[ CAS No. 26478-16-0 ] {[proInfo.proName]}

Name: 26478-16-0|2-(2-Bromoethyl)thiophene|95%
Brand: Ambeed
SKU: A712726
Rating: 96 (35 reviews)

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

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Quality Control of [ 26478-16-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 26478-16-0 ]

Product Details of [ 26478-16-0 ]

CAS No. :	26478-16-0	MDL No. :	MFCD12031720
Formula :	C₆H₇BrS	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JSELWWIIPRBECO-UHFFFAOYSA-N
M.W :	191.09	Pubchem ID :	566160
Synonyms :

Calculated chemistry of [ 26478-16-0 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.33
Num. rotatable bonds :	2
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	41.96
TPSA :	28.24 Å²

Pharmacokinetics

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

Lipophilicity

Log Po/w (iLOGP) :	2.28
Log Po/w (XLOGP3) :	2.71
Log Po/w (WLOGP) :	2.69
Log Po/w (MLOGP) :	2.43
Log Po/w (SILICOS-IT) :	3.83
Consensus Log Po/w :	2.79

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.06
Solubility :	0.165 mg/ml ; 0.000866 mol/l
Class :	Soluble
Log S (Ali) :	-2.96
Solubility :	0.211 mg/ml ; 0.00111 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.33
Solubility :	0.0894 mg/ml ; 0.000468 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.28

Safety of [ 26478-16-0 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P301+P330+P331-P303+P361+P353-P363-P304+P340-P310-P321-P260-P264-P280-P305+P351+P338-P405-P501	UN#:	3265
Hazard Statements:	H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 26478-16-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 26478-16-0 ]

[ 26478-16-0 ] Synthesis Path-Downstream 1~87

1
[ 5402-55-1 ]
[ 26478-16-0 ]

Yield	Reaction Conditions	Operation in experiment
94%	With carbon tetrabromide; triphenylphosphine In tetrahydrofuran at 0℃; Schlenk technique; Inert atmosphere;
69%	With bromine; triphenylphosphine In dichloromethane at 20℃;
64%		P.31 Synthesis of 2-(2-bromoethyl)thiophene Production Example 31 Synthesis of 2-(2-bromoethyl)thiophene 2-Thienylethanol (0.44 ml) was treated as in the above Production Example 1 to give the title compound (0.490 g) as a colorless oil (yield: 64.0%). 1H-NMR (400 MHz, CDCl3): δ(ppm) 3.38(2H, t, J=7.6Hz), 3.58(2H, t, J=7.6Hz), 6.89(1H, d, J=1.2Hz), 6.96(1H, d, J=4.2Hz), 7.19(1H, dd, J=1.2, 4.2Hz).

28%	With phosphorus tribromide In dichloromethane at 0 - 20℃; for 1h;
19%	With phosphorus tribromide In tetrachloromethane at 65℃; for 0.333333h;	a Phosphorus tribromide (2.0 mL, 21.1 mmol) was added to a stirred solution of 2-(thiophen-2-yl)ethanol (2.25 g, 17.6 mmol) in carbon tetrachloride (162 mL) then the mixture heated at 65° C. for 20 minutes. The mixture was allowed to cool to ambient temperature then ice added. The organic layer was separated then the aqueous layer extracted with dichloromethane (2×30 mL). The combined organic layers were washed with brine, then dried (NaSO4), filtered and reduced in vacuo. The residue was purified by flash chromatography over silica, eluting with ethyl acetate:hexane mixtures 0:100 to 0.5:95.5 to give 2-(2-bromoethyl)thiophene as a brown oil (650 mg, 19%).
	With pyridine; chloroform; phosphorus tribromide
	With phosphorus tribromide In diethyl ether at 0℃; for 4h;	2D Example 2D; 9-(4,5-Dimethyl-thiazol-2-yl)-4-[4-(2-thiophen-2-yl-ethyl)-piperazin-1-yl]-5,6,7, 8- TETRAHYDRO-1, 3, 4B-TRIAZA-FLUORENE To a solution of 2-(2-thienyl) ethanol (1.63g) in dry ether (15mL) at 0°C was added PBr3 (1. 31mL) dropwise. After 4 hours the reaction mixture was diluted with dichloromethane, washed with water, dried (MGS04) and the solvent removed in vacuo to yield a brown oil which was purified using flash chromatography to yield 2- (2-bromo-ethyl)-thiophene. A mixture of 9- (4, 5-DIMETHYL-THIAZOL-2-YL)-4-PIPERAZIN-1-YL-5, 6,7, 8-TETRAHYDRO- 1, 3, 4b-triaza-fluorene (85mg), 2- (2-bromo-ethyl)-thiophene (44mg) and potassium carbonate (38mg) was heated to reflux in acetonitrile (5ML) for 4 hours. The reaction mixture was cooled, extracted into dichloromethane, dried (MGS04) and the solvent removed in vacuo to yield crude product which was purified using flash chromatography to yield the title compound (30mg).

Reference： [1]Li, Lixin; Zhao, Zhengguang; Xu, Jing; Luo, Haotian; Li, Yong; Ma, Xiantao; Tang, Lin; Ren, Bo; Cao, Xinhua; Ma, Yan-Na [Chemical Communications, 2020, vol. 56, # 65, p. 9384 - 9387]
[2]Martins, Andrew; Lautens, Mark [Journal of Organic Chemistry, 2008, vol. 73, # 22, p. 8705 - 8710]
[3]Current Patent Assignee: EISAI CO LTD - US2002/19531, 2002, A1
[4]Meiers, Joscha; Zahorska, Eva; Röhrig, Teresa; Hauck, Dirk; Wagner, Stefanie; Titz, Alexander [Journal of Medicinal Chemistry, 2020, vol. 63, # 20, p. 11707 - 11724]
[5]Current Patent Assignee: AMURA HOLDINGS LIMITED - US2009/131502, 2009, A1 Location in patent: Page/Page column 26-27
[6]Cagniant et al. [Bulletin de la Societe Chimique de France, 1948, p. 1083,1085] Blicke; Burckhalter [Journal of the American Chemical Society, 1942, vol. 64, p. 477,479]
[7]Current Patent Assignee: XENOVA GMBH - WO2004/65389, 2004, A1 Location in patent: Page 47

2
[ 26478-16-0 ]
[ 105-53-3 ]
[ 174312-77-7 ]

Yield	Reaction Conditions	Operation in experiment
30%	Stage #1: diethyl malonate With sodium hydride In tetrahydrofuran at 0 - 20℃; for 1h; Schlenk technique; Inert atmosphere; Stage #2: 2-(2-Bromoethyl)thiophene In tetrahydrofuran at 70℃; Schlenk technique; Inert atmosphere;
	With ethanol; sodium ethanolate
	Stage #1: diethyl malonate With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 1h; Stage #2: 2-(2-Bromoethyl)thiophene at 0 - 20℃; for 12h;

Reference： [1]Li, Lixin; Zhao, Zhengguang; Xu, Jing; Luo, Haotian; Li, Yong; Ma, Xiantao; Tang, Lin; Ren, Bo; Cao, Xinhua; Ma, Yan-Na [Chemical Communications, 2020, vol. 56, # 65, p. 9384 - 9387]
[2]Cagniant [Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1948, vol. 226, p. 1376]
[3]Dong, Kaiwu; Ren, Xinyi; Shen, Chaoren; Wang, Guangzhu [Chemical Communications, 2022, vol. 58, # 8, p. 1135 - 1138]

3
[ 26478-16-0 ]
[ 30433-91-1 ]

Yield	Reaction Conditions	Operation in experiment
	With ethanol; ammonia

Reference： [1]Blicke; Burckhalter [Journal of the American Chemical Society, 1942, vol. 64, p. 477,479]

4
[ 26478-16-0 ]
[ 106891-32-1 ]

Yield	Reaction Conditions	Operation in experiment
	With ethanol; methylamine

Reference： [1]Blicke; Burckhalter [Journal of the American Chemical Society, 1942, vol. 64, p. 477,479]

5
[ 26478-16-0 ]
[ 3289-28-9 ]
[ 78645-47-3 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; diisopropylamine 1.) THF, hexane, -10 deg C, 2.) r.t., 2 h; Yield given. Multistep reaction;

Reference： [1]Stanetty, Peter [Journal of Chemical Research, Miniprint, 1981, # 5, p. 1784 - 1797]

6
[ 26478-16-0 ]
[ 94-09-7 ]
[ 61440-50-4 ]

Yield	Reaction Conditions	Operation in experiment
24%	In N,N,N,N,N,N-hexamethylphosphoric triamide at 125℃; for 24h;

Reference： [1]Albright; DeVries; Largis; Miner; Reich; Schaffer; Shepherd; Upeslacis [Journal of Medicinal Chemistry, 1983, vol. 26, # 10, p. 1378 - 1393]

7
[ 26478-16-0 ]
[ 120022-21-1 ]
Acetic acid 4-(acetyl-phenyl-amino)-1-(2-thiophen-2-yl-ethyl)-piperidin-4-ylmethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With potassium carbonate; potassium iodide In acetonitrile for 18h; Heating;

Reference： [1]Colapret; Diamantidis; Spencer; Spaulding; Rudo [Journal of Medicinal Chemistry, 1989, vol. 32, # 5, p. 968 - 974]

8
[ 26478-16-0 ]
Acetic acid 4-(phenyl-propionyl-amino)-piperidin-4-ylmethyl ester [ No CAS ]
Acetic acid 4-(phenyl-propionyl-amino)-1-(2-thiophen-2-yl-ethyl)-piperidin-4-ylmethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34%	With potassium carbonate; potassium iodide In acetonitrile Heating;

Reference： [1]Colapret; Diamantidis; Spencer; Spaulding; Rudo [Journal of Medicinal Chemistry, 1989, vol. 32, # 5, p. 968 - 974]

9
[ 26478-16-0 ]
Propionic acid 4-(phenyl-propionyl-amino)-piperidin-4-ylmethyl ester [ No CAS ]
Propionic acid 4-(phenyl-propionyl-amino)-1-(2-thiophen-2-yl-ethyl)-piperidin-4-ylmethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With potassium carbonate; potassium iodide In acetonitrile for 18h; Heating;

Reference： [1]Colapret; Diamantidis; Spencer; Spaulding; Rudo [Journal of Medicinal Chemistry, 1989, vol. 32, # 5, p. 968 - 974]

10
[ 26478-16-0 ]
Carbonic acid methyl ester 4-(phenyl-propionyl-amino)-piperidin-4-ylmethyl ester [ No CAS ]
Carbonic acid methyl ester 4-(phenyl-propionyl-amino)-1-(2-thiophen-2-yl-ethyl)-piperidin-4-ylmethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34%	With potassium carbonate; potassium iodide In acetonitrile Heating;

Reference： [1]Colapret; Diamantidis; Spencer; Spaulding; Rudo [Journal of Medicinal Chemistry, 1989, vol. 32, # 5, p. 968 - 974]

11
[ 26478-16-0 ]
Carbonic acid ethyl ester 4-(phenyl-propionyl-amino)-piperidin-4-ylmethyl ester [ No CAS ]
N-(2-Thien-2-ylethyl)-4-[(N-carbethoxyoxy)methyl]-4-(N-propionanilido)piperidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With potassium carbonate; potassium iodide In acetonitrile Heating;

Reference： [1]Colapret; Diamantidis; Spencer; Spaulding; Rudo [Journal of Medicinal Chemistry, 1989, vol. 32, # 5, p. 968 - 974]

12
[ 26478-16-0 ]
Butyric acid 4-(butyryl-phenyl-amino)-piperidin-4-ylmethyl ester [ No CAS ]
Butyric acid 4-(butyryl-phenyl-amino)-1-(2-thiophen-2-yl-ethyl)-piperidin-4-ylmethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With potassium carbonate; potassium iodide In acetonitrile for 18h; Heating;

Reference： [1]Colapret; Diamantidis; Spencer; Spaulding; Rudo [Journal of Medicinal Chemistry, 1989, vol. 32, # 5, p. 968 - 974]

13
[ 26478-16-0 ]
2,2-Dimethyl-propionic acid 4-(phenyl-propionyl-amino)-piperidin-4-ylmethyl ester [ No CAS ]
2,2-Dimethyl-propionic acid 4-(phenyl-propionyl-amino)-1-(2-thiophen-2-yl-ethyl)-piperidin-4-ylmethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39%	With potassium carbonate; potassium iodide In acetonitrile Heating;

Reference： [1]Colapret; Diamantidis; Spencer; Spaulding; Rudo [Journal of Medicinal Chemistry, 1989, vol. 32, # 5, p. 968 - 974]

14
[ 26478-16-0 ]
Isobutyric acid 4-(isobutyryl-phenyl-amino)-piperidin-4-ylmethyl ester [ No CAS ]
Isobutyric acid 4-(isobutyryl-phenyl-amino)-1-(2-thiophen-2-yl-ethyl)-piperidin-4-ylmethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With potassium carbonate; potassium iodide In acetonitrile for 18h; Heating;

Reference： [1]Colapret; Diamantidis; Spencer; Spaulding; Rudo [Journal of Medicinal Chemistry, 1989, vol. 32, # 5, p. 968 - 974]

15
[ 26478-16-0 ]
2-Methoxy-propionic acid 4-[(2-methoxy-propionyl)-phenyl-amino]-piperidin-4-ylmethyl ester [ No CAS ]
2-Methoxy-propionic acid 4-[(2-methoxy-propionyl)-phenyl-amino]-1-(2-thiophen-2-yl-ethyl)-piperidin-4-ylmethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%	With potassium carbonate; potassium iodide In acetonitrile for 18h; Heating;

Reference： [1]Colapret; Diamantidis; Spencer; Spaulding; Rudo [Journal of Medicinal Chemistry, 1989, vol. 32, # 5, p. 968 - 974]

16
[ 26478-16-0 ]
Benzoic acid 4-(benzoyl-phenyl-amino)-piperidin-4-ylmethyl ester [ No CAS ]
Benzoic acid 4-(benzoyl-phenyl-amino)-1-(2-thiophen-2-yl-ethyl)-piperidin-4-ylmethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium carbonate; potassium iodide In acetonitrile for 18h; Heating;

Reference： [1]Colapret; Diamantidis; Spencer; Spaulding; Rudo [Journal of Medicinal Chemistry, 1989, vol. 32, # 5, p. 968 - 974]

17
[ 26478-16-0 ]
[ 62952-33-4 ]
[ 197094-80-7 ]

Yield	Reaction Conditions	Operation in experiment
78%	With lithium diisopropyl amide In tetrahydrofuran for 18h; Heating;

Reference： [1]Liu, Hsing-Jang; Tran, Duong Duc-Phi [Tetrahedron Letters, 1997, vol. 38, # 37, p. 6501 - 6504]

Yield	Reaction Conditions	Operation in experiment
	Rk. mit Verb. XXI;
	Rk. mit EtONa/EtOH;
	der Rk. mit EtONa/EtOH (Tab. 1);

20
[ 26478-16-0 ]
[ 5722-13-4 ]

Yield	Reaction Conditions	Operation in experiment
	With ethanol; water

Reference： [1]Cagniant et al. [Bulletin de la Societe Chimique de France, 1948, p. 1083,1085]

21
[ 26478-16-0 ]
[ 609-08-5 ]
[ 19995-39-2 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: Diethyl methylmalonate With sodium In ethanol for 0.0833333h; Heating; Stage #2: 2-(2-Bromoethyl)thiophene In ethanol for 5h; Heating; Further stages.;

Reference： [1]Nordin, Ove; Nguyen, Ba-Vu; Voerde, Carin; Hedenstroem, Erik; Hoegberg, Hans-Erik [Journal of the Chemical Society. Perkin Transactions 1 (2001), 2000, # 3, p. 367 - 376]

22
[ 26478-16-0 ]
[ 16196-82-0 ]
[ 852050-12-5 ]

Yield	Reaction Conditions	Operation in experiment
75%	Stage #1: 2-(2-Bromoethyl)thiophene With magnesium In diethyl ether Stage #2: 7-acetyl-6,14-endo-ethano-6,7,8,14-tetrahydrothebaine In diethyl ether; benzene for 3h; Heating;

Reference： [1]Liu, Chun-He; Liu, He; Han, Xiang-Yu; Wu, Bo; Zhong, Bo-Hua; Gong, Ze-Hui [Synthetic Communications, 2005, vol. 35, # 5, p. 701 - 710]

23
[ 26478-16-0 ]
[ 16196-82-0 ]
[ 503186-22-9 ]
[ 852050-12-5 ]

Yield	Reaction Conditions	Operation in experiment
1: 75% 2: 8%	Stage #1: 2-(2-Bromoethyl)thiophene With magnesium In diethyl ether Stage #2: 7-acetyl-6,14-endo-ethano-6,7,8,14-tetrahydrothebaine In diethyl ether; benzene for 3h; Heating;

Reference： [1]Liu, He; Wang, Jingyan; Zhong, Bohua [Collection of Czechoslovak Chemical Communications, 2005, vol. 70, # 2, p. 237 - 246]

24
[ 30433-91-1 ]
[ 26478-16-0 ]
[ 923284-00-8 ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium carbonate In acetonitrile for 64h; Heating;

Reference： [1]Baier, Martin; Gleiter, Rolf; Rominger, Frank [European Journal of Organic Chemistry, 2006, # 23, p. 5264 - 5278]

25
[ 26478-16-0 ]
[ 73918-57-7 ]
[ 923284-26-8 ]

Yield	Reaction Conditions	Operation in experiment
89.4%	With potassium carbonate In acetonitrile for 72h; Heating;

Reference： [1]Baier, Martin; Gleiter, Rolf; Rominger, Frank [European Journal of Organic Chemistry, 2006, # 23, p. 5264 - 5278]

26
[ 26478-16-0 ]
[ 64-04-0 ]
[ 923283-98-1 ]

Yield	Reaction Conditions	Operation in experiment
62%	With potassium carbonate In acetonitrile for 72h; Heating;

Reference： [1]Baier, Martin; Gleiter, Rolf; Rominger, Frank [European Journal of Organic Chemistry, 2006, # 23, p. 5264 - 5278]

27
[ 26478-16-0 ]
[ 75-77-4 ]
[ 788130-27-8 ]
C₁₅H₂₄OSSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-(2-Bromoethyl)thiophene With magnesium In tetrahydrofuran for 2.5h; Stage #2: With copper(l) iodide In tetrahydrofuran at 0℃; for 0.0833333h; Stage #3: chloro-trimethyl-silane; 3-methyl-cyclopentadienone With N,N,N,N,-tetramethylethylenediamine; triethylamine In tetrahydrofuran at -78 - 20℃; for 5h; Further stages.;

Reference： [1]Sperry, Jeffrey B.; Ghiviriga, Ion; Wright, Dennis L. [Chemical Communications, 2006, # 2, p. 194 - 196]

28
[ 26478-16-0 ]
[ 851758-72-0 ]
C₂₅H₂₇N₇O₂S₂ [ No CAS ]

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

Reference： [1]Bendale, Pravin; Olepu, Srinivas; Suryadevara, Praveen Kumar; Bulbule, Vivek; Rivas, Kasey; Nallan, Laxman; Smart, Brian; Yokoyama, Kohei; Ankala, Sudha; Pendyala, Prakash Rao; Floyd, David; Lombardo, Louis J.; Williams, David K.; Buckner, Frederick S.; Chakrabarti, Debopam; Verlinde, Christophe L. M. J.; Van Voorhis, Wesley C.; Gelb, Michael H. [Journal of Medicinal Chemistry, 2007, vol. 50, # 19, p. 4585 - 4605]

29
[ 26478-16-0 ]
[ 923284-33-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 89.4 percent / K₂CO₃ / acetonitrile / 72 h / Heating 2: 98 percent / copper(I)iodide; Et₂N / tetrakis(triphenylphosphane)palladium⁽⁰⁾ / tetrahydrofuran / 1 h / 45 °C 3: 66.5 percent / KOH / methanol; tetrahydrofuran; H₂O / 2 h / 20 °C

Reference： [1]Baier, Martin; Gleiter, Rolf; Rominger, Frank [European Journal of Organic Chemistry, 2006, # 23, p. 5264 - 5278]

30
[ 26478-16-0 ]
[ 923284-16-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 62 percent / K₂CO₃ / acetonitrile / 72 h / Heating 2.1: nBuLi / tetrahydrofuran / 0 - 20 °C 2.2: 87 percent / iodine / tetrahydrofuran / -78 - 20 °C

Reference： [1]Baier, Martin; Gleiter, Rolf; Rominger, Frank [European Journal of Organic Chemistry, 2006, # 23, p. 5264 - 5278]

31
[ 26478-16-0 ]
[ 923284-24-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: 62 percent / K₂CO₃ / acetonitrile / 72 h / Heating 2.1: nBuLi / tetrahydrofuran / 0 - 20 °C 2.2: 87 percent / iodine / tetrahydrofuran / -78 - 20 °C 3.1: 99 percent / copper(I)iodide; Et₂N / tetrakis(triphenylphosphane)palladium⁽⁰⁾ / tetrahydrofuran / 1 h / 45 °C 4.1: 95 percent / NaOH / tetrahydrofuran; H₂O / 2 h

Reference： [1]Baier, Martin; Gleiter, Rolf; Rominger, Frank [European Journal of Organic Chemistry, 2006, # 23, p. 5264 - 5278]

32
[ 26478-16-0 ]
[ 923284-30-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 89.4 percent / K₂CO₃ / acetonitrile / 72 h / Heating 2: 98 percent / copper(I)iodide; Et₂N / tetrakis(triphenylphosphane)palladium⁽⁰⁾ / tetrahydrofuran / 1 h / 45 °C

Reference： [1]Baier, Martin; Gleiter, Rolf; Rominger, Frank [European Journal of Organic Chemistry, 2006, # 23, p. 5264 - 5278]

33
[ 26478-16-0 ]
[ 923284-17-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 80 percent / K₂CO₃ / acetonitrile / 64 h / Heating 2.1: n-BuLi / tetrahydrofuran / 0 - 20 °C 2.2: 61 percent / iodine / tetrahydrofuran / -78 - 20 °C

Reference： [1]Baier, Martin; Gleiter, Rolf; Rominger, Frank [European Journal of Organic Chemistry, 2006, # 23, p. 5264 - 5278]

34
[ 26478-16-0 ]
[ 923284-25-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: 80 percent / K₂CO₃ / acetonitrile / 64 h / Heating 2.1: n-BuLi / tetrahydrofuran / 0 - 20 °C 2.2: 61 percent / iodine / tetrahydrofuran / -78 - 20 °C 3.1: 99 percent / copper(I)iodide; Et₂N / tetrakis(triphenylphosphane)palladium⁽⁰⁾ / tetrahydrofuran / 1 h / 45 °C 4.1: 99 percent / NaOH / tetrahydrofuran; H₂O / 2 h

Reference： [1]Baier, Martin; Gleiter, Rolf; Rominger, Frank [European Journal of Organic Chemistry, 2006, # 23, p. 5264 - 5278]

35
[ 26478-16-0 ]
[ 923284-19-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: 62 percent / K₂CO₃ / acetonitrile / 72 h / Heating 2.1: nBuLi / tetrahydrofuran / 0 - 20 °C 2.2: 87 percent / iodine / tetrahydrofuran / -78 - 20 °C 3.1: 99 percent / copper(I)iodide; Et₂N / tetrakis(triphenylphosphane)palladium⁽⁰⁾ / tetrahydrofuran / 1 h / 45 °C

Reference： [1]Baier, Martin; Gleiter, Rolf; Rominger, Frank [European Journal of Organic Chemistry, 2006, # 23, p. 5264 - 5278]

36
[ 26478-16-0 ]
[ 923284-21-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: 80 percent / K₂CO₃ / acetonitrile / 64 h / Heating 2.1: n-BuLi / tetrahydrofuran / 0 - 20 °C 2.2: 61 percent / iodine / tetrahydrofuran / -78 - 20 °C 3.1: 99 percent / copper(I)iodide; Et₂N / tetrakis(triphenylphosphane)palladium⁽⁰⁾ / tetrahydrofuran / 1 h / 45 °C

Reference： [1]Baier, Martin; Gleiter, Rolf; Rominger, Frank [European Journal of Organic Chemistry, 2006, # 23, p. 5264 - 5278]

37
[ 26478-16-0 ]
1,4-bis[4-(2-{bis[2-(2-thienyl)ethyl]amino}ethyl)phentl]buta-1,3-diyne [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 89.4 percent / K₂CO₃ / acetonitrile / 72 h / Heating 2: 98 percent / copper(I)iodide; Et₂N / tetrakis(triphenylphosphane)palladium⁽⁰⁾ / tetrahydrofuran / 1 h / 45 °C 3: 66.5 percent / KOH / methanol; tetrahydrofuran; H₂O / 2 h / 20 °C 4: 95.3 percent / CuCl; pyridine; air / 2 h

Reference： [1]Baier, Martin; Gleiter, Rolf; Rominger, Frank [European Journal of Organic Chemistry, 2006, # 23, p. 5264 - 5278]

38
[ 26478-16-0 ]
1,12-bis(2-phenylethyl)-1,12-diaza-4,9,15,20(2,5)-tetrathiophenacyclodocosaphane-5,7,16,18-tetrayne [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: 62 percent / K₂CO₃ / acetonitrile / 72 h / Heating 2.1: nBuLi / tetrahydrofuran / 0 - 20 °C 2.2: 87 percent / iodine / tetrahydrofuran / -78 - 20 °C 3.1: 99 percent / copper(I)iodide; Et₂N / tetrakis(triphenylphosphane)palladium⁽⁰⁾ / tetrahydrofuran / 1 h / 45 °C 4.1: 95 percent / NaOH / tetrahydrofuran; H₂O / 2 h 5.1: 6 percent / CuCl; pyridine; air / 24 h

Reference： [1]Baier, Martin; Gleiter, Rolf; Rominger, Frank [European Journal of Organic Chemistry, 2006, # 23, p. 5264 - 5278]

39
[ 26478-16-0 ]
1,12-diaza-4,9,15,20,25,30(2,5)-hexathiophenabicyclo[10.10.10]dotriacontaphane-5,7,16,18,26,28-hexayne [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: 80 percent / K₂CO₃ / acetonitrile / 64 h / Heating 2.1: n-BuLi / tetrahydrofuran / 0 - 20 °C 2.2: 61 percent / iodine / tetrahydrofuran / -78 - 20 °C 3.1: 99 percent / copper(I)iodide; Et₂N / tetrakis(triphenylphosphane)palladium⁽⁰⁾ / tetrahydrofuran / 1 h / 45 °C 4.1: 99 percent / NaOH / tetrahydrofuran; H₂O / 2 h 5.1: 2 percent / CuCl; pyridine; air / 24 h

Reference： [1]Baier, Martin; Gleiter, Rolf; Rominger, Frank [European Journal of Organic Chemistry, 2006, # 23, p. 5264 - 5278]

40
[ 26478-16-0 ]
C₃₀H₃₇NO₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: Mg / diethyl ether 1.2: 75 percent / benzene; diethyl ether / 3 h / Heating 2.1: 91 percent / CH₂Cl₂ / 5 h / Heating 3.1: 86 percent / KOH / bis-(2-hydroxy-ethyl) ether / 2 h / 205 - 210 °C 4.1: 31.2 percent / NaHCO₃ / dimethylformamide / 16 h / 70 - 80 °C

Reference： [1]Liu, He; Wang, Jingyan; Zhong, Bohua [Collection of Czechoslovak Chemical Communications, 2005, vol. 70, # 2, p. 237 - 246]

41
[ 26478-16-0 ]
[ 852050-14-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: Mg / diethyl ether 1.2: 75 percent / benzene; diethyl ether / 3 h / Heating 2.1: 91 percent / CH₂Cl₂ / 5 h / Heating 3.1: 86 percent / KOH / bis-(2-hydroxy-ethyl) ether / 2 h / 205 - 210 °C
	Multi-step reaction with 3 steps 1.1: magnesium / diethyl ether 1.2: 75 percent / diethyl ether; benzene / 3 h / Heating 2.1: 91 percent / CH₂Cl₂ / 5 h / Heating 3.1: 91 percent / potassium hydroxide / ethane-1,2-diol / 2 h / 205 - 210 °C

Reference： [1]Liu, He; Wang, Jingyan; Zhong, Bohua [Collection of Czechoslovak Chemical Communications, 2005, vol. 70, # 2, p. 237 - 246]
[2]Liu, Chun-He; Liu, He; Han, Xiang-Yu; Wu, Bo; Zhong, Bo-Hua; Gong, Ze-Hui [Synthetic Communications, 2005, vol. 35, # 5, p. 701 - 710]

42
[ 26478-16-0 ]
[ 852050-13-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: Mg / diethyl ether 1.2: 75 percent / benzene; diethyl ether / 3 h / Heating 2.1: 91 percent / CH₂Cl₂ / 5 h / Heating
	Multi-step reaction with 2 steps 1.1: magnesium / diethyl ether 1.2: 75 percent / diethyl ether; benzene / 3 h / Heating 2.1: 91 percent / CH₂Cl₂ / 5 h / Heating

43
[ 26478-16-0 ]
[ 852100-94-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: magnesium / diethyl ether 1.2: 75 percent / diethyl ether; benzene / 3 h / Heating 2.1: 91 percent / CH₂Cl₂ / 5 h / Heating 3.1: 91 percent / potassium hydroxide / ethane-1,2-diol / 2 h / 205 - 210 °C 4.1: 48 percent / sodium bicarbonate / dimethylformamide / 16 h / 70 - 80 °C

Reference： [1]Liu, Chun-He; Liu, He; Han, Xiang-Yu; Wu, Bo; Zhong, Bo-Hua; Gong, Ze-Hui [Synthetic Communications, 2005, vol. 35, # 5, p. 701 - 710]

44
[ 26478-16-0 ]
thienorphine-3-glucuronide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: magnesium / diethyl ether 1.2: 75 percent / diethyl ether; benzene / 3 h / Heating 2.1: 91 percent / CH₂Cl₂ / 5 h / Heating 3.1: 91 percent / potassium hydroxide / ethane-1,2-diol / 2 h / 205 - 210 °C 4.1: 48 percent / sodium bicarbonate / dimethylformamide / 16 h / 70 - 80 °C 5.1: 41 percent / lithium hydroxide monohydrate / methanol / 20 °C

Reference： [1]Liu, Chun-He; Liu, He; Han, Xiang-Yu; Wu, Bo; Zhong, Bo-Hua; Gong, Ze-Hui [Synthetic Communications, 2005, vol. 35, # 5, p. 701 - 710]

45
[ 26478-16-0 ]
[ 19995-41-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: Na / ethanol / 0.08 h / Heating 1.2: ethanol / 5 h / Heating 2.1: KOH / ethanol / 4 h / Heating 3.1: 3 h / 190 °C

Reference： [1]Nordin, Ove; Nguyen, Ba-Vu; Voerde, Carin; Hedenstroem, Erik; Hoegberg, Hans-Erik [Journal of the Chemical Society. Perkin Transactions 1 (2001), 2000, # 3, p. 367 - 376]

46
[ 26478-16-0 ]
[ 190507-30-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: Na / ethanol / 0.08 h / Heating 1.2: ethanol / 5 h / Heating 2.1: KOH / ethanol / 4 h / Heating 3.1: 3 h / 190 °C 4.1: 81 percent / LiAlH₄ / diethyl ether / 2 h / 20 °C

Reference： [1]Nordin, Ove; Nguyen, Ba-Vu; Voerde, Carin; Hedenstroem, Erik; Hoegberg, Hans-Erik [Journal of the Chemical Society. Perkin Transactions 1 (2001), 2000, # 3, p. 367 - 376]

47
[ 26478-16-0 ]
(S)-2-methyl-4-(thiophen-2-yl)butan-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: Na / ethanol / 0.08 h / Heating 1.2: ethanol / 5 h / Heating 2.1: KOH / ethanol / 4 h / Heating 3.1: 3 h / 190 °C 4.1: 81 percent / LiAlH₄ / diethyl ether / 2 h / 20 °C 5.1: CH₂=CHOAc / Amano PS / CHCl₃ / Enzymatic reaction 5.2: LiAlH₄ / diethyl ether / 1 h / 20 °C

Reference： [1]Nordin, Ove; Nguyen, Ba-Vu; Voerde, Carin; Hedenstroem, Erik; Hoegberg, Hans-Erik [Journal of the Chemical Society. Perkin Transactions 1 (2001), 2000, # 3, p. 367 - 376]

48
[ 26478-16-0 ]
(R)-2-Methyl-4-(2-thienyl)butan-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: Na / ethanol / 0.08 h / Heating 1.2: ethanol / 5 h / Heating 2.1: KOH / ethanol / 4 h / Heating 3.1: 3 h / 190 °C 4.1: 81 percent / LiAlH₄ / diethyl ether / 2 h / 20 °C 5.1: CH₂=CHOAc / Amano PS / CHCl₃ / Enzymatic reaction 5.2: LiAlH₄ / diethyl ether / 1 h / 20 °C

Reference： [1]Nordin, Ove; Nguyen, Ba-Vu; Voerde, Carin; Hedenstroem, Erik; Hoegberg, Hans-Erik [Journal of the Chemical Society. Perkin Transactions 1 (2001), 2000, # 3, p. 367 - 376]

49
[ 26478-16-0 ]
[ 19995-40-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: Na / ethanol / 0.08 h / Heating 1.2: ethanol / 5 h / Heating 2.1: KOH / ethanol / 4 h / Heating

Reference： [1]Nordin, Ove; Nguyen, Ba-Vu; Voerde, Carin; Hedenstroem, Erik; Hoegberg, Hans-Erik [Journal of the Chemical Society. Perkin Transactions 1 (2001), 2000, # 3, p. 367 - 376]

50
[ 26478-16-0 ]
[ 197094-81-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 78 percent / lithium diisopropylamide / tetrahydrofuran / 18 h / Heating 2: 1.) lithium aluminum hydride; 2.) hydrochloric acid / 1.) Et₂O, 0 deg C, 15 min

Reference： [1]Liu, Hsing-Jang; Tran, Duong Duc-Phi [Tetrahedron Letters, 1997, vol. 38, # 37, p. 6501 - 6504]

51
[ 26478-16-0 ]
[ 197094-82-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 78 percent / lithium diisopropylamide / tetrahydrofuran / 18 h / Heating 2: 1.) lithium aluminum hydride; 2.) hydrochloric acid / 1.) Et₂O, 0 deg C, 15 min 3: 71 percent / sodium hydride / tetrahydrofuran / 4 h / Heating

Reference： [1]Liu, Hsing-Jang; Tran, Duong Duc-Phi [Tetrahedron Letters, 1997, vol. 38, # 37, p. 6501 - 6504]

52
[ 26478-16-0 ]
5-[2-(4,5-Dibromo-4,5-dihydro-thiophen-2-yl)-ethyl]-5-methyl-2-oxo-cyclohex-3-enecarboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 78 percent / lithium diisopropylamide / tetrahydrofuran / 18 h / Heating 2: 1.) lithium aluminum hydride; 2.) hydrochloric acid / 1.) Et₂O, 0 deg C, 15 min 3: 71 percent / sodium hydride / tetrahydrofuran / 4 h / Heating 4: N-bromosuccinimide / CCl₄ / 2 h / Ambient temperature

Reference： [1]Liu, Hsing-Jang; Tran, Duong Duc-Phi [Tetrahedron Letters, 1997, vol. 38, # 37, p. 6501 - 6504]

53
[ 26478-16-0 ]
6,7-Dihydro-spiro<benzo<b>thiophen-5(4H),1'-cyclohexan>-4-on [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.) diisopropylamine, 1.57 M n-BuLi / 1.) THF, hexane, -10 deg C, 2.) r.t., 2 h 2: 81.5 percent / polyphosphoric acid / 2.5 h / 80 - 90 °C

Reference： [1]Stanetty, Peter [Journal of Chemical Research, Miniprint, 1981, # 5, p. 1784 - 1797]

54
[ 26478-16-0 ]
[ 61440-51-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 24 percent / hexamethylphosphoric acid triamide / 24 h / 125 °C 2: 42 percent / KOH / aq. ethanol / 5 h / Heating

Reference： [1]Albright; DeVries; Largis; Miner; Reich; Schaffer; Shepherd; Upeslacis [Journal of Medicinal Chemistry, 1983, vol. 26, # 10, p. 1378 - 1393]

55
[ 26478-16-0 ]
9-(4,5-dimethyl-thiazol-2-yl)-4-piperazin-1-yl-5,6,7,8-tetrahydro-1,3,4b-triaza-fluorene [ No CAS ]
[ 731824-93-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In acetonitrile for 4h; Heating / reflux;	2D Example 2D; 9-(4,5-Dimethyl-thiazol-2-yl)-4-[4-(2-thiophen-2-yl-ethyl)-piperazin-1-yl]-5,6,7, 8- TETRAHYDRO-1, 3, 4B-TRIAZA-FLUORENE To a solution of 2-(2-thienyl) ethanol (1.63g) in dry ether (15mL) at 0°C was added PBr3 (1. 31mL) dropwise. After 4 hours the reaction mixture was diluted with dichloromethane, washed with water, dried (MGS04) and the solvent removed in vacuo to yield a brown oil which was purified using flash chromatography to yield 2- (2-bromo-ethyl)-thiophene. A mixture of 9- (4, 5-DIMETHYL-THIAZOL-2-YL)-4-PIPERAZIN-1-YL-5, 6,7, 8-TETRAHYDRO- 1, 3, 4b-triaza-fluorene (85mg), 2- (2-bromo-ethyl)-thiophene (44mg) and potassium carbonate (38mg) was heated to reflux in acetonitrile (5ML) for 4 hours. The reaction mixture was cooled, extracted into dichloromethane, dried (MGS04) and the solvent removed in vacuo to yield crude product which was purified using flash chromatography to yield the title compound (30mg).

Reference： [1]Current Patent Assignee: XENOVA GMBH - WO2004/65389, 2004, A1 Location in patent: Page 47

56
[ 26478-16-0 ]
(R)-3-amino-5-phenylchroman [ No CAS ]
[ 584-08-7 ]
[ 170482-97-0 ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide	71 (R)-3-[N-2-(2-thienyl)ethyl]amino-5-phenylchroman hydrochloride. Example 71 (R)-3-[N-2-(2-thienyl)ethyl]amino-5-phenylchroman hydrochloride. To a solution of (R)-3-amino-5-phenylchroman (0.41 g, 1.83 mmol) in dry DMF (2.0 mL) were added K2 CO3 (0.28 g, 2.02 mmol) and 2-(2-thienyl) ethyl bromide (0.36 g, 1.80 mmol). The reaction mixture was stirred under N2 at 65° C. for 6 hours. The solvent was removed in vacuo and the residue was partitioned between ether (50 mL) and 1M NH3 -solution (10 mL). The layers were separated and the aqueous phase was saturated with NaCl (s) and extracted with an additional amount of ether (25 mL). The organic layers were combined, dried (MgSO4), filtered and concentrated. the residue was purified by column chromatography (eluent: hexane: EtOAc 65:35+0.2% conc. NH3) giving 0.19 g (31%) of the corresponding base of the title compound as a light yellow oil: [α]21=+8.2 (c=1.0, MeOH). Conversion to the hydrochloride was done in HCl/ether giving 0.20 g (total yield: 29%) of the title compound: mp 191.6°-193.2° C.

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - US5420151, 1995, A

57
[ 26478-16-0 ]
[ 109859-85-0 ]
[ 119918-09-1 ]

Yield	Reaction Conditions	Operation in experiment
43%		159 Prepared from 3-[(piperidin-3-yl)-methyl]-7,8-dimethoxy-2-oxo-1,3,4,5-tetrahydro-2H-3-benzazepine and 2-(2-bromo-ethyl)thiophene analogously to Example 1. EXAMPLE 159 3-[(N-(2-(Thien-2-yl)-ethyl)-piperidin-3-yl)-methyl]-7,8-dimethoxy-2-oxo-1,3,4,5-tetrahydro-2H-3-benzazepine-hydrochloride Prepared from 3-[(piperidin-3-yl)-methyl]-7,8-dimethoxy-2-oxo-1,3,4,5-tetrahydro-2H-3-benzazepine and 2-(2-bromo-ethyl)thiophene analogously to Example 1. Yield: 43% of theory, Melting point: 232°-236° C.

Reference： [1]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - US5175157, 1992, A

58
[ 26478-16-0 ]
2-(N-methyl-3-amino-propyl)-6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline [ No CAS ]
2-[N-Methyl-N-(2-(thien-2-yl)-ethyl)-3-amino-propyl]-6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In <i>N</i>-methyl-acetamide	1 2-[N-Methyl-N-(2-(thien-2-yl)-ethyl)-3-amino-propyl]-6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline hydrochloride EXAMPLE 1 2-[N-Methyl-N-(2-(thien-2-yl)-ethyl)-3-amino-propyl]-6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline hydrochloride 0.85 g (3.0 mmol) of 2-(N-methyl-3-amino-propyl)-6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydro-isoquinoline, 0.60 g (3.1 mmol) of 2-(2-bromo-ethyl)-thiophene and 5 ml of triethylamine are dissolved in 10 ml of dry dimethylformamide and heated to 100° C. for 4 hours. The reaction mixture is evaported down in vacuo and the residue is dissolved in a mixture of 2 molar sodium hydroxide solution and methylene chloride. The organic phase is separated off, washed with saturated saline solution, dried over sodium sulphate and evaporated down in vacuo. The crude product is purified by column chromatography (adsorption agent: silica gel, eluant: methylene chloride/methanol=10/1). The hydrochloride is precipitated from a solution in methanol with ethereal hydrochloric acid and then crystallized from acetone. Yield: 0.40 g (31% of theory), Melting point: 150°-151° C. Calculated: C 59.35 H 6.88 N 6.59 Cl 8.34 S 7.54. Found C 59.40 H 6.73 N 6.29 Cl 8.11 S 7.59.

Reference： [1]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - US4912115, 1990, A

59
[ 5402-55-1 ]
[ 7789-60-8 ]
[ 26478-16-0 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrachloromethane	2.A (5-(3-(((4-chlorophenyl)sulfonyl)amino)propylthien-2-yl)acetic acid A. 2-(2-Bromoethyl)thiophene. To a 65° C. solution of 2-(2-thienyl)ethanol(5.0 g, 39.0 mmol) in carbon tetrachloride (100 ml) was added, carefully in one portion, phosphorus (III) bromide (4.4 ml, 46.8 mmol). After stirring for 20 minutes, the reaction was cooled to room temperature and poured onto ice (ca. 100 g). The organic layer was separated. The aqueous layer was extracted with methylene chloride (3*50 ml). The four combined organic layers were washed (50 ml of saturated (NaHCO3) dried (Na2 SO4) and concentrated in vacuo to a volume of ca. 50 ml. The residue was distilled-first at atmospheric pressure to remove solvent-then in vacuo to provide the above titled compound as a transparent water-white liquid: 3.76 g (50%);

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US4752613, 1988, A

60
[ 5402-55-1 ]
[ 7789-60-8 ]
[ 26478-16-0 ]
[ 85918-84-9 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine In benzene	137 Ethyl 2-oxo-4-(2-thienyl)-butyrate EXAMPLE 137 Ethyl 2-oxo-4-(2-thienyl)-butyrate A mixture of phosphorous tribromide (18.95 g) and pyridine (3.76 cc) in 10 ml of benzene is chilled to -5° C. and treated with a solution of 2-(2-thienyl)-ethanol (25 g) in 10 ml of benzene containing 1.25 cc of pyridine at such a rate that the reaction temperature never exceeds 0° C. The mixture is then allowed to come to room temperature while stirring overnight. The reaction mixture is then concentrated on a water pump at 30°-40° C. to remove solvent and other volatiles, and the residue Claisen-distilled under water pump vacuum to yield 21 g of crude bromide (b.p. 115°-119° C.). This material is then fractionally distilled at 0.3 mm to provide 19 g of pure 2-(2-thienyl)-ethyl bromide (b.p. 50°-51° C.; 99.9% by gc).

Reference： [1]Current Patent Assignee: MERCK & CO INC - US4374829, 1983, A

61
[ 26478-16-0 ]
[ 41252-98-6 ]
[ 1080649-39-3 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 8705 - 8710

62
[ 26478-16-0 ]
[ 590-86-3 ]
[ 927835-82-3 ]

Yield	Reaction Conditions	Operation in experiment
30%	Stage #1: 2-(2-Bromoethyl)thiophene With magnesium In tetrahydrofuran for 4.16h; Heating / reflux; Stage #2: isovaleraldehyde In tetrahydrofuran at 0 - 20℃; for 18.5h; Stage #3: With hydrogenchloride In tetrahydrofuran; water	b One iodine crystal was added to a stirred suspension of magnesium turnings (45 mg, 1.85 mmol) in tetrahydrofuran (10 mL) then the mixture was heated at reflux. A solution of 2-(2-bromoethyl)thiophene (300 mg, 1.57 mmol) in tetrahydrofuran (3 mL) was added dropwise over 10 minutes then the mixture heated at reflux for 4 hours. The mixture was cooled to 0° C. then 3-methylbutanal (0.16 mL, 1.57 mmol) was added over 30 minutes then stirred at ambient temperature for 18 hours. Aqueous hydrochloric acid was added until pH<7 then the mixture was extracted with ethyl acetate (40 mL, 20 mL then 10 mL), then dried (NaSO4), filtered and reduced in vacuo. The residue was purified by flash chromatography over silica, eluting with ethyl acetate:hexane mixtures 2:98 to 4:96 to give 5-methyl-1-(thiophen-2-yl)hexan-3-ol as a colourless oil (93 mg, 30%). HPLC-MS 199.1 [M+H]+; δH (300 M , CDCl3) 0.90 (6H, m, CH(CH3)2), 1.10-1.90 (6H, m, CH2CH(OH)CH2), 2.75-3.00 (2H, m, CH2CH2C(OH)), 3.65 (1H, brs, OR), 6.75 (1H, m, SCHCHCH), 6.85 (1H, m, SCHCHCH), 7.00 (1H, d, J=4.5 Hz, SCHCHCH).

Reference： [1]Current Patent Assignee: AMURA HOLDINGS LIMITED - US2009/131502, 2009, A1 Location in patent: Page/Page column 26-27

63
[ 26478-16-0 ]
[ 14044-65-6 ]
[ 6372-48-1 ]
[ 1147564-59-7 ]

Yield	Reaction Conditions	Operation in experiment
84%	With NaOCH(CH₃)2CH₂CH₂ In tetrahydrofuran (N2); addn. of phosphine deriv. and benzyl chloride to THF soln. of sodium alcoholate deriv. and ruthenium compd., stirring at room temp. for 90min, addn. of THF soln. of borane deriv., stirring at room temp. for 30 min; addn. of water, extn. (ethyl acetate), washing with brine, drying over Na2SO4, filtration, concg., chromy. (silica gel, 70:30 hexanes/ethyl acetate);

Reference： [1]Chan, Vincent S.; Chiu, Melanie; Bergman, Robert G.; Toste, F. Dean [Journal of the American Chemical Society, 2009, vol. 131, p. 6021 - 6032]

64
[ 26478-16-0 ]
[ 6372-48-1 ]
C₁₃H₁₅PS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With [((R)-DIFLUORPHOS)(1,2-bis(dimethylphosphino)ethane)Ru(H)][BPh₄]; sodium tert-pentoxide In tetrahydrofuran at 23℃; for 1.5h; Inert atmosphere;

Reference： [1]Chan, Vincent S.; Chiu, Melanie; Bergman, Robert G.; Toste, F. Dean [Journal of the American Chemical Society, 2009, vol. 131, p. 6021 - 6032]

65
[ 26478-16-0 ]
[ 73183-34-3 ]
[ 1361022-77-6 ]

Yield	Reaction Conditions	Operation in experiment
63%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium phosphate monohydrate; di-tert-butyl(methyl)phosphonium tetrafluoroborate salt In water; <i>tert</i>-butyl alcohol at 60℃; Inert atmosphere;
57%	With chlorotris(triphenylphosphine)cobalt(I); sodium ethanolate; 1,3-dicyclohexylimidazol-2-ylidene In tert-butyl methyl ether at 50℃; for 16h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Joshi-Pangu, Amruta; Ma, Xinghua; Diane, Mohamed; Iqbal, Sidra; Kribs, Robert J.; Huang, Richard; Wang, Chao-Yuan; Biscoe, Mark R. [Journal of Organic Chemistry, 2012, vol. 77, # 15, p. 6629 - 6633]
[2]Geetharani, K.; Prasad, K. Sujit; Varghese, Dominic; Verma, Piyush Kumar [Organic Letters, 2020, vol. 22, # 4, p. 1431 - 1436]

66
[ 26478-16-0 ]
[ 615-81-6 ]
[ 1572201-15-0 ]

Yield	Reaction Conditions	Operation in experiment
89%	Stage #1: 2-(2-Bromoethyl)thiophene With magnesium In tetrahydrofuran at 20℃; for 1.25h; Inert atmosphere; Stage #2: diisopropyl oxalate In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;

Reference： [1]Corbett, Michael T.; Johnson, Jeffrey S. [Angewandte Chemie - International Edition, 2014, vol. 53, # 1, p. 255 - 259][Angew. Chem., 2013, vol. 126, # 1, p. 259 - 263,5]

67
[ 26478-16-0 ]
[ 1572201-40-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: magnesium / tetrahydrofuran / 1.25 h / 20 °C / Inert atmosphere 1.2: 1 h / -78 °C / Inert atmosphere 2.1: copper(ll) bromide / chloroform; ethyl acetate / 12 h / Reflux

Reference： [1]Corbett, Michael T.; Johnson, Jeffrey S. [Angewandte Chemie - International Edition, 2014, vol. 53, # 1, p. 255 - 259][Angew. Chem., 2013, vol. 126, # 1, p. 259 - 263,5]

68
[ 26478-16-0 ]
[ 1572201-80-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: magnesium / tetrahydrofuran / 1.25 h / 20 °C / Inert atmosphere 1.2: 1 h / -78 °C / Inert atmosphere 2.1: copper(ll) bromide / chloroform; ethyl acetate / 12 h / Reflux 3.1: (S)-(6-hydroxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl 2-methylbenzoate / 2-methyltetrahydrofuran / 18 h / 20 °C

Reference： [1]Corbett, Michael T.; Johnson, Jeffrey S. [Angewandte Chemie - International Edition, 2014, vol. 53, # 1, p. 255 - 259][Angew. Chem., 2013, vol. 126, # 1, p. 259 - 263,5]

69
[ 26478-16-0 ]
[ 1572202-14-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: magnesium / tetrahydrofuran / 1.25 h / 20 °C / Inert atmosphere 1.2: 1 h / -78 °C / Inert atmosphere 2.1: copper(ll) bromide / chloroform; ethyl acetate / 12 h / Reflux 3.1: 4-nitro-benzoic acid; 9-amino-9-deoxyepicinchonidine / 3 h / 20 °C

Reference： [1]Corbett, Michael T.; Johnson, Jeffrey S. [Angewandte Chemie - International Edition, 2014, vol. 53, # 1, p. 255 - 259][Angew. Chem., 2013, vol. 126, # 1, p. 259 - 263,5]

70
[ 26478-16-0 ]
isopropyl 3-bromo-2-hydroxy-2-(nitromethyl)-4-(thiophen-2-yl)butanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: magnesium / tetrahydrofuran / 1.25 h / 20 °C / Inert atmosphere 1.2: 1 h / -78 °C / Inert atmosphere 2.1: copper(ll) bromide / chloroform; ethyl acetate / 12 h / Reflux 3.1: N-ethyl-N,N-diisopropylamine / 2-methyltetrahydrofuran / 18 h / 20 °C

Reference： [1]Corbett, Michael T.; Johnson, Jeffrey S. [Angewandte Chemie - International Edition, 2014, vol. 53, # 1, p. 255 - 259][Angew. Chem., 2013, vol. 126, # 1, p. 259 - 263,5]

71
[ 26478-16-0 ]
isopropyl 2-(1-bromo-2-(thiophen-2-yl)ethyl)-2-hydroxy-4-oxopentanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: magnesium / tetrahydrofuran / 1.25 h / 20 °C / Inert atmosphere 1.2: 1 h / -78 °C / Inert atmosphere 2.1: copper(ll) bromide / chloroform; ethyl acetate / 12 h / Reflux 3.1: rac-Pro-OH / 3 h / 20 °C

Reference： [1]Corbett, Michael T.; Johnson, Jeffrey S. [Angewandte Chemie - International Edition, 2014, vol. 53, # 1, p. 255 - 259][Angew. Chem., 2013, vol. 126, # 1, p. 259 - 263,5]

72
[ 26478-16-0 ]
[ 768-60-5 ]
2-(4-(4-methoxyphenyl)but-3-yn-1-yl)thiophene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-methoxyphenylacetylen With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; Stage #2: 2-(2-Bromoethyl)thiophene With sodium iodide In tetrahydrofuran; hexane at 20℃; Reflux;

Reference： [1]Xu, Jun; Wang, Yun-Long; Gong, Tian-Jun; Xiao, Bin; Fu, Yao [Chemical Communications, 2014, vol. 50, # 85, p. 12915 - 12918]

73
[ 26478-16-0 ]
[ 103-67-3 ]
C₁₄H₁₃NOS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93.8%	With 4-methyl-morpholine; bis(tricyclohexylphosphine)nickel(II) dichloride; 5,10,15,20-tetraphenyl-21H,23H-porphine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In N,N-dimethyl-formamide at 20 - 75℃; for 10h;	1 Example 1 At room temperature, the appropriate amount of solvent (volume ratio 4: N 1 is, of N- dimethylformamide (DMF)A mixture of polyethylene glycol (PEG-200)) is added (I) compound, 170 100mmol ceremonyMmol compound of formula (II),15mmol catalyst (13.5mmol as strontium bromide and 1.5mmol1- (1- ferrocenyl ethyl) -3-isopropyl-1-imidazole salt mixture),200mmol oxidant 2- iodoxybenzoic acid (IBX),130mmolAlkali N- methylmorpholine,35mmol additive bis (tricyclohexylphosphine) nickel chloride (NiCl2 (PCy3) 2) and 12mmol activator tetraphenylporphyrin;Then stirred heated to 75 ,And the reaction was stirred at this temperature for 10 hours;After completion of the reaction, the reaction solution was cooled to room temperature, saturated aqueous sodium bicarbonate was addedWas washed thoroughly shaking, extracted with dichloromethane, the organic phase was separated, which was dried over anhydrous sulfateMagnesium sulfate, and concentrated in vacuo, the resulting residue was purified through silica gel column chromatography to volume ratio of acetone and the likeRinse mixture of chloroform, to afford the compound of formula (III), a yield of 93.8%.

Reference： [1]Current Patent Assignee: Gao, Yuhua - CN105777728, 2016, A Location in patent: Paragraph 0037; 0038; 0039; 0040; 0041

74
[ 26478-16-0 ]
[ 101403-24-1 ]
[ 1148154-91-9 ]

Yield	Reaction Conditions	Operation in experiment
88%	With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 4h; Inert atmosphere; Green chemistry;
2.69 g	With sodium carbonate In N,N-dimethyl-formamide at 70℃; for 4h;	1.3 The chiral compound (II)(S) -2- (N-n-propyl) amino-5-methoxytetrahydronaphthalene 2.12 g,2- (2-bromoethyl) thiophene, 3.75 g,DMF 20 mL,Anhydrous sodium carbonate,Added to the reaction flask,Heating at 70 ° C for 4 hours,filter,The liquid was slowly added to 200 mL of ice water,Ethyl acetate 60mL extraction three times,Combined organic layer,The organic layer was washed with 50 mL of water,Dried over anhydrous sodium sulfate,The solvent was distilled off,To give 2.69 g of the pale yellow oily compound (III).

Reference： [1]Current Patent Assignee: ANHUI QINGYUN MEDICINE - CN109574983, 2019, A Location in patent: Paragraph 0061; 0114-0119; 0157-0162; 0170; 0200-0205; 0218
[2]Current Patent Assignee: HENAN ACADEMY OF SCIENCES - CN104130238, 2016, B Location in patent: Paragraph 0036; 0040

75
5-isobutyl-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione [ No CAS ]
[ 26478-16-0 ]
5-isobutyl-1,3-dimethyl-5-(2-(thiophen-2-yl)ethyl)pyrimidine-2,4,6(1H,3H,5H)-trione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	With potassium carbonate In tetrahydrofuran at 20℃; for 8h; Inert atmosphere;

Reference： [1]Huang, Huan-Ming; Procter, David J. [European Journal of Organic Chemistry, 2019, vol. 2019, # 2, p. 313 - 317]

76
5-isobutyl-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione [ No CAS ]
[ 26478-16-0 ]
5-isobutyl-1,3-dimethyl-5-(2-(thiophen-2-yl)ethyl)dihydropyrimidine-4,6(1H,5H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate / tetrahydrofuran / 8 h / 20 °C / Inert atmosphere 2: samarium diiodide; lithium bromide; water / tetrahydrofuran / 8 h / 20 °C / Inert atmosphere

Reference： [1]Huang, Huan-Ming; Procter, David J. [European Journal of Organic Chemistry, 2019, vol. 2019, # 2, p. 313 - 317]

77
[ 26478-16-0 ]
[ 927208-27-3 ]

Yield	Reaction Conditions	Operation in experiment
	With chlorosulfonic acid In dichloromethane at 0 - 20℃; for 3h;

Reference： [1]Meiers, Joscha; Zahorska, Eva; Röhrig, Teresa; Hauck, Dirk; Wagner, Stefanie; Titz, Alexander [Journal of Medicinal Chemistry, 2020, vol. 63, # 20, p. 11707 - 11724]

78
[ 26478-16-0 ]
C₁₃H₂₀BrNO₆S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: chlorosulfonic acid / dichloromethane / 3 h / 0 - 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 0 - 20 °C

Reference： [1]Meiers, Joscha; Zahorska, Eva; Röhrig, Teresa; Hauck, Dirk; Wagner, Stefanie; Titz, Alexander [Journal of Medicinal Chemistry, 2020, vol. 63, # 20, p. 11707 - 11724]

79
[ 26478-16-0 ]
N-β-L-fucopyranosylmethyl-2-(5-(2′-azidoethyl)thiophene)-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: chlorosulfonic acid / dichloromethane / 3 h / 0 - 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 0 - 20 °C 3: sodium azide / N,N-dimethyl-formamide / 3 h / 20 °C

Reference： [1]Meiers, Joscha; Zahorska, Eva; Röhrig, Teresa; Hauck, Dirk; Wagner, Stefanie; Titz, Alexander [Journal of Medicinal Chemistry, 2020, vol. 63, # 20, p. 11707 - 11724]

80
[ 26478-16-0 ]
C₃₃H₄₀FN₇O₉S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: chlorosulfonic acid / dichloromethane / 3 h / 0 - 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 0 - 20 °C 3: sodium azide / N,N-dimethyl-formamide / 3 h / 20 °C 4: copper(II) sulfate heptahydrate; sodium L-ascorbate / N,N-dimethyl-formamide; water / 16 h / 40 °C / Inert atmosphere

Reference： [1]Meiers, Joscha; Zahorska, Eva; Röhrig, Teresa; Hauck, Dirk; Wagner, Stefanie; Titz, Alexander [Journal of Medicinal Chemistry, 2020, vol. 63, # 20, p. 11707 - 11724]

81
[ 26478-16-0 ]
C₃₄H₄₂FN₇O₉S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: chlorosulfonic acid / dichloromethane / 3 h / 0 - 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 0 - 20 °C 3: sodium azide / N,N-dimethyl-formamide / 3 h / 20 °C 4: copper(II) sulfate heptahydrate; sodium L-ascorbate / N,N-dimethyl-formamide; water / 16 h / 40 °C / Inert atmosphere

Reference： [1]Meiers, Joscha; Zahorska, Eva; Röhrig, Teresa; Hauck, Dirk; Wagner, Stefanie; Titz, Alexander [Journal of Medicinal Chemistry, 2020, vol. 63, # 20, p. 11707 - 11724]

82
[ 26478-16-0 ]
C₁₂H₁₈ClNO₂Si [ No CAS ]
[ 141109-20-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In acetonitrile at 70 - 80℃;	1.2; 2.2; 3.2 Synthesis of (S)-2-thiopheneethylamino-2-chlorophenylacetic acid methyl ester hydrochloride In a three-necked bottle, 40.1g (0.1393mol) trimethylsilyl protected (S)-o-chlorophenylglycine methyl ester,28.9g (0.2090mol) superfine powdered potassium carbonate,Add 521.3g of acetonitrile to the reaction flask,Add 29.1g (0.1407mol) 2-(2-bromoethyl)thiophene in batches,Heating at 7080, the system will reflux and keep warm for reaction,Part of acetonitrile is distilled off every 4 hours, and after 8 to 16 hours of reaction,The reaction conversion rate reaches 98%, stop heating and slowly cool down,Take the reaction liquid to test, the dialkylated impurity is 0.46%,The optical isomer content is 1.8%.T inner=5057, transfer the reaction solution into a single-neck bottle,At -0.08-0.09MPa, 5070,The solvent was evaporated, 160g water and 201g methyl acetate were added for extraction,Wash with water to obtain a methyl acetate solution of methyl (S)-2-thiopheneethylamino-2-chlorophenylacetate,Control the temperature and add concentrated hydrochloric acid until the system is acidic.The off-white solid is separated out, filtered, and the filter cake is rinsed with methyl acetate.Dry the filter cake at 5060,48.2g of crude (S)-2-thiopheneethylamino-2-chlorophenylacetic acid methyl ester hydrochloride (theoretical yield 48.2g) was obtained.48.2g (S)-2-thiopheneethylamino-2-chlorophenylacetic acid methyl ester hydrochloride crude product is mixed with 179g acetonitrile and 13.5g ethanol,Beat at 50-60 for more than 1 hour,Cool down to 6-10, keep warm for more than 1 hour,Suction filtration, drying the filter cake at 5060,Obtained 47.5 g of (S)-2-thiopheneethylamino-2-chlorophenylacetic acid methyl ester hydrochloride,Yield 98.5%, HPLC purity 99.91%,The content of optical isomers is 0.12%,The content of dialkylated impurities is 0.048%.

Reference： [1]Current Patent Assignee: VALIANT CO., LTD. - CN112341475, 2021, A Location in patent: Paragraph 0075; 0078-0079; 0082; 0085-0086; 0089; 0092-0093

83
[ 26478-16-0 ]
[ 25015-63-8 ]
[ 1361022-77-6 ]

Yield	Reaction Conditions	Operation in experiment
82%	With chromium chloride; aluminium; 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuran at 80℃; for 15h; Schlenk technique; Inert atmosphere;

Reference： [1]Fu, Aiping; Li, Chao; Luo, Meiming; Zeng, Xiaoming; Zhao, Lixing [Organometallics, 2021, vol. 40, # 14, p. 2204 - 2208]

84
[ 26478-16-0 ]
C₉H₉ClOS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 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 3.1: diethylamine; formaldehyd / ethyl acetate / 12.5 h / 0 - 85 °C 4.1: phosgene / dichloromethane; N,N-dimethyl-formamide / 2 h / 0 °C

Reference： [1]Dong, Kaiwu; Ren, Xinyi; Shen, Chaoren; Wang, Guangzhu [Chemical Communications, 2022, vol. 58, # 8, p. 1135 - 1138]

85
[ 26478-16-0 ]
C₉H₁₀O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 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 3.1: diethylamine; formaldehyd / ethyl acetate / 12.5 h / 0 - 85 °C

Reference： [1]Dong, Kaiwu; Ren, Xinyi; Shen, Chaoren; Wang, Guangzhu [Chemical Communications, 2022, vol. 58, # 8, p. 1135 - 1138]

86
[ 26478-16-0 ]
(2-[2]thienyl-ethyl)-malonic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	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]Dong, Kaiwu; Ren, Xinyi; Shen, Chaoren; Wang, Guangzhu [Chemical Communications, 2022, vol. 58, # 8, p. 1135 - 1138]

87
[ 26478-16-0 ]
2-(1-(cyclopropylmethyl)-2-oxo-3-(2-(thiophen-2-yl)ethyl)indolin-3-yl)acetonitrile [ No CAS ]
2-(1-(cyclopropylmethyl)-2-oxo-3-(2-(thiophen-2-yl)ethyl)indolin-3-yl)acetonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 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 3.1: diethylamine; formaldehyd / ethyl acetate / 12.5 h / 0 - 85 °C 4.1: phosgene / dichloromethane; N,N-dimethyl-formamide / 2 h / 0 °C 5.1: triethylamine / dichloromethane / 6 h / 0 - 20 °C 6.1: nickel dibromide; zinc; (2S,4S)-2,4-bis(diphenylphosphino)pentane / N,N-dimethyl acetamide; tetrahydrofuran / 12 h / 80 °C / Schlenk technique; Glovebox; Inert atmosphere

Reference： [1]Dong, Kaiwu; Ren, Xinyi; Shen, Chaoren; Wang, Guangzhu [Chemical Communications, 2022, vol. 58, # 8, p. 1135 - 1138]

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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. 26478-16-0 ] {[proInfo.proName]}

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[ 26478-16-0 ] Synthesis Path-Downstream 1~87

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