphere;	In a 50-mL round bottom flask, a stirred solution of substituted 5-bromo-2-hydroxybenzaldehyde (5.0 g, 24.8 mmol) in DMF (30 mL), was treated with potassium carbonate (10.26g, 74.4 mmol) and ethyl 6- bromohexanoate (6.6g, 29.8 mmol) at rt under nitrogen atmosphere. The reaction mixture was heated at 90C for 4 h. Upon completion of the reaction (TLC) the reaction mixture was cooled to rt, diluted with cold water and extracted ethyl acetate (250 mL x 2). The combined organic extract was washed with brine and dried over anhydrous NaiSO t. The solution was concentrated under reduced pressure to give the title compound (7.97 g, 94%) as yellow oil. LCMS (m/z): 343.2 (M+l)+.
94%	With potassium carbonate; In N,N-dimethyl-formamide; at 90℃; for 4h;Inert atmosphere;	In a 50-mL round bottom flask, a stuffed solution of substituted 5-bromo-2-hydroxybenzaldehyde(5.0 g, 24.8 mmol) in DMF (30 mL), was treated with potassium carbonate (10.26g, 74.4 mmol) and <strong>[25542-62-5]ethyl 6-bromohexanoate</strong> (6.6g, 29.8 mmol) at rt under nitrogen atmosphere. The reaction mixture was heated at 90C for 4 h. Upon completion of the reaction (TLC) the reaction mixture was cooled to rt, diluted with cold water and extracted ethyl acetate (250 mL x 2). The combined organic extract was washed with brine and dried over anhydrous Na2SO4. The solution was concentrated under reduced pressure to give the titlecompound (7.97 g, 94%) as yellow oil. LCMS (m/z): 343.2 (M+1).

Reference： [1]Patent: WO2014/165827,2014,A1 .Location in patent: Page/Page column 131
[2]Patent: WO2016/57322,2016,A1 .Location in patent: Page/Page column 165

67
[ 25542-62-5 ]
[ 520-36-5 ]
C₂₃H₂₄O₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 8h; Inert atmosphere;	3.1 Synthesis of compound 2a General procedure: Ethylbromoacetate (1 equiv) was added dropwise to a solution of apigenin(1 equiv) with anhydrous K2CO3(1 equiv) in anhydrous N,N-Dimethylformamide in ice bath under an atmosphere of argon, and stirring was continued for 8 h at room temperature. The product was purified by silica gel chromatography (normal phase, 15-25% ethyl acetate in hexanes gradient). Compounds 2b-f were synthesized according to the method for 2a.

Reference： [1]Su, Zhuo-Ran; Fan, Shi-Yong; Shi, Wei-Guo; Zhong, Bo-Hua [Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 14, p. 2778 - 2781]

68
[ 6478-79-1 ]
[ 25542-62-5 ]
C₁₆H₂₀Cl₂N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.75 g		To sodium hydride (300 mg) in DMF at 0 C. was added 5,6-dichloro-2-methylbenzoimidazole (500 mg) in one portion. The mixture was stirred at 0 C. for 15 minutes, followed by addition of ethyl 6-bromohexanoate (0.66 mL). The mixture was stirred at 0 C. for another 15 minutes and then at room temperature for 1 hour. The solution was concentrated to dryness under vacuum and the residue was purified by column chromatography on silica gel to give pale brown solid (0.75 g).

Reference： [1]Patent: US9097667,2015,B2 .Location in patent: Page/Page column 172

69
[ 6478-79-1 ]
[ 25542-62-5 ]
C₂₂H₃₁Cl₂N₂O₄⁽¹⁺⁾*Br^(1-) [ No CAS ]

Reference： [1]Patent: US9097667,2015,B2

70
[ 25542-62-5 ]
[ 114744-51-3 ]
ethyl 6-(7-bromo-3,4-dihydroquinolin-1(2H)-yl)hexanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 18.0h;	7-bromo-l, 2,3,4-tetrahydroquinoline (5. 0 g, 23.6 mmol) was dissolved in DMF (10 mL). Potassium carbonate (6.4 g) and 6-bromohexanoate ethyl ester (10.0 g, 47.2 mmol) were added into the solution. The mixture was heated to 100 C for 18 hours. After the reaction was cooled down, 50 niL of dichloromethane was added and washed with 10 niL of water three times. The organic layer was dried over sodium sulfate and concentrated. It was purified by flash chromatography in silica gel with hexanes-ethyl acetate to afford ethyl 6-(7-bromo-3,4- dihydroquinolin-l(2H)-yl)hexanoates as a clear oil (yield : 70%). H NMR (CDC13): delta 6.79 (d, 1H), 6.64 (d, 2H), 4.15 (t, 2H), 3.29 (t, 2H), 3.21 (t, 2H), 2.32 (t, 2H), 1.92 (m, 2H), 1.72 (m, 2H), 1.65 (m, 2H), 1.43 (m, 2H), 1.31 (t, 3H).

Reference： [1]Patent: WO2015/175870,2015,A1 .Location in patent: Page/Page column 103-104

71
[ 10576-12-2 ]
[ 25542-62-5 ]
ethyl 6-(((1-ethoxyethylidene)amino)oxy)hexanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 20℃; for 18h;	In a 500 mL flask were combined ethyl N-hydroxyacetimidate (6.1 8 g, 59.9 mmol), ethyl 6-bromohexanoate (8.9 mL, 50 mmol) and N,N-dimethylformamide (DMF, 1 00 mL). NaH (60% in mineral oil, 2.20 g, 55 mmol) was added to the flask in several portions with stirring at 20oC and the reaction was stirred at 20 oC for 18 h. The reaction mixture was poured into 200 mL of saturated aq NH4Cl with 150mL ice, and stirred until ice melted. The mixture was extracted with EtOAc (125 mLx3). The combined organic layers was successively washed with 100mL each of 10% aq citric acid, water, saturated aq NaHCO3, and saturated aq NaCl, dryed over MgSO4, filtered and concentrated, affording 12.6 g of reddish oil as crude product. The crude oil was distilled using a Buechi glass oven at less than 1 mbar. Ethyl 6-(((1 -ethoxyethylidene)amino)oxy)hexanoate was obtained as a colorless oil. MS (ESI+) calc 246.2, found 246.1 (M+1 ). 1H NMR (400 MHz, CDCl3): 4.1 21 (q, 2H, J=4.7Hz), 4.004 (q, 2H, J=4.7Hz), 3.881 (t, 2H, J=4.4Hz), 2.303 (t, 2H, J=5.0Hz), 1.920 (s, 3H), 1.686-1 .616 (m, 4H), 1.41 8-1.366 (m, 2H), 1.266 (t, 3H, J=4.8Hz), 1.249 (t, 3H, J=4.8Hz). Ethyl 6-(((1 -ethoxyethylidene)amino)oxy)hexanoate (2.457 g, 10.0 mmol) was charged in a 100mL round bottom flask, and dissolved in THF (30mL). Aqeous LiOH (1 .0 M, 10.0 mL) was added to the reaction, and the reaciton was stirred at 20 oC for 16 h. An additonal 2.5mL of 1 M aq LiOH was added to the reaction and the reaction was stirred at 50oC for 13 h. LCMS anlysis indicated completion of the reaction. THF was removed by evaporation, and the remaining mixture was lyophilized, affording Lithium (E)-6-(((1 -ethoxyethylidene)amino)oxy)hexanoate (I-1) as a white solid. MS (ESI+) calc 21 8.1 , found 218.1 (M+1 , H form). 1H NMR (400 MHz, MeOH-d4): 3.980 (q, 2H, J=7.2Hz), 3.861 (t, 2H, J=6.6Hz), 2.161 (t, 2H, J= 7.6Hz), 1 .883 (s, 3H), 1.665- 1.588 (m, 4H), 1 .431 -1.370 (m, 2H), 1.250 (t, 3H, J= 7.0Hz). 13C NMR (1 00 MHz, MeOH- d4): 1 82.976, 1 63.331 , 74.495, 63.180, 39.324, 29.972, 27.737, 27.394, 14.779, 1 3.646.

Reference： [1]Patent: WO2015/189791,2015,A1 .Location in patent: Page/Page column 76; 77

72
[ 25542-62-5 ]
4-(3-furyl)-2-(piperazin-1-yl)pyrimidine [ No CAS ]
ethyl 3-{4-[4-(3-furyl)pyrimidin-2-yl]piperazin-1-yl}}hexanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium carbonate; In acetonitrile; at -10 - 23℃; for 2h;	General procedure: In the preparation of compounds 3-10, a mixture of 4-(3-furyl)-2-(piperazin-1-yl)pyrimidine(1, 200 mg, 0.87 mmol), synthesized as described above, and anhydrous potassium carbonate (300 mg,2.2 mmol) in anhydrous acetonitrile (10 mL) was stirred at 10 C and treated with ethyl bromide,propyl bromide, benzyl chloride, benzoyl chloride, 3-phenylpropyl bromide, 2-bromoethanol, ethyl3-bromopropionate or <strong>[25542-62-5]ethyl 6-bromohexanoate</strong> (2.0 mmol) (Scheme 2). The mixture was stirred at 23 Cfor 2 h and then quenched with water (2 mL) and extracted with ether (3 x 20 mL). The extract was dried with anhydrous sodium sulfate and concentrated. Purification by chromatography eluting withdichloromethane/methanol (10:1) gave product 3-10.

Reference： [1]Molecules,2016,vol. 21

73
[ 25542-62-5 ]
2-((2-(4-bromophenyl)-5-methyl-1H-imidazol-1-yl)methyl)phenol [ No CAS ]
ethyl 6-(2-((2-(4-bromophenyl)-5-methyl-1H-imidazol-1-yl) methyl)phenoxy)hexanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97.2%	With potassium carbonate; In N,N-dimethyl-formamide; at 65℃; for 4h;Inert atmosphere;	In a 250 mL round bottom flask, a stirred solution of 2-((2-(4-bromophenyl)-5- methyl- 1H-imidazol- 1-yl)methyl)phenol (0.15 g, 0.44 mmol) in DMF (5 mL) was treated with K2C03 (0.18 g, 1.31 mmol) and <strong>[25542-62-5]ethyl 6-bromohexanoate</strong> (0.117 g, 0.52 mmol) at RT under nitrogen atmosphere. The resulting reaction mixture was stirred at 65 C for 4 h. Upon completion of the reaction (TLC), the reaction mixture was cooled to RT, solid was filtered and washed with EtOAc. The combined filtrate was concentrated under reduced pressure and the residue obtained was diluted with cold water (50 mL), before extracting with EtOAc (200 mL). The organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography (gradient elution, 15-30% EtOAc in hexanes). Yield: 0.205 g (97.2%). LCMS (ESI+, m/z): 485.1, 487.1 (M+H).

Reference： [1]Patent: WO2016/57658,2016,A1 .Location in patent: Page/Page column 42; 44
[2]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 935 - 940

74
[ 3132-99-8 ]
[ 25542-62-5 ]
ethyl 6-(3-formylphenyl)hexanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%		Anhydrous LiCl (1.14 g, 26.89 mmol) was dried in a reaction tube at 160 C. for 20 min under high vacuum. Zn powder (1.75 g, 26.89 mmol) was added under argon and the mixture was dried again at 160 C. under high vacuum. The reaction tube was evacuated and filled with argon three times. THF (15 mL) was added and the Zn was activated with 1,2-dibromoethane (0.06 mL, 0.67 mmol) and TMSCl (0.017 mL, 0.13 mmol). Ethyl 6-bromohexanoate (3 g, 13.45 mmol) was added and the reaction mixture was stirred at 55 C. overnight. The solution 1 was carefully separated from excess zinc using a dry syringe. 3-bromobenzaldehyde (1.5 g, 8.1 mmol) was dissolved in THF (5 mL). Pd2(dba)3 (0.074 g, 0.08 mmol) and t-Bu3P (0.162 mL, 0.162 mmol, 1M) was added. The solution of the organozincate compound 1 in THF (1.5 equivalent) was added to the reaction. The mixture was stirred for 30 min at it (room temperature) and then quenched with NH4Cl (aq. sat.: aqueous saturated solution). The mixture was extracted with Et2O. The combined organic phase was dried, concentrated and purified by flash chromatography to give the ester 2 (1.95 g, 7.858 mmol, 97%). 1H NMR (250 MHz, CDCl3): delta=9.96 (s, 1H), 7.60-7.72 (m, 2H), 7.37-7.46 (m, 2H), 4.08 (q, J=7.1 Hz, 2H), 2.66 (t, J=7.5 Hz, 2H), 2.26 (t, J=7.4 Hz, 2H), 1.56-1.71 (m, 4H), 1.26-1.42 (m, 2H), 1.21 (t, J=7.1 Hz, 3H); HRMS (EI+): [M]+ calculated for C15H20O3, 248.1412. found 248.1413.

Reference： [1]Patent: US2016/297731,2016,A1 .Location in patent: Paragraph 0124-0127
[2]Journal of Medicinal Chemistry,2018,vol. 61,p. 4928 - 4937

75
[ 25542-62-5 ]
[ 121-33-5 ]
ethyl 6-(4-formyl-2-methoxyphenoxy)hexanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 18h;	A mixture of vanillin (6.5 g, 42.7 mmol), <strong>[25542-62-5]ethyl 6-bromohexanoate</strong> (8.0 mL, 45.0 mmol)and potassium carbonate (8.70 g, 63.0 mmol) in N,N-dimethylformaldehyde (o mL)was stirred at room temperature for i8h. The reaction mixture was diluted with water(100 mL), separated and extracted with ethyl acetate (120 mL). The combined organicextracts were sequentially washed with water (100 mL), brine (100 mL), dried over magnesium sulfate, filtered and concentrated to give the title compound as a pale yellow oil (12.5 g, 99%). The product was carried through to the next step without any further purification.1H NMR (400 MHz, CDC13) 59.84 (s, 1H), 7.42-7.44 (dd, J=8.2, 1.9 Hz, 1H), 7.40 (d,J=l.9 Hz, 1H), 6.96 (d, J=8.i Hz, 1H), 4.08-4.15 (m, 4H), 3.92 (s, 3H), 2.34 (t, J=7.sHz, 2H), 1.87-1.94 (m, 2H), 1.68-1.75 (m, 2H), 1.49-1.56 (m, 2H), 1.25 (t, J=7.2 Hz, 3H);MS (ES+): m/z = 317 (M+Na) LCMS (Method B): tR = 3.82 mm.
99%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 18h;	A solution of vanillin (6.50 g, 42.7 mmol), <strong>[25542-62-5]ethyl 6-bromohexanoate</strong> (8.00 mL, 45.0 mmol) and potassium carbonate (8.70 g, 63.0 mmol) in AyV-dimethylformamide (50 mL) was stirred at room temperature for 18 h. The reaction mixture was then diluted with water (100 mL), separated and extracted with ethyl acetate (120 mL). The combined organic extracts were sequentially washed with water (100 mL), brine (100 mL), dried over magnesium sulfate, filtered and concentrated to give the title compound (12.5 g, 99%) as a yellow oil, which was carried through to the next step without any further purification. NMR (400 MHz, CDCI3) delta 9.84 (s, lH), 7.43 (dd, J=8.i, 1.9 Hz, lH), 7.40 (d, J=i.9 Hz, lH), 6.96 (d, J=8.i Hz, lH), 4.08-4.15 (m, 4H), 3-9 (s, 3H), 2.34 (t, J=7-5 Hz, 2H), 1.87-1.94 (m, 2H), 1.68-1.75 (m, 2H), 1.49-1.56 (m, 2H), 1.25 (t, J=7.2 Hz, 3H); MS M/Z (EIMS) = 317 (M+Na)+; LCMS (Method B): tR = 3.82 min.

Reference： [1]Patent: WO2017/32983,2017,A1 .Location in patent: Page/Page column 87
[2]Patent: WO2017/194960,2017,A1 .Location in patent: Page/Page column 172-173

76
[ 25542-62-5 ]
[ 118-58-1 ]
benzyl 2-(6-ethoxy-6-oxohexyloxy)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With potassium carbonate; In acetonitrile;Reflux;	General procedure: The corresponding alkyl bromide (2.0eq) and potassium carbonate (2.0eq) were added to a solution of benzyl 2-hydroxybenzoate (1.0eq) in CH3CN, and the mixture was refluxed. After completion of the reaction, the residue was purified by silica gel column chromatography (EtOAc/Hexane) to afford the product.

Reference： [1]Bioorganic and Medicinal Chemistry,2017,vol. 25,p. 3677 - 3684

77
[ 25542-62-5 ]
[ 2233-18-3 ]
ethyl 6-(4-formyl-2,6-dimethylphenoxy)hexanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium carbonate In acetonitrile at 80℃; for 24h;	ethyl 4-(4-formyl-2,6-dimethylphenoxy)butanoate (14aa) General procedure: 4-hydroxy-3,5-dimethylbenzaldehyde(13a)(1.5 g, 10 mmol) and ethyl4-bromobutanoate (1.95g, 10mmol) were dissolved in acetonitrile (100 mL) andtreated with K2CO3 (5.52g, 40mmol). The reaction mixturewas stirred at 80 °C for 24 h.Water was added to thereaction,and the aqueouslayer was extracted with EA (3 × 20 mL). The organic layers were combined,washed with water (3 × 25 mL),dried over anhydrous Na2SO4,and concentrated in vacuo to give compound 14aa(1.87g,71%).
	With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 80℃; for 4h;	4.2.1 Synthesis of intermediate 3 To a solution of 4-hydroxy-3,5-dimethylbenzaldehyde (1) (25mmol) in DMF (60mL), K2CO3 (50mmol) and catalytic amount potassium iodide were added, and the resulting mixture was allowed to warm up for 4h at 80°C. Upon the starting material was consumed completely, the hot reaction suspension was poured into 50mL water, extracted with dichloromethane (3×50mL). The combined organic layers were washed with saturated aqueous sodium bicarbonate and brine, and then dried over anhydrous sodium sulfate. After removing the solvent under reduced pressure to give the crude oil. The crude oil was purified by silica sel flash chromatography (dichloromethane/methanol 50:1) as a colorless oil, yield 82-93%

Reference： [1]Shao, Mingfeng; He, Linhong; Zheng, Li; Huang, Lingxiao; Zhou, Yuanyuan; Wang, Taijing; Chen, Yong; Shen, Mingsheng; Wang, Fang; Yang, Zhuang; Chen, Lijuan [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 17, p. 4051 - 4055]
[2]Yao, Dahong; Li, Chenyang; Jiang, Jin; Huang, Jian; Wang, Jinhui; He, Zhendan; Zhang, Jin [European Journal of Medicinal Chemistry, 2020, vol. 205]

78
[ 13472-81-6 ]
[ 25542-62-5 ]
C₁₁H₁₃Br₂NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%		Weigh 200 mg (0.79 mmol) of 3,5-dibromo-2-hydroxy pyridine then added to 352.53 mg (1.58 mmol) of ethyl 6-bromohexanoateand an appropriate amount of anhydrous K2CO3, and the mixture was dissolved in 2 mL of dimethyl amide at 100 C for 5 h; the 1570 mg (37.5 mmol) of LiOH * H2O was weighed into 50 ml of a mixture of 1,4-dioxane and water (1: 1 by volume) and hydrolyze the synthetic material for 24 h; From Separation and purification obtained a pale yellow crystalline hapten C11H13Br2NO3 138 mg, the yield was 93%.

Reference： [1]Patent: CN105884609,2016,A .Location in patent: Page/Page column 5; 9

79
[ 25542-62-5 ]
[ 59817-32-2 ]
C₁₈H₂₈N₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 60℃; for 24h;	3(10 G, 0.056 mol), 6-bromohexanoate (12.5 g, 0.056 mol)) and diisoimidolethylamine (14.5 g, 0.112 mol) in 100 mL of acetonitrile and stirred at 60. The reaction was allowed to react for 24 hours and then cooled at room temperature. The reaction was poured into water and extracted with methylene chloride. After removing moisture from magnesium sulfate and filtering the solid, the filtrate was concentrated and column purified (13 g, 72%)

Reference： [1]Patent: KR2018/83806,2018,A .Location in patent: Paragraph 0389; 0397-0401

80
[ 40314-06-5 ]
[ 25542-62-5 ]
6-(5-methyl-1,3-dioxo-isoindol-2-yl)hexanoic acid [ No CAS ]

Reference： [1]Patent: EP2045239,2009,A1

81
[ 109-69-3 ]
[ 25542-62-5 ]
[ 2920-38-9 ]
[ 37909-95-8 ]
trans-4-butyl-1-(6-ethoxy-6-oxohexyl)-4-phenylcyclohexa-2,5-dienecarbonitrile [ No CAS ]
cis-4-butyl-1-(6-ethoxy-6-oxohexyl)-4-phenylcyclohexa-2,5-dienecarbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
14%Spectr.		General procedure: To a suspension of the DA 12- sodium salt, butyl chloride or cyclohexyl bromide (1 equiv.) was added dropwise at -40 C and the reaction mixture was kept at the same conditions for 40÷60 min. Afterwards required alkyl bromide (1.1÷1.4 equiv.) was added (Table 1, entries 2÷5) and reaction mixture was treated as described above for dienone 2.

Reference： [1]Tetrahedron,2018,p. 842 - 851

82
[ 25542-62-5 ]
[ 617-05-0 ]
ethyl 4-(6-ethoxy-6-oxohexyloxy)-3-methoxybenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere; Schlenk technique;	A mixture of <strong>[617-05-0]ethyl 4-hydroxy-3-methoxybenzoate</strong> 9 (5.0 g,25.51 mmol), potassium carbonate (10.5 g, 76.5 mmol) and ethyl 6-bromohexanoate (6.8 g, 30.6 mmol) in DMF (20 mL) was stirred overnightat rt. The reaction mixture was filtered and concentrated in vacuum.The residue was dissolved in dichloromethane, and washed withbrine. The organic layer was dried over magnesium sulfate, filtered andconcentrated to yield derivative 10. Yield 8.6 g, 99%; 1H NMR(400 MHz, DMSO-d6) delta 1.18 (t, 3H, J=7.0 Hz), 1.31 (t, 3H,J=7.0 Hz), 1.44-1.40 (m, 2H), 1.63-1.56 (m, 2H), 1.78-1.71 (m, 2H),2.31 (t, 3H, J=7.4 Hz), 3.82 (s, 3H), 4.08-4.00 (m, 4H), 4.28 (q, 2H,J=7.2 Hz), 7.04 (d, 1H, J=8.4 Hz), 7.44 (d, 1H, J=1.8), 7.56 (dd,1H, J1=8.5 Hz, J2=2.0 Hz); 13C NMR (100 MHz, DMSO-d6) delta 172.8,165.4, 152.3, 148.5, 123.0, 121.9, 111.9 (2C), 68.1, 60.3, 59.6, 55.5,33.4, 28.2, 25.0, 24.2, 14.2, 14.0; HR-MS m/z 339.1797 (calcd forC18H27O6 [M+H]+, 339.1802).

Reference： [1]Bioorganic Chemistry,2019,vol. 84,p. 51 - 62

83
[ 25542-62-5 ]
[ 446-72-0 ]
6-((5-hydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl)oxy)hexanoic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%		The genistein (2.0g, 7.4mmol) and KOH (0.415g, 7.4mmol) dissolved in DMF,The reaction was carried out at 60 C for 1 h.Further ethyl 6-bromohexanoate (2.62 mL, 14.8 mmol) and KI (122.8 mg, 0.74 mmol) were added.The reaction is 4 to 6 hours.Pour the reaction solution into a small amount of distilled water, filter the filter cake by suction, and purify by silica gel column chromatography.A pale yellow solid was obtained.Yield: 79%.

Reference： [1]Patent: CN109897024,2019,A .Location in patent: Paragraph 0019

84
[ 25542-62-5 ]
[ 5299-60-5 ]

Yield	Reaction Conditions	Operation in experiment
82.2%	With formic acid; triethylamine; at 50℃;Cooling with ice;	Add 1.56g (7.96mmol) of ethyl 6-bromohexanoate (ie compound 3) to a round bottom flask, place in an ice bath, add 3.79g (31.84mmol) of formic acid, and then slowly add three Ethylamine.After the dropwise addition was completed, the reaction was heated to 50 C overnight.After adding brine, the mixture was extracted with ethyl acetate, and the organic phase was washed with water, 1 mol / L hydrochloric acid, saturated sodium carbonate, and brine.After the sodium sulfate was dried, the solvent was spun off, and the crude product was directly used for the next reaction; that is, methanol and 1 drop of concentrated hydrochloric acid were directly added, and the reaction was performed at room temperature for 2 h. The organic phase was obtained by washing with saturated sodium carbonate, washing with water and washing with brine, drying, spinning off the solvent, and purifying by TLC to obtain the product. Compound 4 was obtained in a yield of 82.2%.

Reference： [1]Patent: CN110698515,2020,A .Location in patent: Paragraph 0098; 0101; 0104

85
[ 25542-62-5 ]
[ 1047-16-1 ]
6-(12-methyl-7,14-dioxo-2,9-disulfo-12,14-dihydroquinolino[2,3-b]acridin-5(7H)-yl)hexanoic acid [ No CAS ]

Reference： [1]Chemistry - A European Journal,2020

86
[ 25542-62-5 ]
[ 1047-16-1 ]
[ 74-88-4 ]
ethyl 6-(12-methyl-7,14-dioxo-12,14-dihydroquinolino[2,3-b]acridin-5(7H)-yl)hexanoate [ No CAS ]

Reference： [1]Chemistry - A European Journal,2020

87
[ 25542-62-5 ]
[ 6278-92-8 ]
ethyl 6-(2',5'-dioxospiro[fluorene-9,4'-imidazolidine]-1'-yl)hexanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86.7%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 12h;	General procedure: A mixture of the imidazolidinedione 2 (1.251g, 5mmol), (5.5mmol) of an appropriate ester [methyl 4-bromomethyl benzoate (1.259g), ethyl bromoacetate (0.918g), ethyl 3-bromopropanoate (0.995g), ethyl 4-bromobutyrate (1.073g), <strong>[25542-62-5]ethyl 6-bromohexanoate</strong> (1.228g) and anhydrous potassium carbonate (1.382g, 10mmol) in DMF (20mL) was allowed to stir at room temperature for 12 hrs. The reaction mixture was diluted with ice water and the resulting precipitate was filtered, washed with water and dried. The crude product was purified by crystallization from aqueous ethanol to form the corresponding compound (3a-e).

Reference： [1]Bioorganic Chemistry,2020,vol. 101

88
[ 4166-53-4 ]
[ 25542-62-5 ]
C₁₃H₂₄O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With [2,2]bipyridinyl; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; zinc In N,N-dimethyl acetamide at 80℃; for 12h;	31 Example 1 General procedure: In the glove box, bis-(1,5-cyclooctadiene)nickel (8.3mg, 0.03mmol) and 2,2'-bipyridine, which is the chemical structural formula structural formula L1, (7.0mg, 0.045mmol) into the microwave tube,Add 0.225mL N,N-dimethylacetamide for coordination for one hour, add zinc powder (39.2mg, 0.6mmol, 2.0 equivalent) into the microwave tube,Then add succinic anhydride (0.45mmol, 1.5eq) and 1-bromooctane (0.3mmol, 1.0eq), cover it and take it out from the glove box, reflux at 80 for 12 hours,Cool to room temperature, uncap and add three drops of water to quench the reaction, remove the solvent under reduced pressure,The crude product is separated by column chromatography (petroleum ether: ethyl acetate = 5:1) to obtain 11 alkanic acid (47.0 mg, 84% yield).

Reference： [1]Current Patent Assignee: NANJING TECH UNIVERSITY - CN111533649, 2020, A Location in patent: Paragraph 0028-0032; 0065

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[ CAS No. 25542-62-5 ] {[proInfo.proName]}

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[ 25542-62-5 ] Synthesis Path-Upstream 1~12

[ 25542-62-5 ] Synthesis Path-Downstream 1~88

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[ 25542-62-5 ]