[ CAS No. 89043-32-3 ] {[proInfo.proName]}

Name: 89043-32-3|1-Bromo-4-(t-butyldimethylsilyloxy)butane|97%
Brand: Ambeed
SKU: A628803
Price: 7.0 USD
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2D 3D

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Quality Control of [ 89043-32-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 89043-32-3 ]

SDS Specification

Alternatived Products of [ 89043-32-3 ]

Product Details of [ 89043-32-3 ]

CAS No. :	89043-32-3	MDL No. :	MFCD20259686
Formula :	C₁₀H₂₃BrOSi	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YORLKVKBZRVNMZ-UHFFFAOYSA-N
M.W :	267.28	Pubchem ID :	582370
Synonyms :

Calculated chemistry of [ 89043-32-3 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	6
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	67.01
TPSA :	9.23 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.86 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.57
Log Po/w (XLOGP3) :	4.33
Log Po/w (WLOGP) :	4.18
Log Po/w (MLOGP) :	3.27
Log Po/w (SILICOS-IT) :	2.06
Consensus Log Po/w :	3.48

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.83
Solubility :	0.0396 mg/ml ; 0.000148 mol/l
Class :	Soluble
Log S (Ali) :	-4.24
Solubility :	0.0154 mg/ml ; 0.0000578 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-4.18
Solubility :	0.0176 mg/ml ; 0.0000658 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	4.53

Safety of [ 89043-32-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 89043-32-3 ]

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

Downstream synthetic route of [ 89043-32-3 ]

[ 89043-32-3 ] Synthesis Path-Downstream 1~88

1
[ 79368-02-8 ]
[ 89043-32-3 ]
[ 133568-13-5 ]

Reference： [1]Tetrahedron,1991,vol. 47,p. 383 - 402

2
[ 917-92-0 ]
[ 89043-32-3 ]
[ 1027551-25-2 ]

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 610 - 615

3
[ 2158-59-0 ]
[ 89043-32-3 ]
2-[4-(tert-Butyl-dimethyl-silanyloxy)-butyl]-4-isopropyl-cyclohexanone [ No CAS ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1995,p. 955 - 956

4
[ 609-14-3 ]
[ 89043-32-3 ]
[ 189047-11-8 ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 2944 - 2956

5
[ 5707-04-0 ]
[ 89043-32-3 ]
[ 221298-47-1 ]

Reference： [1]Tetrahedron Letters,1997,vol. 38,p. 5197 - 5200

6
[ 42908-34-9 ]
[ 89043-32-3 ]
[2-[4-(tert-Butyl-dimethyl-silanyloxy)-butyl]-cyclopent-(E)-ylidene]-cyclohexyl-amine [ No CAS ]

Reference： [1]Tetrahedron Letters,1997,vol. 38,p. 5197 - 5200

7
[ 33036-62-3 ]
[ 18162-48-6 ]
[ 89043-32-3 ]

Yield	Reaction Conditions	Operation in experiment
	With 1H-imidazole; In N,N-dimethyl-formamide; at 20℃;	TBSCl (452 mg, 3.0 mmol) and imidazole (204 mg, 3.0 mmol) were added to a solution of4- bromobutanol (300 mg, 2.0 mmol) in DMF (3 mL) at room temperature. After stirring overnight,the resulting mixture was poured into ice-water, and extracted with EtOAc. The organic layer waswashed with saturated aqueous NaHCO3 and NaCl successively, dried over Na2SO4, filtered, andconcentrated in vacuo to give Br(CH2)4OTBS crude. The crude was dissolved in acetone (3 mL), then23 (225 mg, 0.5 mmol) and K2CO3 (276 mg, 2 mmol) were added. The reaction mixture was thenrefluxed overnight and concentrated in vacuo. The residue was purified by column chromatography(petroleum ether/acetone = 7:1) to give 24 as yellow solid (136 mg, 42.8%).

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 9977 - 9983
[2]Chemical Communications,2017,vol. 53,p. 3535 - 3538
[3]Organic Letters,2018,vol. 20,p. 6938 - 6942
[4]European Journal of Organic Chemistry,2020
[5]Journal of Organic Chemistry,1999,vol. 64,p. 6960 - 6968
[6]Journal of the American Chemical Society,2002,vol. 124,p. 10274 - 10275
[7]Russian Journal of General Chemistry,2011,vol. 81,p. 2142 - 2150
[8]Organic Letters,2011,vol. 13,p. 740 - 743
[9]Journal of Medicinal Chemistry,2008,vol. 51,p. 5690 - 5701
[10]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 7475 - 7485
[11]International Journal of Nanomedicine,2019,vol. 14,p. 6325 - 6337
[12]Molecules,2020,vol. 25

8
[ 89043-32-3 ]
5-(Diphenyl-hydrazono)-pentanal [ No CAS ]
[ 246143-53-3 ]

Reference： [1]Journal of Organic Chemistry,1999,vol. 64,p. 6960 - 6968

9
[ 42908-34-9 ]
[ 89043-32-3 ]
[ 181641-13-4 ]

Reference： [1]Journal of Organic Chemistry,1999,vol. 64,p. 1259 - 1264

10
[ 87184-99-4 ]
[ 89043-32-3 ]

Reference： [1]Tetrahedron Letters,2000,vol. 41,p. 6049 - 6052
[2]Chemical and Pharmaceutical Bulletin,2005,vol. 53,p. 1333 - 1334
[3]Molecules,2004,vol. 9,p. 541 - 549

11
[ 91647-85-7 ]
[ 89043-32-3 ]
[ 475207-21-7 ]

Reference： [1]Journal of Natural Products,2002,vol. 65,p. 1715 - 1718

12
[ 930-68-7 ]
[ 89043-32-3 ]
[ 481658-42-8 ]

Reference： [1]Tetrahedron,2003,vol. 59,p. 3385 - 3395

13
[ 1193-18-6 ]
[ 89043-32-3 ]
2-[4-(tert-butyl-dimethyl-silanyloxy)-butyl]-3-methyl-cyclohex-2-enone [ No CAS ]

Reference： [1]Tetrahedron,2003,vol. 59,p. 3385 - 3395

14
[ 33036-62-3 ]
[ 58479-61-1 ]
[ 89043-32-3 ]

Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 13132 - 13142

15
[ 89043-32-3 ]
[ 15448-47-2 ]
[ 465519-00-0 ]

Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 13132 - 13142
[2]Chemistry - A European Journal,2004,vol. 10,p. 2214 - 2222
[3]Journal of the American Chemical Society,2002,vol. 124,p. 10274 - 10275

16
[ 89043-32-3 ]
[ 706822-65-3 ]
[ 706822-66-4 ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 3761 - 3763

17
[ 879-37-8 ]
[ 89043-32-3 ]
2-{1-[4-(tert-butyl-dimethyl-silanyloxy)-butyl]-1H-indol-3-yl}-acetamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5171 - 5174

18
[ 107-86-8 ]
[ 89043-32-3 ]
[ 850095-06-6 ]

Reference： [1]Molecules,2004,vol. 9,p. 541 - 549

19
[ 16724-63-3 ]
[ 89043-32-3 ]
[ 1025992-80-6 ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 5721 - 5728

20
[ 98602-83-6 ]
[ 89043-32-3 ]

Reference： [1]Molecules,2004,vol. 9,p. 541 - 549

21
[ 405939-84-6 ]
[ 89043-32-3 ]
[6-(5-{tert-butoxycarbonyl-[4-(tert-butyl-dimethyl-silanyloxy)-butyl]-amino}-pyridin-3-yl)-pyrazin-2-yl]-(3-chloro-phenyl)-carbamic acid tert-butyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 4892 - 4909

22
[ 89043-32-3 ]
[ 603-35-0 ]
[ 87436-78-0 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,2005,vol. 53,p. 1333 - 1334

23
[ 907190-28-7 ]
[ 89043-32-3 ]
5-[4-(tert-butyl-dimethyl-silanyloxy)-butoxy]-3-(3,5-dichloro-phenyl)-1-naphthalen-2-yl-1H-pyrazole [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 807 - 813

24
[ 89043-32-3 ]
[ 954110-33-9 ]

Yield	Reaction Conditions	Operation in experiment
		Preparation 34; To a solution of [l-methyl-5- (tritylamino) -lH-pyrazol-4- yl]formamide (12.47 g) in DMF (dimethylformamide: 125 ml) was added portionwise sodium hydride (60% dispersion in mineral oil, 1.43 g) under ice-cooling. The mixture was stirred at room temperature for 1 hour. To the reaction mixture were added (4-bromobutoxy) (tert-butyl) dimethylsilane '(9.20 g) and NaI (5.38 g) at room temperature, and the mixture was stirred overnight at the same temperature . The resulting mixture was poured into water, and extracted with EtOAc (ethyl acetate) . The organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residual solid was purified column chromatography on silica gel to give (4- { [tert-butyl (dimethyl) silyl] oxy}butyl) [l-methyl-5- (tritylamino) -lH-pyrazol-4-yl] formamide (7.80 g) as an amorphous solid. 1H-NMR '(DMSO-Ci6) delta theta.00 (6H, s) , 0.83 (9H, s) , 1.20-1.40 (4H, m) , 2.70-2.95 (2H, m) , 2.74 (3H, s) , 3.45-3.55 (2H, m) , 6.02 (IH, s) , 7.00-7.35 (16H, m) , 7.59 (IH, s)

Reference： [1]Patent: WO2007/119511,2007,A1 .Location in patent: Page/Page column 73

25
[ 2758-18-1 ]
[ 89043-32-3 ]
2-(4-t-butyldimethylsilyloxybutyl)-3-methylcyclopent-2-en-1-one [ No CAS ]

Reference： [1]Heterocycles,2007,vol. 72,p. 517 - 528

26
[ 949008-55-3 ]
[ 89043-32-3 ]
C₂₅H₃₂BrF₂NO₃Si [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 5912 - 5949

27
[ 18162-48-6 ]
MeHal [ No CAS ]
[ 89043-32-3 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,2005,vol. 53,p. 1333 - 1334

28
[ 89043-32-3 ]
[ 465519-01-1 ]

Reference： [1]Chemistry - A European Journal,2004,vol. 10,p. 2214 - 2222
[2]Journal of the American Chemical Society,2003,vol. 125,p. 13132 - 13142
[3]Journal of the American Chemical Society,2002,vol. 124,p. 10274 - 10275

29
[ 89043-32-3 ]
(E)-tert-butyldimethyl((7-methylocta-5,7-dien-1-yl)oxy)silane [ No CAS ]

Reference： [1]Molecules,2004,vol. 9,p. 541 - 549

30
[ 89043-32-3 ]
8-t-butyldimethylsilyloxy-2-methyl-2-octen-4-one [ No CAS ]

Reference： [1]Molecules,2004,vol. 9,p. 541 - 549

31
[ 89043-32-3 ]
3-{1-[4-(tert-butyl-dimethyl-silanyloxy)-butyl]-1H-indol-3-yl}-4-hydroxy-pyrrole-2,5-dione [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5171 - 5174

32
[ 89043-32-3 ]
3-{1-[4-(tert-butyl-dimethyl-silanyloxy)-butyl]-1H-indol-3-yl}-4-phenylamino-pyrrole-2,5-dione [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5171 - 5174

33
[ 89043-32-3 ]
[ 246143-54-4 ]

Reference： [1]Journal of Organic Chemistry,1999,vol. 64,p. 6960 - 6968

34
[ 89043-32-3 ]
trans-2-(4-tert-butyldimethylsilyloxybutyl)-1-(N,N-diphenylhydrazino)cyclopentane [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1999,vol. 64,p. 6960 - 6968

35
[ 89043-32-3 ]
cis-2-(4-tert-butyldimethylsilyloxybutyl)-1-(N,N-diphenylhydrazino)cyclopentane [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1999,vol. 64,p. 6960 - 6968

36
[ 89043-32-3 ]
[ 221298-47-1 ]

Reference： [1]Journal of Organic Chemistry,1999,vol. 64,p. 1259 - 1264

37
[ 89043-32-3 ]
2-[4-(tert-butyl-dimethyl-silanyloxy)-butyl]-5-phenylselanyl-cyclopentanone [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1999,vol. 64,p. 1259 - 1264

38
[ 89043-32-3 ]
[ 1026500-47-9 ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 2944 - 2956

39
[ 89043-32-3 ]
[ 189047-13-0 ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 2944 - 2956

40
[ 89043-32-3 ]
[ 164931-68-4 ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1995,p. 955 - 956

41
[ 89043-32-3 ]
Trifluoro-methanesulfonic acid 2-[4-(tert-butyl-dimethyl-silanyloxy)-butyl]-4-isopropyl-cyclohex-1-enyl ester [ No CAS ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1995,p. 955 - 956

42
[ 89043-32-3 ]
[ 133568-14-6 ]

Reference： [1]Tetrahedron,1991,vol. 47,p. 383 - 402

43
[ 895541-85-2 ]
[ 89043-32-3 ]
[ 895542-85-5 ]

Yield	Reaction Conditions	Operation in experiment
99%	With caesium carbonate; In N,N-dimethyl-formamide; at 20 - 80℃; for 18h;	1 g of ethyl 3"-t°rf-butyl-4"-diethylamino-4l-hydroxy[1 ,1';3',1"]terphenyl-4-carboxylate obtained in Example 1d (2.2 mmol) are dissolved in 20 mL of dimethylformamide under a nitrogen atmosphere. 880 mg (2.7 mmol) of caesium carbonate are added. The reaction medium stirred at room temperature turns yellow. 0.64 mL of 1-bromo-4-(te/f- butyldimethylsilanyloxy)butane (2.4 mmol) is then added and the reaction medium is heated at 8O0C for 18 hours. The reaction medium is then cooled to room temperature and then filtered. The solvents are evaporated off and the residue obtained is purified by chromatography on silica gel (eluent: 70/30 heptane/ethyl acetate). EPO <DP n="23"/>1.4 g of ethyl 3"-terf-butyl-4l-[4-(tert-butyldimethylsilanyloxy)butoxy]-4"-diethylamino- [1,1';3',1"]terphenyl-4-carboxylate are obtained (yield = 99%) in the form of an oil.

Reference： [1]Patent: WO2006/66978,2006,A1 .Location in patent: Page/Page column 21-22

44
[ 950514-40-6 ]
[ 89043-32-3 ]
[ 950514-41-7 ]

Yield	Reaction Conditions	Operation in experiment
24%	With sodium hydride; In tetrahydrofuran; at 65℃; for 16h;	[[4-(tert-Butyl-dimethyl-silanyloxy)-butyl]-(5-ethyl-pyrimidin-2-yl)-(4-trifluoromethyl-phenyl)]amine: To a solution of 2 (5-ethyl-pyrimidin-2-yl)-(4-trifluoromethoxy-phenyl)amine (252 mg, 0.89 mmol) and <strong>[89043-32-3](4-bromo-butoxy)-tert-butyl-dimethylsilane</strong> (285 mg, 1.07 mmol) in THF (10 mL) was added NaH (60% in mineral oil) (54 mg, 1.34 mmol). The resulting mixture was heated to 65 C. under N2 with stirring. After heating for 16 h, the reaction mixture was cooled to room temperature, quenched with water (10 mL) and extracted with ethyl acetate (25 mL*2). The combined organic layers were washed with water, brine and then dried over Na2SO4. After removal of solvent, the crude product was purified by silica gel chromatography to give 100 mg (24%) of the desired product. 1H NMR (400 MHz, CDCl3) delta 8.17 (s, 2H), 7.29 (d, 2H), 7.22 (d, 2H), 3.98 (t, 2H), 3.61 (t, 2H), 2.47 (q, 2H), 1.68 (m, 2H), 1.55 (m, 2H), 1.15 (t, 3H), 0.85 (s, 9H), 0.01 (s, 6H).

Reference： [1]Patent: US2007/219193,2007,A1 .Location in patent: Page/Page column 19

45
[ 89043-32-3 ]
[ 157428-24-5 ]
[ 1058146-44-3 ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 5690 - 5701

46
[ 89043-32-3 ]
[ 156897-72-2 ]
[ 1058146-41-0 ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 5690 - 5701

47
[ 765-03-7 ]
[ 89043-32-3 ]
[ 1256346-65-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 7475 - 7485

48
[ 89043-32-3 ]
[ 95-92-1 ]
[ 253437-61-5 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 740 - 743

49
[ 764-32-9 ]
[ 89043-32-3 ]
[ 1332447-05-8 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 7720 - 7729

50
[ 89043-32-3 ]
[ 1341192-30-0 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 6078 - 6081

51
[ 89043-32-3 ]
[ 14260-64-1 ]
[ 1341192-29-7 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 6078 - 6081

52
[ 89043-32-3 ]
2-[(piperazine-1-yl)carbonyl]-1H-indole [ No CAS ]
[ 1381991-81-6 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 5826 - 5840

53
[ 1419607-71-8 ]
[ 89043-32-3 ]
[ 1419607-69-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 827 - 833

54
C₁₀H₁₆S₂ [ No CAS ]
[ 89043-32-3 ]
tert-butyl[4-[2-(4-methyl-penta-1,3-dienyl)[1,3]dithiane-2-yl]butoxy]diphenylsilane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%		Known alcohol 82 (4.0 g, 36 mmol) was added to a solution of MnO2 (38.5 g, 396 mmol) in 225 mL of anhydrous dichloromethane. The mixture was stirred overnight (approximately 18 h). The MnO2 was filtered off and the dichloromethane concentrated to give the crude corresponding aldehyde. This compound was dissolved in dichloromethane (10 mL) and dried over MgSO4, filtered, and then cannulated into a flask containing 1,3-propanedithiol (3.9 g, 36 mmol), Mg(ClO4)2 (402 mg, 1.80 mmol), conc. sulfuric acid (6 drops) and 57 mL of anhydrous dichloromethane that had been pre-cooled to 0 C. The reaction was allowed to warm to room temperature. After 2 h the reaction mixture was quenched in ice cold 10% KOH (72 mL) and allowed to stir for 15 min. Dichloromethane was added and the organic layer separated. The aqueous layer was then extracted with dichloromethane (3x). The combined organic layers were washed with 10% KOH (1x), H2O (1x), brine (1x), dried over MgSO4, filtered, and concentrated. Purification by silica gel chromatography (5-33% ethyl acetate/hexanes) gave 5.08 g (70% over two steps) of a light yellow oil, the dithiane (TLC Rf = 0.40 (6% ethyl acetate/hexanes)

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 1734 - 1737

55
[ 55687-30-4 ]
[ 89043-32-3 ]
1-(4-[tert-butyl(dimethyl)silyl]oxy}butyl)-7-methoxyquinoxalin-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%		7-Methoxyquinoxalin-2(1H)-one (synthesized with reference to WO2009/1126; 400 mg, 2.27 mmol) was dissolved in N,N-dimethylformamide (8 ml). The solution was cooled in an ice bath, lithium hydride (purity 90%, 26 mg, 2.95 mmol) was then added thereto and the mixture was stirred at room temperature for 40 minutes. The reaction solution was cooled in an ice bath again, (4-bromobutoxy)(tert-butyl)dimethylsilane (synthesized with reference to Journal of Medicinal Chemistry, 2008, vol. 51, No. 18, pages 5690-5701; 580 mg, 2.17 mmol) and sodium iodide (442 mg, 2.95 mmol) were added thereto, and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, washed sequentially with saturated sodium chloride solution (X2), water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to yield 363 mg (44%) of the title compound in the form of a light yellow syrup. 1H-NMR(400MHz,CDCl3)delta:0.05(6H,s), 0.88(9H,s), 1.63-1.69(2H,m), 1.82-1.88(2H,m),3.69(2H,t,J=6.0Hz),3.92(3H,s),4.25(2H,t,J=7.7Hz),6.79(1H,d,J=2.3Hz),6.92(1 H,dd,J=8.9,2.6Hz),7.79(1H,d,J=8.6Hz),8.13(1H,s). MS(ESI)m/z:363(M+H)+.

Reference： [1]Patent: EP2674430,2013,A1 .Location in patent: Paragraph 0087

56
[ 60683-53-6 ]
[ 89043-32-3 ]
[ 1526990-25-9 ]

Yield	Reaction Conditions	Operation in experiment
70%		A frame-dried round bottom flask was charged with a solution of 6 (1.09 g, 5.0 mmol) in anhydrous THF (7 mL) under argon atmosphere. n-BuLi (3.6 mL, 6 mmol, 1.6 M n-hexane solution) was added to the solution prepared above at 0 C and the reaction mixture was stirred for 2 h at room temperature. The mixture was cooled to -80 C and <strong>[89043-32-3](4-bromobutoxy)-tert-butyldimethylsilane</strong> (1.9 g, 5.1 mmol) solution in THF (1 mL) was added via cannula and the mixture was stirred for 48 h. The reaction mixture was worked up by addition of satd aqueous NH4Cl and AcOEt. The mixture was separated and the aqueous layer was extracted with AcOEt. The combined organic layer was washed with water, brine and dried over MgSO4, and concentrated in vacuo. The resulting residue was purified by flash chromatography (hexane/AcOEt=6:1) to afford 1.42 g (70%) of desired tert-butyldimethyl-[4-(1,3,4-trimethoxynaphthalen-2-yl)-butoxy]-silane (12). 1H NMR (400 MHz, CDCl3) delta 0.04 (s, 6H, Si(CH3)2), 0.89 (s, 9H, Si-tert-C(CH3)3), 1.62-1.71 (m, 4H, CH2 2), 2.81 (t, 2H, J=7.3 Hz, CH2), 3.66 (m, 2H, CH2OSi), 3.90 (s, 3H, OCH3), 3.95 (s, 3H, OCH3), 3.99 (s, 3H, OCH3), 7.39 (td, 2H, J=6.0, 2.0 Hz, aryl-H 2), 7.99 (dd, 1H, J=2.0, 7.0 Hz, aryl-H), 8.08 (dd, 1H, J=2.0, 7.0 Hz, aryl-H). 13C NMR (100 MHz, CDCl3) delta -2.9 (CH3), 18.3 (C), 26.0 (CH3), 60.8 (CH3), 62.3 (CH3), 63.1 (CH3), 121.6 (CH), 122.1 (CH), 124.8 (CH), 125.4 (C), 125.5 (CH), 128.0 (C), 128.2 (C), 143.5 (C), 148.5 (C), 150.1 (C). HRMS calcd for C23H36O4Si: 404.2383. Found: 404.2382.

Reference： [1]Tetrahedron,2014,vol. 70,p. 502 - 509

57
[ 1225962-32-2 ]
[ 89043-32-3 ]
[ 1563175-23-4 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 1557 - 1572

58
[ 89043-32-3 ]
[ 185203-71-8 ]
[ 1612780-81-0 ]