[ CAS No. 637-59-2 ] {[proInfo.proName]}

Name: 637-59-2|(3-Bromopropyl)benzene|95%
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Quality Control of [ 637-59-2 ]

COA NMR CNMR HPLC LC-MS

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Product Citations

Structure-activity studies of PTPRD phosphatase inhibitors identify a 7-cyclopentymethoxy illudalic acid analog candidate for development

Henderson, Ian M. ; Zeng, Fanxun ; Bhuiyan, Nazmul H. , et al. Biochem. Pharmacol.,2022,195,114868. DOI: 10.1016/j.bcp.2021.114868 PubMed ID: 34863978

Abstract: Interest in development of potent, selective inhibitors of the phosphatase from the receptor type protein tyrosine phosphatase PTPRD as antiaddiction agents is supported by human genetics, mouse models and studies of our lead compound PTPRD phosphatase inhibitor, 7-butoxy illudalic acid analog 1 (7-BIA). We now report structure-activity relationships for almost 70 7-BIA-related compounds and results that nominate a 7- cyclopentyl methoxy analog as a candidate for further development. While efforts to design 7-BIA analogs with substitutions for other parts failed to yield potent inhibitors of PTPRDs phosphatase, ten 7-position substituted analogs displayed greater potency at PTPRD than 7-BIA. Several were more selective for PTPRD vs the receptor type protein tyrosine phosphatases S, F and J or the nonreceptor type protein tyrosine phosphatase N1 (PTPRS, PTPRF, PTPRJ or PTPN1/PTP1B), phosphatases at which 7-BIA displays activity. In silico studies aided design of novel analogs. A 7-position cyclopentyl methoxy substituted 7-BIA analog termed NHB1109 displayed 600-700 nM potencies in inhibiting PTPRD and PTPRS, improved selectivity vs PTPRS, PTPRF, PTPRJ or PTPN1/PTP1B phosphatases, no substantial potency at other protein tyrosine phosphatases screened, no significant potency at any of the targets of clin.-useful drugs identified in EUROFINS screens and significant oral bioavailability. Oral doses up to 200 mg/kg were well tolerated by mice, though higher doses resulted in reduced weight and apparent ileus without clear organ histopathol. NHB1109 provides a good candidate to advance to in vivo studies in addiction paradigms and toward human use to reduce reward from addictive substances.

Keywords: Receptor type protein tyrosine phosphatase ; Cell adhesion molecule ; Addiction ; Drug reward ; Opiates ; Stimulants

Purchased from AmBeed: 37595-74-7 ; 637-59-2 ; 103-63-9 ; 64473-35-4 ; 20443-99-6 ; 939-26-4 ; 3814-32-2 ; 3814-30-0 ; 36881-42-2 ; 17247-58-4 ; 589-15-1 ; 2550-36-9 ; 7051-34-5 ; 161043-38-5 ; 161395-96-6 ; 59311-24-9 ; 78358-86-8 ; 83642-03-9 ...More

Product Details of [ 637-59-2 ]

CAS No. :	637-59-2	MDL No. :	MFCD00000257
Formula :	C₉H₁₁Br	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XMZQWZJMTBCUFT-UHFFFAOYSA-N
M.W :	199.09	Pubchem ID :	12503
Synonyms :

Calculated chemistry of [ 637-59-2 ] Expand+

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	3
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	48.89
TPSA :	0.0 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.87 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.45
Log Po/w (XLOGP3) :	3.72
Log Po/w (WLOGP) :	3.01
Log Po/w (MLOGP) :	3.71
Log Po/w (SILICOS-IT) :	3.51
Consensus Log Po/w :	3.28

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.66
Solubility :	0.0432 mg/ml ; 0.000217 mol/l
Class :	Soluble
Log S (Ali) :	-3.41
Solubility :	0.0772 mg/ml ; 0.000388 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.47
Solubility :	0.00678 mg/ml ; 0.000034 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.45

Safety of [ 637-59-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 637-59-2 ]

* 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 [ 637-59-2 ]
Downstream synthetic route of [ 637-59-2 ]

[ 637-59-2 ] Synthesis Path-Upstream 1~8

1
[ 637-59-2 ]
[ 64473-35-4 ]
[ 54877-27-9 ]

Reference： [1] Chemical Science, 2017, vol. 8, # 10, p. 7009 - 7013

2
[ 637-59-2 ]
[ 1068-90-2 ]
[ 34993-02-7 ]

Yield	Reaction Conditions	Operation in experiment
83%	With hydrogenchloride; ammonium hydroxide; sodium ethanolate; sodium In ethanol	EXAMPLE 5 (+-)-2-Amino-5-phenylpentanoic acid Diethyl acetamidomalonate (220 g) in 1 L of absolute ethanol was added to a stirred solution of sodium ethoxide in ethanol, prepared by dissolving sodium (24 g) in absolute ethanol (500 mL), under nitrogen. The reaction mixture was refluxed under nitrogen for 30 minutes and then 1-bromo-3-phenylpropane (200 g) was added. The reaction mixture was refluxed overnight, cooled to ambient temperature, the precipitate removed by filtration and the solvent removed in vacuo. Concentrated hydrochloric acid (800 mL) was added to the residue and the reaction mixture was refluxed for 14 hours. The cooled aqueous solution was washed with ether (2*200 mL). The residual ether in the aqueous phase was removed by nitrogen bubbling through the solution. The pH of the aqueous phase was adjusted to 7-8 by the addition of ammonium hydroxide. The title compoundcompound was collected by filtration, air dried and recrystallized from ethanol-water to afford 150 g (83percent). m.p. 255°-257° C. MS (FAB) m/e 194 (M+H)⁺.

Reference： [1] Patent: US5663148, 1997, A,

3
[ 637-59-2 ]
[ 5560-59-8 ]

Reference： [1] Patent: CN103508898, 2016, B,

4
[ 637-59-2 ]
[ 62777-25-7 ]

Reference： [1] Journal of Organic Chemistry, 1990, vol. 55, # 21, p. 5567 - 5571
[2] Bulletin of the Chemical Society of Japan, 1976, vol. 49, p. 3280 - 3284

5
[ 637-59-2 ]
[ 61897-33-4 ]
[ 67469-78-7 ]

Reference： [1] European Journal of Medicinal Chemistry, 1980, vol. 15, # 4, p. 363 - 370

6
[ 637-59-2 ]
[ 67469-78-7 ]

Reference： [1] Organic Process Research and Development, 2002, vol. 6, # 5, p. 621 - 627

7
[ 637-59-2 ]
[ 113100-86-0 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 4, p. 523 - 528
[2] Patent: CN102757444, 2016, B,

8
[ 637-59-2 ]
[ 165377-43-5 ]

Reference： [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 9, p. 3478 - 3491

[ 637-59-2 ] Synthesis Path-Downstream 1~109

1
[ 7597-56-0 ]
[ 637-59-2 ]
[ 101115-21-3 ]

Reference： [1]Journal of Organic Chemistry,1957,vol. 22,p. 1704

2
[ 637-59-2 ]
[ 20035-08-9 ]
(3-(ethylsulfonyl)propyl)benzene [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1955,vol. 20,p. 996,999

3
[ 637-59-2 ]
[ 1600-27-7 ]
[ 122-72-5 ]

Reference： [1]Tetrahedron,1974,vol. 30,p. 2467 - 2475

4
[ 637-59-2 ]
[ 1068-90-2 ]
[ 52161-73-6 ]

Yield	Reaction Conditions	Operation in experiment
98%		A solution of sodium ethoxide was generated by the addition of sodium metal (52.89 grams, 2.3007 mol), over 3 hours, to ethanol (1500 mL). To the sodium ethoxide solution, at ambient temperature, was added a solution of diethylacetamidomalonate (499.75 grams, 2.3007 mol) dissolved in ethanol (225 mL). The reaction mixture was stirred for 1.5 hours at ambient temperature. 1-bromo-3-phenylpropane (458.07 grams, 2.3007 mol) was then added over 15 minutes and the reaction mixture was refluxed until complete as determined by HPLC (16 hours). The reaction mixture was concentrated to dryness and the residue partitioned between ethyl acetate (1×1500 mL and 2×500 mL) and water (1500 mL). The ethyl acetate layers were combined, washed with saturated sodium chloride solution (4×500 mL), dried using sodium sulfate, and concentrated to give 752.1 grams (98%) of the above-identified product as a light yellow solid: A 1.0 gram sample was recrystallized from hexane:ethyl acetate (19:1, v:v) to give a mp 84-86 C. [00126] 1H nmr (CDCl3): delta 1.18-1.23 (t, 6H), 1.37-1.50 (m, 2H), 2.02 (s, 3H), 2.34-2.41 (m, 2H), 2.58-2.62 (t, 2H), 4.16-4.24 (q, 4H), 6.76 (s, broad, 1H), 7.11-7.28 (m, 5H). 13C nmr (CDCl3): delta 13.95, 23.03, 25.67, 31.85, 35.45, 62.46, 66.49, 125.40, 125.90, 128.27, 128.35, 141.77, 168.11, 168.94. MS (FIA ) m/z 336.3 ([M+H]+). IR (KBr, cm-1) 1645.98 (amide), 1744.76 (CO). Anal. Calc'd. for C18H25NO5: C, 64.46; H, 7.51; N, 4.17. Found: C, 64.60; H, 7.37; N, 4.39.
	With sodium ethanolate; sodium; In ethanol; nitrogen;	(1) Sodium (0.23 g) was added to 15 ml of absolute ethanol and the mixture was stirred at room temperature for 30 minutes in a nitrogen flow to give a 10 mmol solution of sodium ethoxide in ethanol. To this solution, 1.98 g of diethyl 2-acetamidomalonate was added and the mixture was heated at 50 C. for 30 minutes in a stream of nitrogen. 3-Phenylpropyl bromide was added thereto at room temperature and the mixture was refluxed under heating for 24 hours. The mixture was neutralized with dilute hydrochloric acid and ethanol was distilled away. The resultant residue was extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled away and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4-1:1) and recrystallized from diisopropyl ether-hexane to give 800 mg of diethyl 2-acetamido-2-(3-phenylpropyl)malonate as white crystals. melting point=76-77 C. Rf: 0.58 (ethyl acetate:hexane=1:1) 1 H-NMR (90 MHz, CDCl3) delta: 1.22 (3H, t, J=7 Hz), 1.10-1.56 (4H, m), 2.02 (3H, s), 2.28-2.75 (2H, m), 4.21 (4H, q, J=7 Hz), 6.75 (1H, br.s), 7.02-7.42 (5H, m) IRnu: 3259, 2980, 2863, 1738, 1648 cm-1 MS(EI): 335(M+)
		A solution of 21 % sodium ethoxide in ethanol (410 g, 1.266 mol) was added to a solution of diethylacetamidomalonate (250 g, 1.151 mol) dissolved in ethanol (915 mL). The reaction mixture was stirred for 2 hours at ambient temperature. 1-brom-3- phenylpropane (229.1 grams, 1.151 mol) was then added over 15 minutes and the reaction mixture was stirred at 73 C until complete as determined by HPLC (28 hours). The reaction mixture was solvent exchanged to ethyl acetate (1500 mL) and washed with water (1500 mL). The water layer was extract3ed with ethyl acetate (1 x 750 mL). The combined layers were washed with saturated sodium chloride solution (1 x 750 mL). The ethyl acetate solution was solvent exchanged to heptane and diluted to give a slurry volume of 3000 mL. The solids were filtered and washed with heptane (625 mL) to give 313 grams of 451840 at 95% purity (775) as a tan solid.'H nmr (CDC13) : 8 1. 18-1. 23 (t, 6H), 1. 37-1.50 (m, 2H), 2.02 (s, 3H), 2.34-2. 41 (m, 2H), 2.58-2. 62 (t6,2H), 4.16-4. 24 (q, 4H), 6.76 (s, broad, 1H), 7.11-7. 28 (m, 5H).

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 6748 - 6762
[2]Patent: US6828331,2004,B1 .Location in patent: Page column 25
[3]Bulletin of the Chemical Society of Japan,1976,vol. 49,p. 3280 - 3284
[4]Patent: US5604229,1997,A
[5]Patent: WO2003/87036,2003,A1 .Location in patent: Page/Page column 8-9

5
[ 25077-25-2 ]
[ 637-59-2 ]
[ 147767-29-1 ]

Reference： [1]Heterocycles,1993,vol. 36,p. 71 - 78

6
[ 67686-01-5 ]
[ 637-59-2 ]
1-Benzyl-4-(3-phenyl-propoxymethyl)-piperidine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 4344 - 4361

7
[ 1618-26-4 ]
[ 637-59-2 ]
[ 129169-38-6 ]

Reference： [1]Tetrahedron,1990,vol. 46,p. 2111 - 2128

8
[ 637-59-2 ]
[ 14489-75-9 ]
[ 98977-55-0 ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 112 - 125

9
[ 637-59-2 ]
[ 83511-07-3 ]
[ 83487-54-1 ]

Reference： [1]Journal of the American Chemical Society,1982,vol. 104,p. 7196 - 7204

10
[ 637-59-2 ]
[ 61897-33-4 ]
[ 67469-78-7 ]

Reference： [1]European Journal of Medicinal Chemistry,1980,vol. 15,p. 363 - 370

11
[ 2859-68-9 ]
[ 637-59-2 ]
3-phenylpropyl-3-(2-pyridyl)propyl ether [ No CAS ]

Reference： [1]Archiv der Pharmazie,1995,vol. 328,p. 445 - 450

12
[ 2307-69-9 ]
[ 637-59-2 ]
[ 124-18-5 ]
[ 112-95-8 ]
[ 4215-86-5 ]

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 2125 - 2133

13
[ 637-59-2 ]
[ 715-11-7 ]
[ 124-18-5 ]
[ 112-95-8 ]
[ 63213-07-0 ]

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 2125 - 2133

14
[ 637-59-2 ]
[ 599-91-7 ]
[ 1077-16-3 ]

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 2125 - 2133

15
[ 637-59-2 ]
[ 4119-41-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium iodide In acetone for 6h; Reflux;
97%	With sodium iodide In acetone Reflux;
95%	With potassium iodide In acetone for 2h; Reflux;

95%	With sodium iodide In acetone at 20℃; for 16h; Inert atmosphere;
83%	With sodium iodide In acetone Reflux;
63%	With sodium iodide In acetone at 20℃; for 20h;
	With sodium iodide In butanone
	With sodium iodide In acetone at 20℃; Inert atmosphere; Reflux;
	With sodium iodide In acetone for 6h; Reflux;
	Multi-step reaction with 2 steps 1: Caswell No_. 744A / N,N-dimethyl-formamide / 18 h / 80 °C / Inert atmosphere 2: tert-Butyl iodide / dichloromethane / 18 h / 20 °C / Inert atmosphere

Reference： [1]Wang, Xiaoling; Ji, Xiaoming; Shao, Changdong; Zhang, Yu; Zhang, Yanghui [Organic and Biomolecular Chemistry, 2017, vol. 15, # 26, p. 5616 - 5624]
[2]Bouillon, Jean-Philippe; Couve-Bonnaire, Samuel; Pannecoucke, Xavier; Xiao, Pan [Advanced synthesis and catalysis, 2020, vol. 362, # 4, p. 949 - 954]
[3]Bekere, Laura; Lokshin, Vladimir; Sigalov, Mark; Gvishi, Raz; Zhao, Peng; Hagan, David J.; Van Stryland, Eric W.; Khodorkovsky, Vladimir [New Journal of Chemistry, 2016, vol. 40, # 2, p. 1143 - 1148]
[4]Koo, Seung Moh; Vendola, Alex J.; Momm, Sarah Noemi; Morken, James P. [Organic Letters, 2020, vol. 22, # 2, p. 666 - 669]
[5]Li, Songyi; Lian, Chang; Mo, Fanyang; Qiu, Di; Yue, Guanglu; Zhang, Jianning [Journal of Organic Chemistry, 2022, vol. 87, # 6, p. 4291 - 4297]
[6]Wempe [Journal of Molecular Structure, 2001, vol. 562, # 1-3, p. 63 - 78]
[7]Ornstein, Paul L.; Bleisch, Thomas J.; Arnold, M. Brian; Wright, Rebecca A.; Johnson, Bryan G.; Schoepp, Darryle D. [Journal of Medicinal Chemistry, 1998, vol. 41, # 3, p. 346 - 357]
[8]Madsen, Andreas S.; Kristensen, Helle M. E.; Lanz, Gyrithe; Olsen, Christian A. [ChemMedChem, 2014, vol. 9, # 3, p. 614 - 626]
[9]Shen, Peng-Xiang; Wang, Xiao-Chen; Wang, Peng; Zhu, Ru-Yi; Yu, Jin-Quan [Journal of the American Chemical Society, 2015, vol. 137, # 36, p. 11574 - 11577]
[10]Maury, Julien; Feray, Laurence; Bertrand, Michele P.; Kapat, Ajoy; Renaud, Philippe [Tetrahedron, 2012, vol. 68, # 47, p. 9606 - 9611,6]

16
[ 637-59-2 ]
[ 100-49-2 ]
(3-cyclohexylmethoxy-propyl)-benzene [ No CAS ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 1843 - 1846

17
[ 637-59-2 ]
[ 13737-04-7 ]
2-pyridyldimethyl(4-phenylbutyl)silane [ No CAS ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 5537 - 5540
[2]Journal of Organic Chemistry,2001,vol. 66,p. 3970 - 3976

18
[ 4138-26-5 ]
[ 637-59-2 ]
[ 259268-48-9 ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 205 - 213

19
[ 637-59-2 ]
[ 245-08-9 ]
1-(3-phenylpropyl)-δ-carbolinium bromide [ No CAS ]

Reference： [1]Medicinal Chemistry Research,1999,vol. 9,p. 118 - 132

20
[ 637-59-2 ]
[ 127-09-3 ]
[ 122-72-5 ]

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 2027 - 2029

21
[ 2142-06-5 ]
[ 637-59-2 ]
[ 159757-35-4 ]

Reference： [1]Tetrahedron,2003,vol. 59,p. 3369 - 3378

22
[ 442-51-3 ]
[ 637-59-2 ]
3-(7-methoxy-1-methyl-β-carbolin-9-yl)-1-phenylpropane [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 4613 - 4623
[2]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 6558 - 6561
[3]European Journal of Medicinal Chemistry,2013,vol. 60,p. 135 - 143
[4]European Journal of Medicinal Chemistry,2018,vol. 147,p. 253 - 265

23
[ 486-60-2 ]
[ 637-59-2 ]
5-(3-phenylpropoxy)psoralen [ No CAS ]

Reference： [1]Molecular Pharmacology,2004,vol. 65,p. 1364 - 1374

24
[ 39512-49-7 ]
[ 637-59-2 ]
VUF 5745 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With sodium carbonate; sodium iodide; In acetonitrile; for 2h;Reflux; Inert atmosphere;	General procedure: Sodium carbonate (372 mg, 3.51 mmol) was added to the solution of benzyl bromide (5a) (300 mg, 1.75 mmol), (p-chlorophenyl)piperidin-4-ol (6) (447 mg, 2.11 mmol) and sodium iodide (316 mg, 2.11 mmol) in dry MeCN (2.0 mL) at room temperature under atmosphere of argon, and the mixture was refluxed for indicated hours. The reaction quenched with water and extracted with CHCl3. The extracts were washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by column chromatography with CHCl3/MeOH (50:1) to give N-benzyl-4-(p-chlorophenyl)piperidin-4-ol (7a) as a yellow oil in 73% yield.
		EXAMPLE 86 4-(4-Chlorophenyl)-4-hydroxyl-1-(3-phenylpropyl)piperidine STR123 From 3-phenylpropyl bromide (200 mg, 1.0 mmol) and <strong>[39512-49-7]4-(4-chlorophenyl)-4-hydroxypiperidine</strong> (212 mg, 1.0 mmol) there was obtained 100 mg (30%) of the amine as a yellowish powder, mp 107-8 C. 1 H NMR (CDCl3): 1.52-1.75(m, 5H), 1.84-1.96 (m, 2H), 2.12-2.19 (m, 2H), 2.40-2.49 (m, 2H), 2.661 (t, 2H, J=7.6), 2.83-2.86 (m, 2H), 7.19-7.33 (m, 6H), 7.43-7.46 (m, 3H). Anal. Calcd. for C20 H24 ClNO: C 72.82, H 7.33, N 4.25; Found: C 72.54, H 7.18, N 4.23.

Reference： [1]Heterocycles,2018,vol. 97,p. 560 - 568
[2]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 7213 - 7230
[3]Patent: US6124323,2000,A

25
[ 637-59-2 ]
[ 64318-28-1 ]
[ 788825-01-4 ]

Yield	Reaction Conditions	Operation in experiment
84%	With potassium carbonate; In N,N-dimethyl-formamide; at 50℃; for 24h;	General procedure: K2CO3 (0.415 g, 3 equiv) and appropriate alkyl bromide 4(1 equiv) were added successively to a solution of tert-butyl2-[(4-hydroxyphenyl)ethyl]carbamate (9) (0.237 g, 1 mmol)in DMF (1.9 ml). The suspension was stirred vigorously(500 rpm) at 50 C for 24 h. Then it was allowed to cooldown to room temperature and quenched with H2O (15.9 ml).The stirring was continued until the formation of precipitatewas completed. After standing at room temperature withoutmixing for 3 h, the resulting precipitate was filtered andwashed successively with H2O (4 ml) and hexane (5 × 4 ml) toobtain the desired compounds 10, which were dried invacuum (10-2 Torr) at 25 C for 2 h.

Reference： [1]Chemistry of Heterocyclic Compounds,2017,vol. 53,p. 341 - 349
Khim. Geterotsikl. Soedin.,2017,vol. 53,p. 341 - 349,9
[2]Journal of Medicinal Chemistry,2006,vol. 49,p. 1101 - 1112

26
[ 16681-56-4 ]
[ 637-59-2 ]
2-bromo-1-(3-phenylpropyl)-1H-imidazole [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2006,vol. 4,p. 268 - 277

27
[ 3034-62-6 ]
[ 637-59-2 ]
2-iodo-1-(3-phenylpropyl)-1H-imidazole [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2006,vol. 4,p. 268 - 277

28
[ 637-59-2 ]
[ 113100-86-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 523 - 528
[2]Patent: CN102757444,2016,B

29
[ 637-59-2 ]
[ 62777-25-7 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 5567 - 5571
[2]Bulletin of the Chemical Society of Japan,1976,vol. 49,p. 3280 - 3284

30
[ 637-59-2 ]
[ 5454-06-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: (i) NaH, DMF, (ii) /BRN= 2205527/ 2: aq. KOH / ethane-1,2-diol / 48 h / Heating
	Multi-step reaction with 2 steps 1.1: sodium / ethanol / 0.5 h / 20 °C 1.2: 24 h / Reflux 2.1: potassium hydroxide / ethanol / 24 h / 0 - 20 °C
	Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 °C 1.2: 12 h / 0 - 20 °C 2.1: sodium hydroxide; water / ethanol / 5 h / 120 °C

Reference： [1]Julia,M.; Chottard,J.-C. [Bulletin de la Societe Chimique de France, 1968, p. 3691 - 3700]
[2]Kokkala, Paraskevi; Voreakos, Kostas; Lelis, Angelos; Patiniotis, Konstantinos; Skoulikas, Nikolaos; Devel, Laurent; Ziotopoulou, Angeliki; Kaloumenou, Eleni; Georgiadis, Dimitris [Molecules, 2022, vol. 27, # 4]
[3]Dong, Kaiwu; Ren, Xinyi; Shen, Chaoren; Wang, Guangzhu [Chemical Communications, 2022, vol. 58, # 8, p. 1135 - 1138]

31
[ 82-07-5 ]
[ 637-59-2 ]
[ 194218-97-8 ]

Yield	Reaction Conditions	Operation in experiment
88%	With n-butyllithium; In tetrahydrofuran; hexane; at 0 - 20℃; for 16.4667h;pH 14.0;	To a solution of 10 g (44 mmol, 1 eq) of 9-xanthenylcarboxylic acid in 200 mL of THF at 0C was added 37.2 mL (93 mmol, 2.1 eq) of a 2.5 M solution of n-butyllithium in hexanes dropwise over 15 min. (First equivalent resulted in precipitation of Li salt of the carboxylate; solution became homogeneous as dianion formed.) The resulting orange solution of dianion was stirred at 0C for 10 min and 9.4 mL (62 mmol, 1.4 eq) of 1-bromo-3-phenylpropane was added quickly over 3 min. The reaction was stirred at 0C and allowed to warm to RT as the ice bath melted. After 16 h, the basic reaction mixture (pH -14) was extracted with water (3 x 100 mL). The combined aqueous layers were acidified (to pH ~1) with 6 N HCl and extracted with ether (3 x 100 mL). The combined ether solutions were dried (MgSO4), filtered and concentrated to afford 17.04 g of a viscous golden oil. The oil was dissolved in hot hexanes using a small amount of CH2Cl2 to effect complete dissolution. Concentration of this solution resulted in a yellow solid which was recrystallized from ether/hexanes to afford' 13.3 g (88%) of title compound as a white crystalline solid, m.p. 137-138C. TLC (silica gel, 10% MeOH in CH2Cl2, UV and I2) Rf = 0.52.
13.3 g (88%)	With n-butyllithium; In tetrahydrofuran;	A. 9-(3-Phenylpropyl)-9H-<strong>[82-07-5]xanthene-9-carboxylic acid</strong> To a solution of 10 g (44 mmol, 1 eq) of 9-xanthenylcarboxylic acid in 200 mL of THF at 0 C. was added 37.2 mL (93 mmol, 2.1 eq) of a 2.5M solution of n-butyllithium in hexanes dropwise over 15 min. (First equivalent resulted in precipitation of Li salt of the carboxylate; solution became homogeneous as dianion formed.) The resulting orange solution of dianion was stirred at 0 C. for 10 min and 9.4 mL (62 mmol, 1.4 eq) of 1-bromo-3-phenylpropane was added quickly over 3 min. The reaction was stirred at 0 C. and allowed to warm to RT as the ice bath melted. After 16 h, the basic reaction mixture (pH ~14) was extracted with water (3100 mL). The combined aqueous layers were acidified (to pH ~1) with 6N HCl and extracted with ether (3100 mL). The combined ether solutions were dried (MgSO4), filtered and concentrated to afford 17.04 g of a viscous golden oil. The oil was dissolved in hot hexanes using a small amount of CH2 Cl2 to effect complete dissolution. Concentration of this solution resulted in a yellow solid which was recrystallized from ether/hexanes to afford 13.3 g (88%) of title compound as a white crystalline solid, m.p. 137-138 C.

Reference： [1]Patent: EP904262,2004,B1 .Location in patent: Page 80
[2]Patent: US5760246,1998,A

32
[ 637-59-2 ]
[ 184151-49-3 ]
[ 201286-92-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In acetone;	REFERENCE EXAMPLE 41 Methyl 3-methyl-1-{3-(phenyl)propyl}-1 H-indole-6-carboxylate A stirred solution of <strong>[184151-49-3]methyl 3-methyl-1 H-indole-6-carboxylate</strong> (0.5 g, Reference Example 30) in acetone (35 ml) was treated with 1-bromo-3-phenylpropane (0.577 g) and sodium hydroxide (0.116 g). The mixture was stirred at room temperature for 12 hours then poured into water (35 ml) and then extracted three times with ethyl acetate (50 ml). The combined extracts were washed with dilute hydrochloric acid (50 ml, 1N) then with saturated sodium bicarbonate solution (50 ml), then dried over magnesium sulphate and then evaporated. The residue was subjected to flash column chromatography on silica eluding with a mixture of ethyl acetate and hexane (50:1, v/v) to yield the title compound (0.58 g).

Reference： [1]Patent: US6303600,2001,B1

33
[ 637-59-2 ]
[ 105526-85-0 ]
[ 5137-55-3 ]
(S)-1-(3-Phenylpropyl)-5-[(trityloxy)-methyl]-2-pyrrolidinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In toluene;	Example II (S)-1-(3-Phenylpropyl)-5-[(trityloxy) methyl]-2-pyrrolidinone 203.7 g of (S)-5-[(trityloxy)methyl]-2-pyrrolidinone, 3 liters of toluene, 1.4 liters of 50% aqueous sodium hydroxide solution, 139.4 g of 3-phenylpropylbromide and 10 g of methyl-trioctyl ammonium chloride are stirred vigorously for 25 hours at ambient temperature under argon. Then 40 ml of 3-phenylpropylbromide are added and the mixture is stirred for a further 24 hours. It is distributed between toluene and water, the organic phase is separated off, dried over magnesium sulphate, then stirred for half an hour with 5 spoons of active charcoal, filtered and concentrated by rotary evaporation. The evaporation residue is chromatographed over a silica gel column with methylene chloride and then with ethyl acetate. The crystalline evaporation residue is then recrystallized from isopropanol/water 4:1. Yield: 234.3 g (86% of theory), Melting point: 103-104 C. Rf value: 0.71 (silica gel; ethyl acetate)

Reference： [1]Patent: US5541343,1996,A

34
[ 637-59-2 ]
[ 1068-90-2 ]
[ 34993-02-7 ]

Yield	Reaction Conditions	Operation in experiment
150 g (83%)	With hydrogenchloride; ammonium hydroxide; sodium ethanolate; sodium; In ethanol;	EXAMPLE 5 (+-)-2-Amino-5-phenylpentanoic acid Diethyl acetamidomalonate (220 g) in 1 L of absolute ethanol was added to a stirred solution of sodium ethoxide in ethanol, prepared by dissolving sodium (24 g) in absolute ethanol (500 mL), under nitrogen. The reaction mixture was refluxed under nitrogen for 30 minutes and then 1-bromo-3-phenylpropane (200 g) was added. The reaction mixture was refluxed overnight, cooled to ambient temperature, the precipitate removed by filtration and the solvent removed in vacuo. Concentrated hydrochloric acid (800 mL) was added to the residue and the reaction mixture was refluxed for 14 hours. The cooled aqueous solution was washed with ether (2*200 mL). The residual ether in the aqueous phase was removed by nitrogen bubbling through the solution. The pH of the aqueous phase was adjusted to 7-8 by the addition of ammonium hydroxide. The title compoundcompound was collected by filtration, air dried and recrystallized from ethanol-water to afford 150 g (83%). m.p. 255-257 C. MS (FAB) m/e 194 (M+H)+.

Reference： [1]Patent: US5663148,1997,A

35
[ 15336-72-8 ]
[ 24424-99-5 ]
[ 637-59-2 ]
1-tert-butoxycarbonyl-1'-(3-phenylpropan-1-yl)-4,4'-bipiperidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; potassium carbonate In tetrahydrofuran; ethanol; ethyl acetate	R.6.1 1) 1) Synthesis of 1-tert-butoxycarbonyl-1'-(3-phenylpropan-1-yl)-4,4'-bipiperidine To a solution of 10.98 g (45.52 mM) of 4,4'-bi-piperidine and 9.06 g (45.5 mM) of 1-bromo-3-phenylpropane in 150 ml of ethanol was added 18.9 g (137 mM) of potassium carbonate and the mixture was stirred at room temperature for one day. This reaction mixture was filtered and the solvent was removed from the filtrate under reduced pressure. The residue was dissolved in 100 ml of tetrahydrofuran, and after 11.9 g (54.6 mM) of di-tert-butyl dicarbonate was added, the mixture was stirred at room temperature for 6 hours. This reaction mixture was poured in aqueous solution of sodium hydroxide and extracted with 3 portions of ethyl acetate. The pooled organic layer was dried over MgSO4 and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 1/1 ethyl acetate) to provide the title compound. Yellow solid. Yield 3.597 g (20%) 1H-NMR (CDCl3, 200 MHz) δ: 1.009-1.381 (6 H, m), 1.451 (9 H, s), 1.628-1.683 (4 H, m), 1.744-1.896 (4 H, m), 2.333 (2 H, t, 7.7 Hz), 2.575-2.689 (4 H, m), 2.946 (2 H, br d, 11.8 Hz), 4.064-4.169 (2 H, m), 7.127-7.305 (5 H, m).

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - US6235731, 2001, B1

36
[ 639068-43-2 ]
[ 637-59-2 ]
cis-1-tert-butoxycarbonyl-3,5-dimethyl-4-(3-phenylpropan-1-yl)piperazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In water; N,N-dimethyl-formamide;	1) Synthesis of cis-1-tert-butoxycarbonyl-3,5-dimethyl-4-(3-phenylpropan-1-yl)piperazine To a suspension of 10 g (46.66 mmol.) of <strong>[639068-43-2]cis-1-tert-butoxycarbonyl-3,5-dimethyl piperazine</strong> and 12.90 g (93.3 mmol.) of potassium carbonate in N,N-dimethylformamide (50 ml) was added, at room temperature, 11.15 g (56 mmol.) of 1-bromo-3-phenylpropane. The mixture was stirred for 40 hours at 120° C., which was then cooled to room temperature. To the reaction system was added water, which was subjected to extraction with ethyl acetate. The organic layer was washed with a saturated aqueous saline solution and dried over magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by means of a column chromatography (ethyl acetate/hexane 20-30percent) to give the object compound as a yellow oily product. The yield was 12.21 g (79percent). 1H-NMR (CDCl3, 200 MHz) delta: 1.00 (6H, d, J=5.8 Hz), 1.45 (9H, s), 1.57-1.69 (2H, m), 2.43-2.62 (6H, m), 2.67-2.85 (2H, s), 3.68-3.96 (2H, m), 7.13-7.35 (5H, m). IR (neat): 2974, 2931, 2856, 1695, 1454, 1427, 1273, 1248, 1174, 1142, 748, 700 cm-1.

Reference： [1]Patent: US6235731,2001,B1

37
[ 23795-02-0 ]
[ 637-59-2 ]
[ 691903-73-8 ]

Yield	Reaction Conditions	Operation in experiment
46%		Reference Example 26 Ethyl 4-(3-phenylpropoxy)benzenepropanoate To a solution of ice-cooled ethyl 4-hydroxybenzenepropanoate (0.40 g, 2.1 mmol) in N,N-dimethylformamide (15 mL) was added 60% sodium hydride (0.11 g, 2.7 mmol), and the mixture was stirred for 30 minutes. Then, 1-bromo-3-phenylpropane (0.53 g, 2.7 mmol) was added thereto, and the mixture was stirred at room temperature for 3 hours. To the reaction solution was added water, and the reaction mixture was extracted with ethyl acetate. The extract was washed with water, dried, and then concentrated. The residue was purified with silica gel column chromatography (hexane/ethyl acetate = 18: 1) to give the title compound (0.29 g, yield 46%).
46%		Reference Example 5 ethyl 4-(3-phenylpropoxy)benzenepropanoate To an ice-cooled solution of ethyl 4-hydroxybenzenepropanoate (0.40 g, 2.1 mmol) in N,N-dimethylformamide (15 mL) was added 60% sodium hydride (0.11 g, 2.7 mmol), and the mixture was stirred for 30 min. 1-Bromo-3-phenylpropane (0.53 g, 2.7 mmol) was added, and the mixture was stirred at room temperature for 3 hrs. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water, dried and concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=18:1) to give the title compound (0.29 g, yield 46%). oil. 1H NMR (CDCl3) delta 1.23 (3H, t, J=7.1 Hz), 2.04-2.13 (2H, m), 2.58 (2H, t, J=8.1 Hz), 2.88 (2H, t, J=8.1 Hz), 3.94 (2H, t, J=6.3 Hz), 4.12 (2H, q, J=7.1 Hz), 6.81 (2H, d, J=8.6 Hz), 7.10 (2H, d, J=8.6 Hz), 7.19-7.31 (5H, m).

Reference： [1]Patent: EP1688138,2006,A1 .Location in patent: Page/Page column 81
[2]Patent: EP1559422,2005,A1 .Location in patent: Page/Page column 71

38
[ 637-59-2 ]
[ 85960-55-0 ]
[ 1009359-50-5 ]

Reference： [1]Synthesis,2007,p. 3886 - 3890

39
[ 2380-86-1 ]
[ 637-59-2 ]
[ 1145779-98-1 ]

Yield	Reaction Conditions	Operation in experiment
59%	With caesium carbonate; In N,N-dimethyl-formamide; at 80℃; for 2h;	The <strong>[2380-86-1]6-hydroxyindole</strong> XII (2.85 g, 21 mmol) is dissolved in 50 ml_ of DMF.7.67 g (23 mmol) of caesium carbonate and 23 mmol of the corresponding halogenated derivative are added. It is heated at 8O0C for 2 h. Allow to cool and filter the reaction crude. Evaporate to dryness under low pressure and dissolve in DCM. Wash with 1 N NaOH. Separate the organic phase, filter and evaporate. The XIII derivatives are thus obtained in solid form.Example when R6 = PhCH2CH2CH2: 3.1 O g are obtained (Yield: 59%). HPLC-MS: Purity 99.9%, M+1 = 251

Reference： [1]Patent: WO2009/53440,2009,A1 .Location in patent: Page/Page column 20

40
[ 637-59-2 ]
[ 135-76-2 ]
[ 1092117-40-2 ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 7486 - 7494

41
[ 637-59-2 ]
[ 87150-13-8 ]
[ 1258619-27-0 ]

Reference： [1]Chemistry - A European Journal,2010,vol. 16,p. 12307 - 12311

42
[ 4414-89-5 ]
[ 637-59-2 ]
[ 1262643-18-4 ]

Reference： [1]Journal of the American Chemical Society,2011,vol. 133,p. 1209 - 1211

43
[ 4414-89-5 ]
[ 637-59-2 ]
[ 1262643-64-0 ]

Reference： [1]Journal of the American Chemical Society,2011,vol. 133,p. 1209 - 1211

44
[ 23709-47-9 ]
[ 637-59-2 ]
[ 1262643-19-5 ]

Reference： [1]Journal of the American Chemical Society,2011,vol. 133,p. 1209 - 1211

45
[ 23709-47-9 ]
[ 637-59-2 ]
[ 1262643-66-2 ]

Reference： [1]Journal of the American Chemical Society,2011,vol. 133,p. 1209 - 1211

46
[ 637-59-2 ]
[ 6972-71-0 ]
[ 1338684-43-7 ]

Yield	Reaction Conditions	Operation in experiment
68%		Preparation of 4,5-dimethyl-2-nitro-N-(3-phenylpropyDanilineTo a 0C solution of <strong>[6972-71-0]4,5-dimethyl-2-nitroaniline</strong> (3.0 g, 0.018 mol) in dry DMF (80 mL) is added sodium hydride (722 mg, 0.0180 mol) portion wise (gas evolution). After 15 min., the cooling bath is removed and solution is stirred 30 min. at rt. To this solution is added l-bromo-3-phenylpropane (3.29 mL, 0.0217 mol) dropwise via syringe. After 18 h at rt, the reaction is concentrated in vacuo to remove DMF and the residue partitioned between DCM and saturated ammonium chloride solution (200 mL each). The layers are separated, the aqueous layer is extracted with DCM (3 x lOOmL), and the organics are combined, dried with anhydrous sodium sulfate and concentrated. The residue is subjected to silica gel chromatography (230-400 mesh, 350 g, elution with 5% EtOAc/hexane) to give 3.51 g (68%) of the desired product as an orange oil. NMR (400 MHz, CDCI3) delta 2.06 (2 H, m), 2.18 (3 H, s), 2.24 (3 H, s), 2.78 (2 H, t), 3.30 (2 H, t), 6.54 (1 H, s), 7.23 (3 H, m), 7.31 (2 H, m), 7.93 (1 H, s), 8.04 (1 H, br s); MS (ESI+) for Ci7H2oN202 m/z 285.2 (M+H)+, HPLC retention time: 5.54 min. (Method A).

Reference： [1]Patent: WO2011/126567,2011,A1 .Location in patent: Page/Page column 199

47
[ 62140-78-7 ]
[ 637-59-2 ]
[ 1338684-46-0 ]

Yield	Reaction Conditions	Operation in experiment
87%		Preparation of 7-nitro-N-(3-phenylpropyO-2,3-dihydro-l,4-benzodioxin-6- amineTo a 0 C solution of 7-nitro-2,3-dihydro-l ,4-benzodioxin-6-amine (0.500 g, 2.55 mmol) in dry DMF (12 mL, 150 mmol) is added sodium hydride (0.102 g, 2.55 mmol) portion wise (gas evolution). After 15 min, cooling bath is removed and solution stirred 30 min at rt. To this solution is added l-bromo-3-phenylpropane (0.465 mL, 3.06 mmol) dropwise via syringe. After 18 h at rt, the reaction is concentrated in vacuo to remove DMF and the residue is partitioned between DCM and saturated ammonium chloride (50 mL each). The layers are separated, the aqueous is extracted with DCM (3x200mL), and the organics are combined, dried with anhydrous sodium sulfate and concentrated. The residue is subjected to silica gel chromatography (230-400 mesh, 150 g, elution with 5, 10 and 20% EtOAc/hexane) to give 0.695 g (87%) of the desired product as an orange oil. NMR (400 MHz, CDC13) delta 2.05 (2 H, m), 2.77 (2 H, t), 3.22 (2 H, m), 4.22 (2 H, m), 4.33 (2 H, m), 6.19 (1 H, s), 7.22 (3 H, m), 7.31 (2 H, m), 7.74 (1 H, s), 8.02 (1 H, br s); MS (ESI4) for Ci7Hi8N204 m/z 315.1 (M+H)+, HPLC retention time: 4.92 min. (Method A).

Reference： [1]Patent: WO2011/126567,2011,A1 .Location in patent: Page/Page column 201

48
[ 637-59-2 ]
[ 40371-63-9 ]
[ 1338684-19-7 ]

Yield	Reaction Conditions	Operation in experiment
		To a cooled (0-5 C) solution of <strong>[40371-63-9]5-bromo-4-methyl-2-nitroaniline</strong> (0.400 g, 1.73 mmol) in DMF (20 mL) is added sodium hydride (0.077 g, 1.92 mmol). After 5 min., the ice bath is removed and the mixture is stirred at ambient temperature for 30 min. A solution of 1 - bromo-3-phenylpropane (0.290 mL, 1.90 mmol) in DMF (5 mL) is added and the mixture is stirred overnight at rt. Acetic acid (3 mL) is added and the mixture is concentrated. The residue is purified by flash chromatography (230-400 mesh, hexanes/ethyl acetate (0 to 1% containing 0.1% isopropanol) as eluant) to afford 0.540 g (89%) of the desired product as a yellow solid. NMR (CDC13) delta 2.08 (m, 2 H), 2.33 (s, 3 H), 2.80 (t, 2 H), 3.29 (q, 2 H), 7.03 (s, 1 H), 7.27 (m, 5 H), 7.91 (br t, 1 H), 8.03 (s, 1 H).

Reference： [1]Patent: WO2011/126567,2011,A1 .Location in patent: Page/Page column 180

49
[ 637-59-2 ]
[ 7149-80-6 ]
[ 1338684-64-2 ]

Yield	Reaction Conditions	Operation in experiment
95%		Preparation of 5-chloro-4-methyl-2-nitro-N-(3-phenylpropyl)anilineTo a 0-5 C solution of 4-amino-2-chloro-5-nitrotoluene (2.50 g, 0.013 mol) in DMF (60 mL) is added sodium hydride (536 mg, 0.0134 mol) portion wise (gas evolution). After 15 min, the cooling bath is removed and the solution is stirred 30 min. at rt. To this solution is added l-bromo-3-phenylpropane (2.44 mL, 0.016 mol) dropwise via syringe. After 18h at rt, the reaction is concentrated in vacuo and the residue is partitioned between ethyl acetate and saturated aqueous ammonium chloride. The layers are separated and the organic layer is washed with brine, dried (anhydrous sodium sulfate), filtered and concentrated at reduced pressure. The residue is purified by flash chromatography (230- 400 mesh, hexane/ethyl acetate (20%) as eluant) to afford 3.88 g (95 %) of the desired product as an orange oil. NMR (400 MHz, CDC13) delta 2.07 (p, 2 H), 2.29 (s, 3 H), 2.79 (t, 2 H), 3.27 (m, 2 H), 6.81 (s, 1 H), 7.27 (m, 5 H), 7.94 (br t, 1 H), 8.05 (s, 1 H); MS (ESI+) for Ci6H17ClN202 m/z 305.1 (M+H)+, HPLC retention time: 7.88 min. (System A).

Reference： [1]Patent: WO2011/126567,2011,A1 .Location in patent: Page/Page column 212

50
[ 3470-50-6 ]
[ 637-59-2 ]
[ 1305536-44-0 ]

Yield	Reaction Conditions	Operation in experiment
62%	With potassium carbonate; In acetone; for 6h;Reflux;	General procedure: <strong>[3470-50-6]6-Hydroxy-1-tetralone</strong> (0.3 g, 1.85 mmol) was suspended in acetone (15 mL) containing K2CO3 (3.70 mmol). The reaction was treated with an appropriately substituted arylalkyl bromide (2.035 mmol) and heated under reflux for 6 h. The reaction progress was monitored using silica gel TLC with ethyl acetate:petroleum ether (1:2) as mobile phase. Upon completion, the reaction was filtered through a pad of celite and concentrated in vacuo. The crude thus obtained was purified by recrystallization from cyclohexane.
62%	With potassium carbonate; In acetone; for 6h;Reflux;	General procedure: <strong>[3470-50-6]6-Hydroxy-1-tetralone</strong> (0.3 g, 1.85 mmol) was suspended in acetone (15 mL) containing K2CO3 (3.70mmol). The reaction was treated with an appropriately substituted arylalkyl bromide (2.035 mmol) and heated under reflux for 6 h. The reaction progress was monitored using silica gel TLC with ethyl acetate:petroleum ether (1:2) as mobile phase. Upon completion, the reaction was filtered through a pad of celite and concentrated in vacuo. The crude thus obtained was purified by recrystallization from cyclohexane.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 144 - 148
[2]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 2758 - 2763
[3]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 2758 - 2763

51
[ 20603-00-3 ]
[ 637-59-2 ]
[ 144-62-7 ]
[ 1387526-22-8 ]

Yield	Reaction Conditions	Operation in experiment
37%		General procedure: Method 2: To obtain target 3, alcohol 1 (1.25 mL, 9.30 mmol) was reacted with 2 (1 g, 9.30 mmol) in the presence of KOH (2.5 equiv, 1.30 g) in DMF (20 mL/g). The reaction mixture was allowed to stir overnight at room temperature. After completion, the crude reaction mixture was dissolved in H2O and extracted with Et2O. The product was then extracted into 6 M HCl from Et2O. The solution was basified to pH 12-13 with 5 M NaOH (aq) and extract with Et2O. The combined organic layers were washed with brine solution and dried over Na2SO4. After removal of the solvent under reduced pressure, the crude product was purified by column chromatography (silica gel, 5% CHCl3/MeOH/1% NH4OH) followed by formation of oxalate salt from ether.

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 4556 - 4563

52
[ 101-98-4 ]
[ 637-59-2 ]
[ 144-62-7 ]
[ 1387526-30-8 ]

Yield	Reaction Conditions	Operation in experiment
32%		General procedure: Method 2: To obtain target 3, alcohol 1 (1.25 mL, 9.30 mmol) was reacted with 2 (1 g, 9.30 mmol) in the presence of KOH (2.5 equiv, 1.30 g) in DMF (20 mL/g). The reaction mixture was allowed to stir overnight at room temperature. After completion, the crude reaction mixture was dissolved in H2O and extracted with Et2O. The product was then extracted into 6 M HCl from Et2O. The solution was basified to pH 12-13 with 5 M NaOH (aq) and extract with Et2O. The combined organic layers were washed with brine solution and dried over Na2SO4. After removal of the solvent under reduced pressure, the crude product was purified by column chromatography (silica gel, 5% CHCl3/MeOH/1% NH4OH) followed by formation of oxalate salt from ether.

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 4556 - 4563

53
[ 637-59-2 ]
[ 284049-75-8 ]
[ 122-72-5 ]

Reference： [1]Synlett,2012,vol. 23,p. 2692 - 2698,7

54
[ 637-59-2 ]
[ 168824-94-0 ]
[ 1354800-45-5 ]

Yield	Reaction Conditions	Operation in experiment
121 mg		Tert-butyl 1,3,4,9-tetrahydro-2H-beta-carboline-2-carboxylate (CAS No. 168824-94-0) (545 mg) was dissolved in N,N-dimethylformamide (5 mL), (3-bromopropyl)benzene (478 mg), tetrabutylammonium bromide (32 mg) and cesium carbonate (782 mg) were sequentially added and, the mixture was stirred at 60 C. for 4 hours. The reaction mixture was cooled to room temperature, and poured into water, followed by extraction with ethyl acetate. The organic layer was washed sequentially with water and an aqueous saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1). Further, to the resulting compound (162 mg) was added a 4N hydrogen chloride dioxane solution (3 mL) at room temperature, and the mixture was stirred for 1 hour. The reaction mixture was concentrated to obtain the title compound (121 mg) having the following physical property values.; TLC: Rf 0.47 (chloroform:methanol=9:1); 1H-NMR (DMSO-d6): delta 1.84-2.04 (m, 2H), 2.55-2.66 (m, 2H), 2.94 (t, J=5.5 Hz, 2H), 3.41 (t, J=5.5 Hz, 2H), 4.12 (t, J=7.3 Hz, 2H), 4.40 (s, 2H), 7.00-7.10 (m, 1H), 7.10-7.22 (m, 4H), 7.22-7.34 (m, 2H), 7.41 (d, J=8.2 Hz, 1H), 7.47 (d, J=7.7 Hz, 1H), 9.67 (s, 2H).

Reference： [1]Patent: US2013/109699,2013,A1 .Location in patent: Paragraph 0805-0808

55
[ 637-59-2 ]
[ 38427-94-0 ]
[ 1445435-87-9 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 3476 - 3479

56
[ 54197-66-9 ]
[ 637-59-2 ]
[ 1458219-00-5 ]

Yield	Reaction Conditions	Operation in experiment
58%	With potassium hydroxide; In ethanol; for 5h;Reflux;	General procedure: Commercially available 6-hydroxy-3,4-dihydro-2(1H)-quinolinone (6) or 7-hydroxy-3,4-dihydro-2(1H)-quinolinone (7) (1.50 mmol) was suspended in ethanol (6 mL) containing KOH (1.66 mmol). The reaction was treated with an appropriately substituted alkyl bromide (1.50 mmol) and heated at reflux for 5 h. The reaction progress was monitored using silica gel TLC with ethyl acetate as mobile phase. Upon completion, the reaction was poured into aqueous NaOH (1%) and the resulting precipitate was collected by filtration. The crude thus obtained was purified by recrystallization from ethanol.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 5498 - 5502

57
[ 637-59-2 ]
[ 1684-40-8 ]
[ 1440523-97-6 ]

Yield	Reaction Conditions	Operation in experiment
59%		General procedure: Powdered potassium hydroxide (1.27 g, 22.6 mmol) was added to a solution of 7-MEOTA (2.00 g, 7.6 mmol) or THA(2.00 g, 8.5 mmol) in DMSO (30 mL) under nitrogen atmosphere.The mixture was vigorously stirred at room temperaturefor 2 hours. Subsequently, (3-bromopropyl)benzene (15mmol) or (bromomethyl)cyclohexane (15 mmol) was added dropwise and the stirring was continued for further 48 hours at the room temperature under nitrogen atmosphere. The endof reaction was determined with triethylamine-saturated TLC, mobile phase hexane/ethyl-acetate (1:1). When the reaction was finished, water (100 mL) was poured into reaction mixture and the water phase was extracted with ethylacetate(3100 mL). The combined ethyl-acetate extractswere dried over anhydrous sodium sulphate, filtered and the solvent was evaporated under reduced pressure. Evaporation of the solvent gave an oily residue that was purified by triethylamine-pretreated silica gel via column chromatography.The mobile phase hexane/ethyl-acetate (1:1) was usedfor purification. The pure product was isolated as brown crystals [13-16]. N-3-(Phenylpropyl)-1,2,3,4-Tetrahydroacridin-9-Amoniumchloride (1) Yield: 59.0 %; m.p. 195.6 - 196.8 C; 1H NMR spectrum(300 MHz, methanol-d4) delta (ppm): 1.87-1.94 (m, 4H), 2.11-2.20 (m, 2H), 2.54 (t, J = 5.87 Hz, 2H), 2.74 (t, J = 7.34 Hz,2H), 2.97 (t, J = 6.36 Hz, 2H), 3.93 (t, J = 6.85 Hz, 2H),7.12-7.25 (m, 5H), 7.44 (ddd, J = 1.22, 6.85, 8.80 Hz, 1H),7.74 (dd, J = 1.47, 8.56 Hz, 1H), 7.79 (ddd, J = 1.22, 6.84,8.31 Hz, 1H), 8.18 (d, J = 8.80 Hz, 1H); 13C NMR spectrum(75 MHz, methanol-d4) delta (ppm): 21.77, 22.91, 24.76, 29.23,32.81, 33.90, 48.39, 112.74, 116.84, 120.00, 126.17, 126.37,127.18, 129.54, 129.55, 133.97, 139.66, 142.14, 151.44,157.85; ESI-MS: m/z 317.0 [M]+ (calculated for:[C22H25N2]+ 317.2); EA: calculated 74.88 % C, 7.14 % H,7.94 % N; found 74.56 % C, 7.34 % H, 7.85 % N logP =5.49 ± 0.72 (calc. value) [17].

Reference： [1]Letters in Organic Chemistry,2013,vol. 10,p. 291 - 297

58
[ 637-59-2 ]
[ 67469-78-7 ]

Reference： [1]Organic Process Research and Development,2002,vol. 6,p. 621 - 627

59
[ 5788-58-9 ]
[ 637-59-2 ]
[ 1407307-15-6 ]

Yield	Reaction Conditions	Operation in experiment
72%	With tetrabutylammomium bromide; potassium carbonate; In acetonitrile; at 20℃; for 43h;	General procedure: 4,5-Dibromopyridazin-3(2H)-one (28) (7.753g, 30.54mmol, 1.00 equiv), 4-iodobenzyl bromide (70) (12.23g, 41.19mmol, 1.35 equiv), K2CO3 (11.150g, 80.67mmol, 2.64 equiv) and (n-Bu) 4NBr (310 mg, 0.96mmol, 0.03 equiv) were stirred overnight at 20C in CH3CN (100mL), based on published conditions.26 After ?24h the reaction mixture was concentrated to dryness under reduced pressure, and the residue was re-suspended in CH2Cl2, filtered twice through a pad of Celite and the filtrate was concentrated to dryness under reduced pressure. The product was re-precipitated from EtOAc/hexanes, to afford 35 (11.52g, 80%).

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 1029 - 1039

60
[ 921592-91-8 ]
[ 637-59-2 ]
[ 1404063-67-7 ]

Yield	Reaction Conditions	Operation in experiment
70.4%	With potassium carbonate; In acetonitrile; at 85℃; for 12h;	(1) Preparation of 3-methyl-1-(3-phenylpropyl)pyrrolidin-3-ol According to Example 15, <strong>[921592-91-8]3-methylpyrrolidin-3-ol hydrochloride</strong> was synthesized. To a 100 mL reaction flask were added <strong>[921592-91-8]3-methylpyrrolidin-3-ol hydrochloride</strong> (1 g, 7.2 mmol), anhydrous potassium carbonate (2.5 g, 18 mmol) and acetonitrile (15 mL). To the resulting mixture was slowly added a solution of 3-bromopropylbenzene (1.29 g, 6.48 mmol) in acetonitrile dropwisely at 85 C. The reaction was conducted for 12 hours. After the completion of reaction monitored by TLC, the resulting mixture was evaporated under reduced pressure to remove acetonitrile. To the residue was added a mixed solution of dichloromethane and water for extraction. The organic phase was dried over anhydrous sodium sulfate, and evaporated to remove the solvent to produce a crude product. The crude product was purified by column chromatography (silica gel column, eluted with petroleum ether: ethyl acetate=10:1(volumetric ratio)) to produce 3-methyl-1-(3-phenylpropyl)pyrrolidin-3-ol (1 g) in a yield of 70.4%.
70.4%	With potassium carbonate; In acetonitrile; at 85℃; for 12h;	(1) Preparation of 3-methyl-1-(3-phenylpropyl)pyrrolidin-3-ol According to Example 15, <strong>[921592-91-8]3-methylpyrrolidin-3-ol hydrochloride</strong> was synthesized. To a 100mL reaction flask were added <strong>[921592-91-8]3-methylpyrrolidin-3-ol hydrochloride</strong> (1g, 7.2mmol), anhydrous potassium carbonate (2.5g, 18mmol) and acetonitrile (15mL). To the resulting mixture was slowly added a solution of 3-bromopropylbenzene (1.29g, 6.48mmol) in acetonitrile dropwisely at 85C. The reaction was conducted for 12 hours. After the completion of reaction monitored by TLC, the resulting mixture was evaporated under reduced pressure to remove acetonitrile. To the residue was added a mixed solution of dichloromethane and water for extraction. The organic phase was dried over anhydrous sodium sulfate, and evaporated to remove the solvent to produce a crude product. The crude product was purified by column chromatography (silica gel column, eluted with petroleum ether: ethyl acetate = 10:1 (volumetric ratio)) to produce 3-methyl-1-(3-phenylpropyl)pyrrolidin-3-ol (1 g) in a yield of 70.4 %.

Reference： [1]Patent: US2014/45896,2014,A1 .Location in patent: Paragraph 0176; 0177
[2]Patent: EP2703398,2014,A1 .Location in patent: Paragraph 0156; 0157

61
[ 637-59-2 ]
[ 10111-08-7 ]
[ 169378-51-2 ]

Yield	Reaction Conditions	Operation in experiment
69%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere;	General procedure: To a mixture of formylimidazole 1 and K2CO3 in DMF, the required bromide or mesylate was added and the reaction mixture was stirred overnight under atmosphere of nitrogen at rt. The resulting suspension was cooled to room temperature (rt) and filtered. Water was added to the filtrate and the resulting solution was extracted with Et20 (3 x 25 mL). The organic layer was dried over MgS04 and evaporated to give the corresponding alkylimidazole-2- carbaldehyde. -(3-Phenylpropyl)imidazole-2-carbaldehyde oxime (RS2-33C). Prepared according to the general method A using formylimidazole 1 (0.50 g, 5.2 mmol), K2CO3 (0.72 g, 5.2 mmol), and (3-bromopropyl)benzene (1.2 g, 6.2 mmol) in DMF (20 mL). Yellow oil 2b (0.77 g, 69 %).

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 1378 - 1389
[2]Patent: WO2015/57822,2015,A1 .Location in patent: Page/Page column 33; 34

62
[ 637-59-2 ]
[ 68-11-1 ]
[ 30134-08-8 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of 4.0 g sodium hydroxide(100 mmol) in 50 mL methanol 3.47 mL thioglycolic acid (4.61 g, 50 mmol) was addedslowly via a syringe. After stirring at room temperature for 10 min, 7.6 mL 1-bromo-3-phenylpropane (9.96 g, 50 mmol) was added and the mixture was stirred for additional 14 h atroom temperature, then poured on ice and acidified with 10% (w/w) hydrochloric acid to pH4. The aqueous solution was extracted three times with ethyl acetate, the organic layers werecombined and the solvent was evaporated in vacuo, yielding a colorless oil. The crude productwas dissolved in 60 mL glacial acetic acid, 17.2 mL of a 35% (w/w) hydrogen peroxidesolution (6.8 g, 200 mmol) was added and the solution was stirred for additional 14 h. Themixture was poured on ice, the aqueous solution was extracted three times with ethyl acetate,the organic layers were combined, washed with water, the organic phase was separated andthe solvent was evaporated in vacuo to yield a colorless oil, that solidified overnight, yielding7.5 g of red solid (31 mmol, 62%); mp: 80 C; 1H NMR (300 MHz, DMSO-d6) delta = 7.25 (m,5H), 4.27 (s, 2H), 3.27 (m, 2H), 2.71 (t, J = 7.6 Hz, 2H), 2.02 (m, 2H); 13C NMR (75 MHz,DMSO-d6) delta = 164.80, 140.63, 128.49, 128.44, 126.20, 57.41, 52.25, 33.47, 22.96; HR-MS(ESI) m/z calcd for C11H14O4S: 241.05400 (M - H)-, found: 241.05423.

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 4302 - 4312
[2]Bioorganic Chemistry,2020,vol. 94

63
[ 1553-60-2 ]
[ 637-59-2 ]
(±)-2-(4-isobutylphenyl)-5-phenylpentanoic acid [ No CAS ]

Reference： [1]Archiv der Pharmazie,2015,vol. 348,p. 55 - 61

64
[ 5001-96-7 ]
[ 637-59-2 ]
(±)-2-(2-fluorobiphenyl-4-yl)-5-phenylpentanoic acid [ No CAS ]

Reference： [1]Archiv der Pharmazie,2015,vol. 348,p. 55 - 61

65
[ 637-59-2 ]
[ 696-23-1 ]
2-methyl-4-nitro-1-(3-phenylpropyl)-1H-imidazole [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 2103 - 2119

66
[ 344-14-9 ]
[ 637-59-2 ]
C₁₄H₁₇FO₄ [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 972 - 975

67
[ 25981-83-3 ]
[ 637-59-2 ]
C₂₀H₂₃ClN⁽¹⁺⁾*Br^(1-) [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 1228 - 1243

68
[ 25981-83-3 ]
[ 637-59-2 ]
5-chloro-2-((E)-3-((E)-5-chloro-3,3-dimethyl-1-(3-phenylpropyl)-indolin-2-ylidene)prop-1-en-1-yl)-3,3-dimethyl-1-(3-phenylpropyl)-3H-indol-1-ium bromide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 1228 - 1243

69
[ 637-59-2 ]
[ 52427-05-1 ]
1-bromo-4-nitro-2-(3-phenylpropoxy)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To the corresponding bromophenol in ethanol (5 mL/mmol) was added K2CO3 (1.2 eq). The resulted mixture was stirred for 2 h under reflux conditions (90 °C) before the corresponding bromide (1.3 eq) and KI (5molpercent) were added. Reflux was continued overnight. After cooling down, the solvent was removed under reduced pressure and the residue was washed with brine and extracted three times with ethyl acetate. The combined organic layers were dried over Na2SO4, the solvent was removed under reduced pressure and the crude product was purified by flash chromatography on silica gel.

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 96,p. 139 - 150

70
[ 637-59-2 ]
[ 83-30-7 ]
3-phenylpropyl 2,4,6-trihydroxybenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47.1%	With sodium hydrogencarbonate In N,N-dimethyl-formamide at 90℃; for 12h;

Reference： [1]Chen, Dawei; Chen, Ridao; Wang, Ruishan; Li, Jianhua; Xie, Kebo; Bian, Chuancai; Sun, Lili; Zhang, Xiaolin; Liu, Jimei; Yang, Lin; Ye, Fei; Yu, Xiaoming; Dai, Jungui [Angewandte Chemie - International Edition, 2015, vol. 54, # 43, p. 12678 - 12682][Angew. Chem., 2015, vol. 127, # 43, p. 12869 - 12873,5]

71
[ 637-59-2 ]
[ 123770-62-7 ]
ethyl 5-(3-phenylpropoxymethyl)isoxazole-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.9 g		Reference Production Example 105 (0747) 60% Sodium hydride (1.04 g, 26.0 mmol) was added to dehydrated N,N-dimethylformamide (10 ml) cooled to 0C, under a nitrogen atmosphere, and a dehydrated N,N-dimethylformamide (10 ml) solution of <strong>[123770-62-7]ethyl 5-hydroxymethylisoxazole-3-carboxylate</strong> (3.0 g, 17.54 mmol) was added dropwise thereto, and then the mixture was further stirred for 30 minutes. A dehydrated N,N-dimethylformamide (5 ml) solution of 1-bromo-3-phenylpropane (3.5 g, 17.54 mmol) was added thereto, and the mixture was heated to room temperature and stirred for 16 hours. Then, the mixture was added to a saturated aqueous ammonium chloride solution, and extracted twice with ethyl acetate. The organic layer was washed with water and saturated saline water, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was applied to a silica gel column chromatography to obtain 1.9 g of ethyl 5-(3-phenylpropoxymethyl)isoxazole-3-carboxylate represented by the following formula. 1H-NMR (CDCl3, TMS, delta (ppm)) : 7.30-7.25 (m, 2H), 7.20-7.15 (m, 3H), 6.65 (s, 1H), 4.61 (s, 2H), 4.40 (q, 2H), 3.53(t, 2H), 2.70 (t, 2H), 1.98-1.88(m, 2H), 1.42 (t, 3H)

Reference： [1]Patent: EP2952096,2015,A1 .Location in patent: Paragraph 0747

72
[ 4282-77-3 ]
[ 637-59-2 ]
9-[[1-(3-phenylpropyl)-1H-1,2,3-triazol-4-yl]methyl]-9H-carbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%		General procedure: The benzofused N-heteroaromatic alkynes 2, 5, and 8 weresynthesized by reacting benzimidazole (1.0 mmol),benzotriazole (1.0 mmol), or carbazole (1.0 mmol) withpropargyl bromide (1.2 mmol) in the presence of potassiumcarbonate (2.0 mmol) using dimethylformamide bycontinuous stirring at 10-25 C up to 8-10 h [32]. For thesynthesis of target compounds, solution of aromatic bromides(1.0 mmol) in dimethylformamide was taken in around-bottomed flask and aqueous solution of sodium azide(3.0 mmol) was added, thereafter, stirred the reactionmixture for 1 h at 25-40 C. To the above reaction mixture,benzofused N-heteroaromatic alkyne 2 (1.0 mmol), 5(1.0 mmol), or 8 (1.0 mmol) was added followed by coppersulfate pentahydrate (5 mol %) and sodium ascorbate(10 mol %) [33], then, stirred the reaction contents overnight.The progress of reaction was monitored by thin layerchromatography. After the completion of reaction, ice-colddistilled water was added to the reaction mixture andproduct was extracted with ethyl acetate (50 cm3 9 3).The organic layer was washed with aqueous ammoniasolution followed by brine solution and dried using anhydroussodium sulfate. Filtered and evaporated the solventunder vacuum to get crude product which was furtherpurified by column chromatography using hexane:ethylacetate (7:3) as eluent.

Reference： [1]Monatshefte fur Chemie,2016,vol. 147,p. 817 - 828

73
[ 4991-65-5 ]
[ 637-59-2 ]
6-(3-phenylpropoxy)-1,3-benzoxathiol-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
13.4%	With potassium carbonate; In acetone; at 60℃;	General procedure: The 2H-1,3-benzoxathiol-2-one analogues were synthesised according to a literature procedure.1 Commercially available 6-hydroxy-1,3-benzoxathiol-2-one (11; 5 mmol) was dissolved in acetone (10mL). To the reaction was added the appropriate substituted arylalkyl bromide (5 mmol) and anhydrous K2CO3 (12 mmol). The mixture was stirred at 60 C for 5-24 h and monitored with thin-layer chromatography (TLC) until completion. The reaction was filtered to remove the K2CO3 and ethyl acetate(30 mL) was added to the reaction. The resulting solution was washed with deionised H2O (30 mL) and brine (3 × 30 mL), and dried over anhydrous MgSO4. The solvent was removed under reduced pressure and the resulting residue was purified by recrystallisation from ethanol (40 mL).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 1200 - 1204

74
[ 637-59-2 ]
[ 158984-83-9 ]
6-(3-phenylpropoxy)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%		General procedure: Compound 25 (400 mg, 1.60 mmol) was dissolved in DMF, and NaH (60% dispersion in mineral oil, 77 mg, 1.90 mmol) was added at 0 C. After stirring at r.t. for 1 h, 1-bromopropane (233 mg, 1.9 mmol) was added and the reaction mixture was stirred for 1 h. After completion of the reaction, the mixture was diluted with water and extracted with EtOAc and brine. The organic fraction was dried over Na2SO4 and the solvent was evaporated in vacuo. The residue was purified by a flash column chromatography (EtOAc:hexane = 1:5) to afford 26a (381 mg, 82%) as a colorless oil.

Reference： [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 789 - 801

75
[ 637-59-2 ]
[ 114676-59-4 ]
(2R,4R)-methyl 4-hydroxy-1-(3-phenylpropyl)pyrrolidine-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃;Inert atmosphere;	General procedure: To a solution of 19 (1.0 equiv.) and K2CO3 (2.0 equiv.) inanhydrous DMF (2 mL) was added an appropriate alkyl halide (1.0 equiv), and themixture was stirred at room temperature or 80 °C (rt for X = CH2, 80°C for X = CH2CH2; CH2CH2CH2)under N2 atmosphere for appropriate hours. After completion of thereaction (monitored by TLC), the resulting mixture was concentrated in vacuo. The residue was dissolvedin ethyl acetate and washed twice with brine. The organic layer was dried, concentrated in vacuoand the residue was purified by column chromatography on silica gel eluted with DCM/EA (2:1)to give compound 20 as a colorlessoil.(2S,4R)-methyl-1-benzyl-4-hydroxypyrrolidine-2-carboxylate(20a). Yield 88percent.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 2434 - 2437

76
[ 637-59-2 ]
[ 159749-28-7 ]
C₁₇H₂₅NO₂ [ No CAS ]

Reference： [1]Nature,2016,vol. 536,p. 322 - 325

77
[ 873397-34-3 ]
[ 637-59-2 ]
C₁₄H₂₀O [ No CAS ]

Reference： [1]Nature,2016,vol. 536,p. 322 - 325

78
[ 1852-17-1 ]
[ 637-59-2 ]
[ 1219980-35-4 ]
1,3-bis(3-phenylpropyl)tetrahydropyrimidin-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20%; 30%		Tetrahydropyrimidinone (3.30 mmol) was added to the suspension of NaH (3.60 mmol) in cold THF (5 ml), and the mixture was stirred at room temperature for 45 minutes. The reaction mixture was then cooled and then 3-phenylpropyl bromide (3.30 mmol) was added. The reaction mixture was refluxed for a further 5 hours. The reaction was monitored by TLC. Saturated NH4Cl solution was added The excess NaH was neutralized and extracted with ethyl acetate. The crude mixture was purified by column chromatography to give pure title compound.

Reference： [1]Patent: KR2015/111825,2015,A .Location in patent: Paragraph 0613-0616

79
[ 637-59-2 ]
[ 138786-86-4 ]
4-nitro-1-(3-phenylpropyl)-1H-pyrazole-3-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 15h;	General procedure: To a solution of 1 (1.0 g, 5.84 mmol) in DMF (20 mL) were addedK2CO3 (4.04 g, 29.2 mmol) and 1-bromo-2-ethylbutane (891 mL,6.42 mmol). The reaction mixture was heated to 60 C and stirredfor 15 h. The reaction mixturewas diluted with water and extractedwith EtOAc. The organic layer was washed with water and brine,dried over MgSO4, and concentrated in vacuo. The crude productwas purified by silica gel column chromatography (hexane-EtOAc,3:1) to afford 2a as a colorless oil (730 mg, 49%).

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 125,p. 551 - 564

80
[ 1852-17-1 ]
[ 637-59-2 ]
1,3-bis(3-phenylpropyl)tetrahydropyrimidin-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%		Tetrahydropyrimidinone (3.30 mmol) was added to the suspension of NaH (3.60 mmol) in cold THF (5 ml), and the mixture was stirred at room temperature for 45 minutes. The reaction mixture was then cooled and then 3-phenylpropyl bromide (3.30 mmol) was added. The reaction mixture was refluxed for a further 5 hours. The reaction was monitored by TLC. Saturated NH4Cl solution was added to neutralize excess NaH and extracted with ethyl acetate. The crude mixture was purified by column chromatography to give pureOne of the title compounds was obtained

Reference： [1]Patent: KR2016/108281,2016,A .Location in patent: Paragraph 0613-0615

81
[ 915948-92-4 ]
[ 637-59-2 ]
N,N-dimethyl-5-(3-phenylpropyl)pyrimidine-2-carboxamide [ No CAS ]

Reference： [1]Organic Letters,2017,vol. 19,p. 3755 - 3758

82
[ 13472-59-8 ]
[ 637-59-2 ]
2-methoxy-3-(3-phenylpropyl)pyridine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 7085 - 7092

83
[ 356560-80-0 ]
[ 637-59-2 ]
6-(3-phenylpropyl)[1,2,4]triazolo[1,5-a]pyridine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 7085 - 7092

84
[ 637-59-2 ]
[ 117068-71-0 ]
2-(benzyloxy)-6-(3-phenylpropyl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With nickel(II) iodide; pyridine-2-carboxamidine hydrochloride; trifluoroacetic acid; sodium iodide; zinc at 60℃; for 26h; Inert atmosphere;

Reference： [1]Hansen, Eric C.; Li, Changfeng; Yang, Sihang; Pedro, Dylan; Weix, Daniel J. [Journal of Organic Chemistry, 2017, vol. 82, # 14, p. 7085 - 7092]

85
[ 105170-27-2 ]
[ 637-59-2 ]
5-methoxy-2-(3-phenylpropyl)pyridine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 7085 - 7092

86
[ 637-59-2 ]
[ 18502-05-1 ]
C₁₄H₁₅N₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate In N,N-dimethyl-formamide at 20℃;

Reference： [1]Tian, Yinping; Lv, Wenhui; Meng, Qiuyue; Li, Xuewei; Zeng, Wei; Lu, Yaxin; Wang, Peng G.; Jin, Jin; Shen, Jie [Medicinal Chemistry Research, 2017, vol. 26, # 9, p. 2007 - 2014]

87
[ 181950-57-2 ]
[ 637-59-2 ]
4-chloro-7-(3-phenylpropoxy)quinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53.6%		<strong>[181950-57-2]4-chloro-7-hydroxyquinoline</strong> (0.45 g, 2.5 mmol) and DMF (15 ml) were added to a 100 ml round bottom flask and stirred at room temperature for 10 min,Then 60% NaH (0.2 g, 5 mmol) was added, stirred at room temperature for 10 min,A solution of 1-bromo-3-phenylpropane (5 mmol)Continue to react, TLC trace detection.After completion of the reaction, the reaction mixture was poured into water, extracted with ethyl acetate, the organic phase was combined,Pressure concentrated to dry, get a yellow oil, add concentrated hydrochloric acid acidification, a white solid, with 20mL acetone / petroleum ether = 3: 1 heavyCrystallization gave a solid which was then basified to give white crystals (0.03 g, yield 53.6%)
53.6%		4-Chloro-7-hydroxyquinoline (0.45 g, 2.5 mmol) and DMF (15 ml) were added to a 100 ml round-bottom flask at room temperatureAfter stirring for 10 min, 60% NaH (0.2 g, 5 mmol) was added and the mixture was stirred at room temperature for 10 min. 1-Bromo-3-phenylpropane (5 mmol) was added to continue the reaction.The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The combined organic phases were concentrated to dryness under reduced pressure to give a yellow oil which was acidified by adding concentrated hydrochloric acid to give a white solid which was triturated with 20 mL of acetone / petroleum ether = 3: 1 Recrystallization, solidification and alkalization gave white crystals (0.03 g, 53.6% yield).
0.64 g	With sodium hydride; In N,N-dimethyl-formamide; at 20℃;	General procedure: A mixture of <strong>[181950-57-2]4-chloroquinolin-7-ol</strong> 8 (0.72g, 4mmol) and anhydrous DMF (10mL) was stirred at room temperature until clear, and then, 60% NaH (0.4g, 10mmol) and halogenated alkane (20-30mmol) were added. The mixture was stirred at room temperature. After completion of the reaction as indicated by TLC, the solution was poured into H2O (100mL) and extracted with ethyl acetate. The organic phase was made acidic with concentrated hydrochloric acid. Upon removal of solvent, the residue was crystallized from acetone to afford a yellow solid. The solid was dissolved in water and made basic with sodium bicarbonate, and the aqueous mixture was extracted with ethyl acetate. The organic phase was washed with water and brine and then dried over anhydrous sodium sulfate, filtered and evaporated. The resulting oil was purified by column chromatography using a mixture of dichloromethane and methanol 100:1 as the eluent to successfully afford the target products 9a-k in good yield.

Reference： [1]Patent: CN105037266,2017,B .Location in patent: Paragraph 0323-0324; 0345-0346
[2]Patent: CN105017145,2017,B .Location in patent: Paragraph 0327; 0348; 0349
[3]European Journal of Medicinal Chemistry,2019,vol. 162,p. 666 - 678

88
[ 637-59-2 ]
[ 64473-35-4 ]
[ 54877-27-9 ]

Reference： [1]Chemical Science,2017,vol. 8,p. 7009 - 7013

89
[ 23833-97-8 ]
[ 637-59-2 ]
7-chloro-1-(3-phenylpropyl)-4-oxoquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%		General procedure: The 7-substituted-4- (1H) -oxoquinoline (10 mmol) was dissolved in DMF (60 ml) and stirred at room temperature until clear. 60%NaH (0.8 g, 20 mmol). Stir for 5 minutes at room temperature and add the corresponding alkyl halide (15-25 mmol). Stir the reaction at room temperature and check by TLC.After the reaction was completed, the reaction mixture was poured into water and extracted with ethyl acetate (150 ml × 3). The organic phases were combined, washed with water and saturated brine.The organic phase was acidified with concentrated hydrochloric acid (pH 1-2), concentrated to near dryness under reduced pressure, dehydrated in anhydrous ethanol twice, and the residue was recrystallized from acetone.Filtered to give a yellow solid.The yellow solid was dissolved in water, basified with sodium bicarbonate, extracted with ethyl acetate, dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated to dryness under reduced pressure. The residue was recrystallized from ether or ether / petroleum ether to obtain the target product 7a -i. among them

Reference： [1]Patent: CN105017145,2017,B .Location in patent: Paragraph 0176; 0206; 0207; 0222; 0223

90
[ 30483-75-1 ]
[ 637-59-2 ]
C₁₉H₂₃NO [ No CAS ]

Reference： [1]ACS Catalysis,2018,vol. 8,p. 310 - 313

91
[ 101-55-3 ]
[ 637-59-2 ]
1-phenoxy-4-(1-phenylpropyl)benzene [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 1880 - 1883

92
[ 1663-39-4 ]
[ 637-59-2 ]
[ 68716-52-9 ]
tert-butyl (E)-3-(2-(3-phenylpropyl)naphthalen-1-yl)acrylate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 7161 - 7165
Angew. Chem.,2018,vol. 130,p. 7279 - 7283,5

93
[ 39835-11-5 ]
[ 637-59-2 ]
C₂₁H₂₃NO₃ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 7659 - 7663
Angew. Chem.,2018,vol. 130,p. 7785 - 7789,5

94
[ 39835-11-5 ]
[ 637-59-2 ]
4-methoxy-2-(3-phenylpropoxy)benzonitrile [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 7659 - 7663
Angew. Chem.,2018,vol. 130,p. 7785 - 7789,5

95
[ 39755-95-8 ]
[ 637-59-2 ]
5-methoxy-1-(3-phenylpropyl)indolin-2,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With potassium carbonate In dimethyl sulfoxide at 20℃;	3.1.7. Synthesis of N-alkylisatin Derivatives 24, 30 and 31 General procedure: 5-methoxyisatin (1 mmol) or compound 1 [20] were dissolved in DMSO (1.5 mL), then K2CO3(1.5 mmol) and suitable alkyl halide (1 mmol; methyl iodide for 24, 1-bromo-2-phenylethane for30, and 1-bromo-3-phenylpropane for 31) were added at room temperature. After addition of ice,the resulting precipitate was filtered, washed with water and used for subsequently steps withoutfurther purification.

Reference： [1]Purgatorio, Rosa; De Candia, Modesto; De Palma, Annalisa; De Santis, Francesco; Pisani, Leonardo; Campagna, Francesco; Cellamare, Saverio; Altomare, Cosimo Damiano; Catto, Marco [Molecules, 2018, vol. 23, # 7]

96
[ 637-59-2 ]
[ 33529-01-0 ]
1-hexyl-3-(3-phenylpropyl)-1H-imidazol-3-ium bromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	In toluene; at 80℃; for 0.333333h;Microwave irradiation;	General procedure: 1-Hexylimidazole (1 eq) and the appropriate alkyl halide (1 eq) were placed in a closed vessel and exposed to irradiation for 20 min at 80 C using a microwave irradiation. The product was then collected as described in the conventional procedure outlined earlier.

Reference： [1]Molecules,2018,vol. 23

97
[ 637-59-2 ]
[ 1215387-58-8 ]
5-bromo-1-(3-phenylpropyl)-1H-pyrrolo[2,3-c]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To a stirred solution of e-bromo-IH-pyrroloP^-clpyridine (800 mg, 4.06 mmol) in DMF (8 mL), NaH (60%), 243.6 mg, 6.09 mmol) was added at 0C. The reaction mixture was allowed to stir at RT for 45 min, then it was cooled to 0C and methyl iodide (384 mg, 2.706 mmol) was added to the mixture and stirred at RT for 3 h. The reaction mixture was quenched in ice water and extracted with EtOAc (2 x 50 mL), washed with brine (30 mL). The separated organic layer was dried over anhydrous Na2SO4, filtered and the filtrate was concentrated. The resultant crude compound was triturated with n-pentane to afford the title compound (500 mg, 58.6%) as a brown solid. LC-MS (method 1): Rt = 1.26 min; m/z = 210.95 (M+H+).

Reference： [1]Patent: WO2018/149986,2018,A1 .Location in patent: Page/Page column 71; 72

98
[ 7321-55-3 ]
[ 637-59-2 ]
[ 140-29-4 ]
2-phenyl-2-(3-phenylpropyl)malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	Stage #1: phenylacetonitrile With methylmagnesium bromide; lithium chloride In tetrahydrofuran; diethyl ether at 20℃; for 0.5h; Inert atmosphere; Stage #2: 2,2-dimethylmalononitrile In tetrahydrofuran; diethyl ether at 80℃; for 6h; Inert atmosphere; Stage #3: 1-Bromo-3-phenylpropane In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide at 80℃; for 16h; Inert atmosphere;	4.2.3. General procedure A: synthesis of malononitriles fromprimary nitriles using MeMgBr General procedure: Step 1: To an 8-mL culture tube with stir bar was added lithium chloride (1.1 equiv) and the flask was flame-dried under vacuum and cooled under an atmosphere of N2. THF (1.0 M) was added, followed by the appropriate nitrile (1.0 equiv). While stirring, methylmagnesium bromide (1.1 equiv of a solution in Et2O) was added dropwise at r.t., and the solutionwas stirred at r.t. for 30 min under an atmosphere of N2. A 1.1M stock solution of dimethylmanononitrile (DMMN) or dibenzylmalononitrile (DBMN) inTHF was prepared and added at r.t. (1.1 equiv of a 1.1M solution inTHF, reaction volume 0.50M with respect to nitrile starting material). The reaction was stirred at 80 C for 6 h under an atmosphere of N2. Step 2: The reaction was cooled to r.t. and DMF was added to bring the reaction solvent to a 1:1 THF/DMF ratio (0.25Mof a 1:1 THF/DMF mixture with respect to nitrile starting material). The desired electrophile (1.2 equiv) was added in a single portion. Ifthe electrophile was a solid, it was added with the DMF as a 0.60Mstock solution. The reaction was stirred at 80 C for 16 h, or until complete conversion was achieved as judged by TLC. The reaction was cooled to r.t., opened to air, quenched with 1M aq. HCl, and extracted with EtOAc (3). The organic fractions were combined,dried over MgSO4, and concentrated. The crude residue was purified by flash column chromatography to yield the desired malononitrile.

Reference： [1]Mills, L. Reginald; Rousseaux, Sophie A.L. [Tetrahedron, 2019, vol. 75, # 32, p. 4298 - 4306]

99
[ 110-59-8 ]
[ 7321-55-3 ]
[ 637-59-2 ]
2-(3-phenylpropyl)-2-propylmalononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: pentanonitrile With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: 2,2-dimethylmalononitrile In tetrahydrofuran; hexane at 20 - 80℃; for 6h; Inert atmosphere; Stage #3: 1-Bromo-3-phenylpropane In tetrahydrofuran; hexane; N,N-dimethyl-formamide at 80℃; for 16h; Inert atmosphere;	4.2.24. General procedure C Synthesis of malononitriles from alkyl nitriles using LDA: General procedure: Step 1: Toa flame-dried 8-mL culture tube with stir bar was added THF(0.40 mL) and diisopropylamine (67 mL, 0.48 mmol, 1.2 equiv). The solution was cooled to 0 C and n-BuLi (0.28 mL of a 1.6M solutionin hexanes, 0.44 mmol, 1.1 equiv) was added, dropwise, and the reaction was stirred at 0 C for 10 min. The solution was cooledto 78 C and the desired alkyl nitrile was added neat, dropwise (0.40 mmol, 1.0 equiv), and the reaction was stirred at 78 C for1 h. The reaction was warmed to r.t. and a stock solution of dimethylmalononitrile (DMMN) in THF was added (1.1 equiv of a 1.1Msolution in THF; reaction volume 0.50M with respect to alkylnitrile). The reaction was stirred at 80 C for 6 h under an atmosphere of N2. Step 2: The reaction was cooled to r.t. and DMF was added to bring the reaction solvent to a 1:1 THF/DMF ratio (0.25Mof a 1:1 THF/DMF mixture with respect to alkyl nitrile). The desired electrophile (1.2 equiv) was added in a single portion. If the electrophile was a solid, it was added with the DMF as a 0.60M stock solution. The reaction was stirred at 80 C for 16 h, or until complete conversion was achieved as judged by TLC. The reactionwas cooled to r.t., opened to air, quenched with 1M aq. HCl, and extracted withEtOAc (3). The organic fractions were combined, dried over MgSO4, and concentrated. The crude residue was purified by flash column chromatography to yield the desired malononitrile.

Reference： [1]Mills, L. Reginald; Rousseaux, Sophie A.L. [Tetrahedron, 2019, vol. 75, # 32, p. 4298 - 4306]

100
[ 61995-52-6 ]
[ 637-59-2 ]
1-(5-(3-phenylpropyl)-1H-indol-1-yl)ethan-1-one [ No CAS ]

Reference： [1]Organic Process Research and Development,2019,vol. 23,p. 1746 - 1751

101
[ 637-59-2 ]
[ 5326-38-5 ]
2-deutero-3-(3-phenylpropane)-5-nitrotoluene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With potassium dihydrogenphosphate; norbornene; potassium acetate; palladium diacetate; sodium formate; triphenylphosphine; In N,N-dimethyl-formamide; at 50℃; for 16h;Inert atmosphere;	Palladium acetate palladium (44.9 mg, 0.2 mmol) was added to a 25 mL eggplant bottle.Triphenylphosphine (52.4 mg, 0.2 mmol),Sodium formate (276 mg, 4 mmol),Norbornene (188 mg, 2 mmol),Potassium phosphate (2.544 g, 12 mmol), potassium acetate (392 mg, 4 mmol),<strong>[5326-38-5]2-iodo-5-nitrotoluene</strong> (526 mg, 2 mmol),1-Bromo-3-phenylpropane (1.592 g, 8 mmol) and dimethylformamide (10 ml). High purity nitrogen replacement three times,After 16 hours of reaction at 50oC,Extracting the mixture with dichloromethane and water,Combine the organic phase, concentrate the organic solvent,Further purification of the product by column chromatography,2-Chloro-3-(3-phenylpropane)-5-nitrotoluene is obtained,The yield was 71%.

Reference： [1]Patent: CN110054541,2019,A .Location in patent: Paragraph 0022

102
[ 637-59-2 ]
[ 67-20-9 ]
(E)-1-([(5′-nitrofuran-2′-yl)methylene]amino)-3-(3″-phenylpropyl)imidazolidine-2,4-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%		General procedure: <strong>[67-20-9]Nitrofurantoin</strong>, 1, (2.94mmol, 0.7g) was dissolved in 10mL of anhydrous dimethyl formamide (DMF), and trimethylamine (TEA, 4.41mmol, 1.5eq.) was added. The solution was stirred at room temperature for 15min. To resulting yellow solution, the appropriate n-alkyl or benzyl bromide (4.41mmol, 1.5eq) was added. The reaction was stirred at room temperature and monitored by TLC eluting with DCM:MeOH (19:1, v/v). Upon completion, the reaction was quenched with 20mL water and extracted with ethyl acetate (3X20mL). The organic layer was washed once with saturated NH4Cl and once with water. The solution was concentrated in vacuo. The resulting paste was purified by recrystallization in ethanol/water) to afford the desired analogue (Scheme 1 ).

Reference： [1]Bioorganic Chemistry,2020,vol. 96

103
[ 637-59-2 ]
[ 19790-96-6 ]
N-(3-phenylpropyl)-3-(pyridin-4-yl)isoxazol-5-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With caesium carbonate; In N,N-dimethyl-formamide; at 60.0℃; for 16h;	General procedure: To a stirred solution of 3-substituted-isoxazol-5-amine 10 (1.87mmol) in DMF (5mL), Cs2CO3 (1.87mmol) and appropriate bromo compound 11 (1.87mmol) were added at room temperature. The resulting solution was stirred at 60C for 16h. The mixture was cooled, quenched with ice cold water (30mL), and then extracted with EtOAc (2x times). The combined organic extracts were dried over anhydrous Na2SO4 and then concentrated under reduced pressure. The crude mixture was subjected to flash silica gel (230-400 mesh) column chromatography (eluting with 5-10% Ethyl acetate in hexanes) to afford the title compounds 4.

Reference： [1]Bioorganic and Medicinal Chemistry,2020,vol. 28

104
[ 500766-46-1 ]
[ 637-59-2 ]
3-cyclohexyl-N-(3-phenylpropyl)isoxazol-5-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With caesium carbonate In N,N-dimethyl-formamide at 60℃; for 16h;	6.1.1 General procedure for the preparation of compounds 4a-c, 4e-z and 4ab General procedure: To a stirred solution of 3-substituted-isoxazol-5-amine 10 (1.87mmol) in DMF (5mL), Cs2CO3 (1.87mmol) and appropriate bromo compound 11 (1.87mmol) were added at room temperature. The resulting solution was stirred at 60°C for 16h. The mixture was cooled, quenched with ice cold water (30mL), and then extracted with EtOAc (2x times). The combined organic extracts were dried over anhydrous Na2SO4 and then concentrated under reduced pressure. The crude mixture was subjected to flash silica gel (230-400 mesh) column chromatography (eluting with 5-10% Ethyl acetate in hexanes) to afford the title compounds 4.

Reference： [1]Boggu, Pulla Reddy; Venkateswararao, Eeda; Manickam, Manoj; Sharma, Niti; Kang, Jong Seong; Jung, Sang-Hun [Bioorganic and Medicinal Chemistry, 2020, vol. 28, # 22]

105
[ 637-59-2 ]
[ 1611-83-2 ]
(S)-2-methyl-N,6-diphenylhexanamide [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2021,vol. 60,p. 1599 - 1604
Angew. Chem.,2021,vol. 133,p. 1623 - 1628,6

106
[ 637-59-2 ]
[ 183673-70-3 ]
C₂₀H₂₇N₃O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 50℃; for 4h;	The 1-01 (100 mg, 0.37mmol), 3-Phenylpropyl Bromide 15-01 (68.5 mg, 0.37mmol) and K 2CO 3 (105 mg, 0.74mmol) were dissolved in DMF. The reaction mixture was stirred at 50C for 4h. The reaction mixture was diluted by water, and the aqueous layer was extracted by EA for several times. The organic layers was combined, washed with H2O and brine in turn, dried over Na 2SO 4, filtrated and evaporated to give 15-02 as 230 mg colorless crystal as crude product, which was used without further purification. Mass (m/z) : 374.22 [M+H] +.

Reference： [1]Patent: WO2021/78132,2021,A1 .Location in patent: Paragraph 088

107
[ 16096-32-5 ]
[ 637-59-2 ]
4-methyl-3-((3-phenylpropyl)selanyl)-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With selenium; sodium t-butanolate In acetonitrile at 40℃; for 6h; Sealed tube;	3.1. 0.3 mmol scale General procedure: To a 8.0-mL scintillation vial equipped with a magnetic stirrer, indole 1a (0.36 mmol, 1.2 equiv.), selenium powder 2 (0.36 mmol, 1.2 equiv.), t-BuONa (0.45 mmol, 1.5 equiv.), solvent CH3CN (1.0 mL) and (3-bromopropyl)benzene 3a (0.30 mmol, 1.0 equiv.) sequentially added at room temperature. The vial was sealed with a screw-top septum cap and placed in a heating block that was preheated to 40 °C for 6h. After the indicated reaction time, an aqueous saturated NH4Cl solution and EtOAc were added and the layers were separated. The aqueous phase was extracted with EtOAc (x 3) and the combined organic layers were dried over Na2SO4 and concentrated. The residue was purified by flash column chromatography on silica gel (eluent: Petroleum ether/EtOAc) to give the target product 4aa as a Colorless oil.

Reference： [1]Cai, Zhong-Jian; Ji, Shun-Jun; Liu, Huan [Chinese Chemical Letters, 2022]

108
[ 3420-02-8 ]
[ 637-59-2 ]
6-methyl-3-((3-phenylpropyl)selanyl)-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With selenium; sodium t-butanolate In acetonitrile at 40℃; for 6h; Sealed tube;	3.1. 0.3 mmol scale General procedure: To a 8.0-mL scintillation vial equipped with a magnetic stirrer, indole 1a (0.36 mmol, 1.2 equiv.), selenium powder 2 (0.36 mmol, 1.2 equiv.), t-BuONa (0.45 mmol, 1.5 equiv.), solvent CH3CN (1.0 mL) and (3-bromopropyl)benzene 3a (0.30 mmol, 1.0 equiv.) sequentially added at room temperature. The vial was sealed with a screw-top septum cap and placed in a heating block that was preheated to 40 °C for 6h. After the indicated reaction time, an aqueous saturated NH4Cl solution and EtOAc were added and the layers were separated. The aqueous phase was extracted with EtOAc (x 3) and the combined organic layers were dried over Na2SO4 and concentrated. The residue was purified by flash column chromatography on silica gel (eluent: Petroleum ether/EtOAc) to give the target product 4aa as a Colorless oil.

Reference： [1]Cai, Zhong-Jian; Ji, Shun-Jun; Liu, Huan [Chinese Chemical Letters, 2022]

109
[ 905966-40-7 ]
[ 637-59-2 ]
methyl 4-(3-phenylpropyl)benzoate [ No CAS ]

Reference： [1]ACS Catalysis,2022,vol. 12,p. 1905 - 1918

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Technical Information

• Acid-Catalyzed α -Halogenation of Ketones • Addition of a Hydrogen Halide to an Internal Alkyne • Alcohols from Haloalkanes by Acetate Substitution-Hydrolysis • Alcohols React with PX3 • Alkyl Halide Occurrence • Alkylation of an Alkynyl Anion • An Alkane are Prepared from an Haloalkane • Benzylic Oxidation • Birch Reduction • Birch Reduction of Benzene • Blanc Chloromethylation • Complete Benzylic Oxidations of Alkyl Chains • Complete Benzylic Oxidations of Alkyl Chains • Conversion of Amino with Nitro • Convert Haloalkanes into Alcohols by SN2 • Deprotonation of Methylbenzene • Directing Electron-Donating Effects of Alkyl • Electrophilic Chloromethylation of Polystyrene • Friedel-Crafts Alkylation of Benzene with Acyl Chlorides • Friedel-Crafts Alkylation of Benzene with Carboxylic Anhydrides • Friedel-Crafts Alkylation of Benzene with Haloalkanes • Friedel-Crafts Alkylation Using Alkenes • Friedel-Crafts Alkylations of Benzene Using Alkenes • Friedel-Crafts Alkylations Using Alcohols • Friedel-Crafts Reaction • General Reactivity • Grignard Reaction • Groups that Withdraw Electrons Inductively Are Deactivating and Meta Directing • Halogenation of Alkenes • Halogenation of Benzene • Hiyama Cross-Coupling Reaction • Hydrogenation to Cyclohexane • Hydrogenolysis of Benzyl Ether • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Methylation of Ammonia • Methylation of Ammonia • Nitration of Benzene • Nucleophilic Aromatic Substitution • Nucleophilic Aromatic Substitution with Amine • Oxidation of Alkyl-substituted Benzenes Gives Aromatic Ketones • Preparation of Alkylbenzene • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Dihalides • Reductive Removal of a Diazonium Group • Reverse Sulfonation——Hydrolysis • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Sulfonation of Benzene • Suzuki Coupling • The Acylium Ion Attack Benzene to Form Phenyl Ketones • The Claisen Rearrangement • The Nitro Group Conver to the Amino Function • Vilsmeier-Haack Reaction • Williamson Ether Syntheses

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P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 637-59-2 ] {[proInfo.proName]}

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[ 637-59-2 ] Synthesis Path-Upstream 1~8

[ 637-59-2 ] Synthesis Path-Downstream 1~109

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Aryls

Bromides

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[ 637-59-2 ]