324-41-4|2-Bromo-6-fluoronaphthalene| Ambeed

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Quality Control of [ 324-41-4 ] Purity: 98% SDS Specification

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NMR

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Product Details of [ 324-41-4 ]

CAS No. :	324-41-4
Formula :	C₁₀H₆BrF
M.W :	225.06
SMILES Code :	FC1=CC2=CC=C(Br)C=C2C=C1
MDL No. :	MFCD09763683
InChI Key :	CAJAZWLCCNCVEY-UHFFFAOYSA-N
Pubchem ID :	345397

Safety of [ 324-41-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 324-41-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	10
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	1.0
Num. H-bond donors	0.0
Molar Refractivity	51.61
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	0.0 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.51
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	3.4
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	4.16
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	4.45
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	4.06
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.72

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.99
Solubility	0.0228 mg/ml ; 0.000101 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.08
Solubility	0.187 mg/ml ; 0.000833 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-5.21
Solubility	0.00138 mg/ml ; 0.00000615 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	Low
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	Yes
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.26 cm/s

Druglikeness

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

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.41

Application In Synthesis of [ 324-41-4 ]

* 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 [ 324-41-4 ]

[ 324-41-4 ] Synthesis Path-Downstream 1~35

1
[ 85-44-9 ]
[ 324-41-4 ]
[ 3799-80-2 ]

References: [1]Journal of Organic Chemistry,1960,vol. 25,p. 214 - 215.

2
[ 324-41-4 ]
[ 544-92-3 ]
[ 13790-83-5 ]

References: [1]Journal of the American Chemical Society,1967,vol. 89,p. 386 - 390.

3
6-Brom-naphthalin-diazonium-⁽²⁾ [ No CAS ]
[ 324-41-4 ]

References: [1]Journal of the American Chemical Society,1967,vol. 89,p. 386 - 390.
[2]Journal of Organic Chemistry,1960,vol. 25,p. 214 - 215.

4
[ 324-41-4 ]
[ 676-58-4 ]
[ 74-88-4 ]
[ 59080-11-4 ]

References: [1]Journal of the American Chemical Society,1976,vol. 98,p. 1701 - 1711.

6
[ 89531-03-3 ]
[ 324-41-4 ]
(2RS,3SR)-1,2-dimethyl-3-[2-(6-fluoronaphthyl)-3-hydroxy]pyrrolidine hydrochloride [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2000,vol. 8,p. 1925 - 1930.

7
[ 7499-66-3 ]
[ 324-41-4 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine hydrogenfluoride; sodium nitrite; at 85℃; for 4h;	Commercially available 6-bromo-2-aminonaphthalene (100 mg, 0.45 mmol) in 4 mL of HF-pyridine was treated with sodium nitrite (101 mg, 1.35 mmol), aged to a thickly turbid mixture after 2 h, heated m a sealed tube at 85 0C for 2 h, the mixture cooled, and partitioned between chloroform and water. The organic phase was separated and concentrated in vacuo to provide the clean 6-bromo-2- fluoronaphthalene product. EXAMPLE 18 was prepared from this 6-bromo-2-fluoronaphthalene intermediate in a manner similar to EXAMPLE 17 above and illustrated in Scheme 5. The desired product was purified via preparative RPHPLC. 1H NMR (CD3OD, 600 MHz) delta 8.54 (d, 1H), 8 05 (dd, 1H), 7.81 (dd, 1H), 7.66-7.38 (m, 2H), 7.54 (dt, 1H), 7.46-7.44 (m, 2H), 7.24 (dt, 1H), 7 12 (t, 1H), 3.20 (t, 2H), 2.83 (t, 2H); LCMS m/z 338 (M++1).

References: [1]Bioorganic and Medicinal Chemistry,2000,vol. 8,p. 1925 - 1930.
[2]Journal of Organic Chemistry,1960,vol. 25,p. 214 - 215.
[3]Journal of the American Chemical Society,1967,vol. 89,p. 386 - 390.
[4]Patent: WO2006/52555,2006,A2 .Location in patent: Page/Page column 28; 48-49.

8
[ 324-41-4 ]
[ 2543-57-9 ]
(RS)-4-dimethylamino-2-(6-fluoronaphthalen-2-yl)butan-2-ol [ No CAS ]

References: [1]Tetrahedron Asymmetry,2002,vol. 13,p. 1073 - 1081.

9
[ 324-41-4 ]
[ 2543-57-9 ]
(R)-4-dimethylamino-2-(6-fluoronaphthalen-2-yl)butan-2-ol [ No CAS ]
(S)-4-dimethylamino-2-(6-fluoronaphthalen-2-yl)butan-2-ol [ No CAS ]

References: [1]Tetrahedron Asymmetry,2002,vol. 13,p. 1073 - 1081.

10
[ 324-41-4 ]
(R)-1,2-Dimethyl-pyrrolidin-3-one [ No CAS ]
(2R,3S)-3-(6-Fluoro-naphthalen-2-yl)-1,2-dimethyl-pyrrolidin-3-ol [ No CAS ]

References: [1]Tetrahedron Asymmetry,2004,vol. 15,p. 3601 - 3608.
[2]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 3117 - 3126.

11
[ 324-41-4 ]
(S)-1,2-Dimethyl-pyrrolidin-3-one [ No CAS ]
(2S,3R)-3-(6-Fluoro-naphthalen-2-yl)-1,2-dimethyl-pyrrolidin-3-ol [ No CAS ]

References: [1]Tetrahedron Asymmetry,2004,vol. 15,p. 3601 - 3608.
[2]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 3117 - 3126.

12
[ 324-41-4 ]
3-(6-fluoro-naphthalen-2-yl)-1,2-dimethyl-2,5-dihydro-1<i>H</i>-pyrrole [ No CAS ]

References: [1]Tetrahedron Asymmetry,2004,vol. 15,p. 3601 - 3608.

13
[ 324-41-4 ]
3-(6-fluoro-naphthalen-2-yl)-1,2-dimethyl-2,5-dihydro-1<i>H</i>-pyrrole [ No CAS ]

References: [1]Tetrahedron Asymmetry,2004,vol. 15,p. 3601 - 3608.

14
[ 15231-91-1 ]
[ 324-41-4 ]

References: [1]Bioorganic and Medicinal Chemistry,2000,vol. 8,p. 1925 - 1930.
[2]Journal of Organic Chemistry,1960,vol. 25,p. 214 - 215.

15
[ 324-41-4 ]
[ 5043-01-6 ]

References: [1]Journal of the American Chemical Society,1967,vol. 89,p. 386 - 390.

16
[ 324-41-4 ]
[ 5043-00-5 ]

References: [1]Journal of the American Chemical Society,1967,vol. 89,p. 386 - 390.

17
[ 324-41-4 ]
[ 4167-90-2 ]
[ 38659-77-7 ]

References: [1]Journal of Organometallic Chemistry,1972,vol. 42,p. 373 - 390.
[2]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Sn: Org.Verb.2, 1.1.2.15.2, page 359 - 384.

18
[ 5043-01-6 ]
[ 324-41-4 ]

References: [1]Patent: WO2011/61168,2011,A1 .

19
[ 87700-58-1 ]
[ 324-41-4 ]

Yield	Reaction Conditions	Operation in experiment
40%	With 2,2'-azobis(isobutyronitrile); Bromotrichloromethane; 2-mercaptopyridine-1-oxide sodium salt; at 100℃; for 0.75h;	Step 2: 2-bromo-6-fluoronaphthalene (6b) 6-fluoro-2-naphthoyl chloride (472 mg, 2.097 mmol, 39.9 % yield) was combined with AIBN (173 mg, 1.052 mmol) in CBrCI3 (10 ml_). That mixture was added slowly to a mixture of 2- Mercaptopyridine N-oxide sodium salt (981 mg, 6.58 mmol) and CBrCI3 (10 mL) at 100 C over 30 min. After the completion of addition, the mixture was stirred for another 15 min, then cooled. The mixture was quenched with H20 and extracted with EtOAc two times, dried over magnesium sulfate, filtered, concentrated. The residue was purified via Biotage (0-5% EtOAc/heptane; SNAP25 column) giving 6b (472 mg, 40%) as white solid. 1H NMR (400 MHz, MeOD) delta ppm 7.34 (td, J=8.84, 2.59 Hz, 1 H) 7.49 - 7.57 (m, 1 H) 7.60 (ddd, J=8.78, 1.96, 0.69 Hz, 1 H) 7.77 (d, J=8.84 Hz, 1 H) 7.87 (dd, J=9.09, 5.56 Hz, 1 H) 8.09 (d, J=1.58 Hz, 1 H).

References: [1]Patent: WO2011/61168,2011,A1 .Location in patent: Page/Page column 53.

20
[ 324-41-4 ]
[ 1332333-61-5 ]
[ 1332333-14-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In water; at 20 - 100℃; for 1h;Inert atmosphere; Capped vial; Microwave irradiation;	Example 2075-[(35)-l-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-4-[2-fluoro-4-(6-fluoro-2- naphthalenyl)phenyl]-2,4-dihydro-3H-l,2,4-triazol-3-onea) Into a 5 mL microwaveable vial was placed 4-(4-bromo-2-fluorophenyl)-5-[(35)-l- (cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-2,4-dihydro-3H-l,2,4-triazol-3-one (0.244 mmol), bis(pinacolato)diboron (0.244 mmol), potassium acetate (0.977 mmol), dichloro [ 1 , 1 ' -bis(diphenylphosphino)ferrocene]palladium(II)-dichloromethane adduct (0.024 mmol), and 1,4-dioxane (2 mL). The vial was capped and the contents were purged with nitrogen. The solution stirred at 100 C for 16 h. LCMS analysis displayed boronic ester intermediate present (boronic ester cleavage to acid also observed on LCMS) as well as a small amount of bromide starting material. The reaction was cooled to room temperature. Added to the vial was <strong>[324-41-4]2-bromo-6-fluoronaphthalene</strong> (0.244 mmol) and 2M aq potassium carbonate (1 mL). The vial was capped, purged with nitrogen, and stirred at 100 C for 1 h. The solution was cooled to room temperature, whereby the dioxane layer separated from the aqueous layer. The dioxane layer was removed via pipette and was passed through a plug of celite and sodium sulfate. The plug was washed with dioxane (2 mL). All dioxane filtrates were combined and concentrated in vacuo. Reverse phase HPLC (30-80% acetonitrile/water + 0.1% NH4OH) was utilized in purifying the title compound (21 mg, 17%). MS(ES)+ m/e 475.1 [M+H]+.

References: [1]Patent: WO2011/103546,2011,A1 .Location in patent: Page/Page column 209.

21
[ 324-41-4 ]
[ 73183-34-3 ]
[ 1308669-74-0 ]

Yield	Reaction Conditions	Operation in experiment
54%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl-formamide; at 90℃;	General procedure: Aryl halide (1 equiv), bis-pinacolato-diboron (1.5-3 equiv), Pd(dppf)Cl2 (0.05-0.1 equiv), and KOAc (3-6 eq.) were suspended in DMF (2-6 mL). The mixture was then heated at 90 C for 2-6 h, cooled to rt, diluted with H2O (10 mL) and extracted with EtOAc (3 × 5 mL). The organic layer was dried (MgSO4) and the solvent removed in vacuo. The residue was purified by chromatography using a stepped gradient of 0-10% EtOAc in heptane to yield the desired boronic ester.

References: [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 1284 - 1304.

22
[ 324-41-4 ]
[ 1426083-09-1 ]

References: [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 1284 - 1304.

23
[ 324-41-4 ]
(2-{4-[5-(6-fluoro-naphthalen-2-yl)-4-pyridin-4-yl-1H-imidazol-2-yl]-phenoxy}-ethyl)-dimethyl-amine hydrochloride [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 1284 - 1304.

24
[ 324-41-4 ]
4-cyclopropyl-9-(piperazin-1-ylsulfonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-3-one hydrochloride [ No CAS ]
4-cyclopropyl-9-((4-(6-fluoronaphthalen-2-yl)piperazin-1-yl)sulfonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-3-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
15%	With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate; In 1,4-dioxane; toluene; at 100℃; for 48h;Sealed tube; Microwave irradiation;	In a sealed 5 mL microwave vial purged with nitrogen, a mixture of 4-cyclopropyl-9-(piperazin- 1 -ylsulfonyl)- 1 -oxa-4,9-diazaspiro [5.5 ]undecan-3 -one hydrochloride (177 mg, 0.448 mmol), <strong>[324-41-4]2-bromo-6-fluoronaphthalene</strong> (101 mg, 0.448 mmol), sodium tert-butoxide (60.3 mg, 0.627 mmol), palladium(II) acetate (5.03 mg, 0.022 mmol),1,4-dioxane (2 mL), and tri-tert-butylphosphine (1M in toluene, 0.025 mL, 0.025 mmol) was stirred for 48 h at 100 C. LCMS analysis was used to monitor the reaction?s progress. It was determined that after 48 h the reaction did not appear to be progress beyond 50% completion. The solution was cooled to room temperature and filtered through a pad of Celite, which was then washed with dioxane (2 mL). The filtrate was concentrated in vacuo and purified byreverse phase HPLC (35-65% acetonitrile w/ 0.1% TFA/water w/ 0.1% TFA). The recovered material was taken up in 1:1 dichloromethane : acetonitrile (2 mL total) and passed throughPL-HCO3 macroporous solid phase extraction plug (100 mg, 0.18 mmol) to neutralize the TFA salt. The plug was washed with a fresh 1:1 dichloromethane : acetonitrile solution (2 mL total). The combined organic filtrate was concentrated in vacuo to afford the titlecompound (33 mg, 15%). MS(ES)+ mle 503.0 [M+H].

References: [1]Patent: WO2013/177253,2013,A2 .Location in patent: Page/Page column 69.

25
[ 324-41-4 ]
[ 1429790-73-7 ]
[ 73183-34-3 ]
[ 1534371-85-1 ]

Yield	Reaction Conditions	Operation in experiment
54%		a) A 5 mL microwave vial was charged with 9-[(4-bromo-2,6-difluorophenyl)methyl]-4- cyclopropyl-l-oxa-4,9-diazaspiro[5.5]undecan-3-one (90 mg, 0.217 mmol), bis(pinacolato)diboron (60 mg, 0.236 mmol), potassium acetate (85 mg, 0.867 mmol), Iota,Gamma- bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (20 mg, 0.024 mmol), and 1,4-dioxane (2 mL). The vial was capped, the contents were purged with nitrogen, and the solution was stirred at 100 C for 2 h. The reaction was cooled to room temperature and <strong>[324-41-4]2-bromo-6-fluoronaphthalene</strong> (50 mg, 0.222 mmol) was added followed by 2M aq. potassium carbonate (1 mL). The vial was capped, purged with nitrogen, and stirred at 100 C for 1 h. The solution was set aside to cool to room temperature and to allow the phases to separate. The dioxane layer was removed and passed through a plug of Celite and sodium sulfate. The plug was washed with dioxane (2 mL). The filtrate was concentrated in vacuo. This was purified by reverse phase HPLC (30-90% acetonitrile /water w/ 0.1% NH4OH) then by reverse phase HPLC (25-55% acetonitrile w/ 0.1% TF A/water w/ 0.1% TFA). The desired fractions were combined and concentrated in vacuo. The recovered material was taken up in 1 : 1 dichloromethane: acetonitrile (2 mL) and passed through a macroporous solid phase extraction plug (PL-HCO3, 100 mg, 0.18 mmol) to neutralize the TFA salt. The column was washed with a fresh solution of 1 : 1 dichloromethane: acetonitrile (2 mL). All of the organic filtrate was concentrated to dryness to afford the title compound (57 mg, 54%). MS (ES)+ m/e 481.1 [M+H]+.

References: [1]Patent: WO2014/8223,2014,A2 .Location in patent: Page/Page column 101.

26
[ 61676-62-8 ]
[ 324-41-4 ]
[ 1308669-74-0 ]

Yield	Reaction Conditions	Operation in experiment
67%		As follows: the formula (6) Compound 9 (1.0g, 4.44mmol) was added to a single neck flask, pumping Vacuum / nitrogen filling repeated five times, followed by the addition of anhydrous THF30mL, isopropanol / liquid nitrogen after freezing to 78 C In30min slowly added dropwise 2.5M nbutyllithium(1.86mL, 4.66mmol), 1h, add isopropanol Pinacol borate (1.13mL,5.55mmol). Reaction 2h, slowly raising the temperature to room temperature, the reaction 8h, After the reaction was added towater, the product was extracted with methylene chloride, the organic phase was dried over anhydrous magnesium sulfate,separated to The solvent, separated and purified by silica gel column chromatography to give a white solid (6) compound 10co 0.8g, yield 67%.
65%		A solution of n-BuLi in n-hexane (2.5M, 1.86mL, 4.67mmol) was added dropwise to a solution of <strong>[324-41-4]2-bromo-6-fluoronaphthalene</strong> (1.00g, 4.44mmol) in anhydrous THF (20mL) under nitrogen at-78C. After the reaction was kept at-78C for 1h, isopropoxyboronic acid pinacol ester (1.12mL, 5.56mmol) was added. The mixture was left to warm up to room temperature overnight. Then it was evaporated under vacuum. The residue was treated with water and extracted with CH2Cl2. The organic phase was further washed with water and brine, and dried over MgSO4. Upon concentration under vacuum, the crude product was purified by column chromatography on silica gel using CH2Cl2 as the eluent to obtain a white solid (0.785g, 65%). 1H NMR (300MHz, DMSO): delta 8.25 (s, 1H), 8.09-8.14 (m, 1H), 7.88 (d, J=8.28Hz, 1H), 7.68-7.75 (m, 2H), 7.40-7.46 (m, 1H), 1.31 (s, 12H).

References: [1]Patent: CN103360397,2016,B .Location in patent: Paragraph 0044-0046.
[2]Dyes and Pigments,2014,vol. 101,p. 51 - 57.

27
[ 324-41-4 ]
1-[4-(6-fluoro-naphthalen-2-yl)-piperazin-1-yl]-2-[4-(4-nitro-3-trifluoromethyl-henylamino)-cyclohexyloxy]-ethanethione [ No CAS ]

References: [1]Patent: US2014/142114,2014,A1 .

28
[ 324-41-4 ]
1-[4-(6-fluoronaphthalen-2-yl)piperazin-1-yl]-2-[(4-[[4-nitro-3-(trifluoromethyl)phenyl]amino]cyclohexyl)oxy]ethan-1-one [ No CAS ]

References: [1]Patent: US2014/142114,2014,A1 .

29
[ 110-85-0 ]
[ 324-41-4 ]
1-(6-fluoronaphthalen-2-yl)piperazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; In toluene; at 70℃;Inert atmosphere;	0435] To a solution of <strong>[324-41-4]2-bromo-6-fluoronaphthalene</strong> (1 g, 4.44 mmol) in 30 ml of toluene was added sodium tert-butoxide (0.854 g, 8.89 mmol, 2.0 eq), piperazine (0.764 g, 8.87 mmol, 2.0 eq), BINAP (28 mg, 0.045 mmol, 1 mol %) and Pd2(dba)3.CHCl3 (92 mg, 0.089 mmol, 2 mol %) at 70 C. in an oil bath under an inert atmosphere of nitrogen. The resulting solution was stirred overnight and then concentrated under vacuum. The crude material was purified by silica gel chromatography using 10-20% methanol in dichloromethane to elute. The product-containing fractions were combined and concentrated under vacuum to afford 1-(6-fluoronaphthalen-2-yl)piperazine as a light yellow solid (0.75 g, 73%). (ES, m/z): [M+H]+ 231.1; 1H NMR (300 MHz, CDCl3): delta 7.67-7.73 (m, 2H), 7.29-7.38 (m, 2H), 7.18-7.23 (m, 1H), 7.14 (d, J=1.8 Hz, 1H), 3.24 (dd, J=3.6, 3.9 Hz, 4H), 3.12 (dd, J=3.6, 3.9 Hz, 4H).

References: [1]Patent: US2014/142114,2014,A1 .Location in patent: Paragraph 0434; 0435.

30
[ 324-41-4 ]
C₁₄H₁₃FO₂ [ No CAS ]