[ CAS No. 460-00-4 ] {[proInfo.proName]}

Name: 460-00-4|1-Bromo-4-fluorobenzene|95%
Brand: Ambeed
SKU: A486887
Price: 5.0 USD
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Quality Control of [ 460-00-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 460-00-4 ]

Product Details of [ 460-00-4 ]

CAS No. :	460-00-4	MDL No. :	MFCD00000342
Formula :	C₆H₄BrF	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	AITNMTXHTIIIBB-UHFFFAOYSA-N
M.W :	175.00	Pubchem ID :	9993
Synonyms :

Calculated chemistry of [ 460-00-4 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	34.1
TPSA :	0.0 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.18 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.09
Log Po/w (XLOGP3) :	3.08
Log Po/w (WLOGP) :	3.01
Log Po/w (MLOGP) :	3.48
Log Po/w (SILICOS-IT) :	3.0
Consensus Log Po/w :	2.93

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.42
Solubility :	0.0665 mg/ml ; 0.00038 mol/l
Class :	Soluble
Log S (Ali) :	-2.75
Solubility :	0.313 mg/ml ; 0.00179 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.52
Solubility :	0.0522 mg/ml ; 0.000299 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.29

Safety of [ 460-00-4 ]

Signal Word:	Danger	Class:	3
Precautionary Statements:	P261-P305+P351+P338	UN#:	1993
Hazard Statements:	H225-H315-H319-H332-H335	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 460-00-4 ]

* 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 [ 460-00-4 ]

[ 460-00-4 ] Synthesis Path-Downstream 1~88

1
[ 460-00-4 ]
[ 1435-53-6 ]

Reference： [1]Journal of the Indian Chemical Society,1944,vol. 21,p. 112,114

2
[ 462-06-6 ]
[ 1072-85-1 ]
[ 1435-53-6 ]
[ 3925-78-8 ]
[ 359-90-0 ]
[ 460-00-4 ]

Reference： [1]Journal of Fluorine Chemistry,1990,vol. 46,p. 393 - 406

3
[ 462-06-6 ]
[ 1072-85-1 ]
[ 1435-53-6 ]
[ 359-90-0 ]
[ 460-00-4 ]

Reference： [1]Journal of Fluorine Chemistry,1990,vol. 46,p. 393 - 406

4
[ 2369-18-8 ]
[ 460-00-4 ]
[ 101419-76-5 ]

Reference： [1]Journal of Organic Chemistry,1986,vol. 51,p. 2021 - 2023

5
[ 19230-28-5 ]
[ 124-38-9 ]
[ 460-00-4 ]
4,4''-difluoro-[1,1':3',1''-terphenyl]-2'-carboxylic acid [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1994,vol. 116,p. 5959 - 5960

6
[ 2716-23-6 ]
[ 460-00-4 ]
[ 53272-74-5 ]

Reference： [1]Journal of the American Chemical Society,1974,vol. 96,p. 5166 - 5175

7
[ 7726-95-6 ]
[ 460-00-4 ]
iron-powder [ No CAS ]
[ 2369-37-1 ]
[ 1435-53-6 ]

Reference： [1]Journal of the Indian Chemical Society,1944,vol. 21,p. 112,114

8
[ 462-06-6 ]
1-1.3 mol bromine [ No CAS ]
iron-turnings [ No CAS ]
[ 2369-37-1 ]
[ 1435-53-6 ]
[ 460-00-4 ]

Reference： [1]Journal of the American Chemical Society,1941,vol. 63,p. 602,603

9
[ 69814-56-8 ]
[ 460-00-4 ]
C₁₂H₁₃FO₂ [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2002,p. 151 - 156

10
[ 28741-08-4 ]
[ 460-00-4 ]
[ 28593-20-6 ]

Reference： [1]Tetrahedron,2004,vol. 60,p. 3813 - 3818

11
[ 3054-95-3 ]
[ 460-00-4 ]
[ 7116-38-3 ]
[ 106485-14-7 ]

Reference： [1]Tetrahedron,2004,vol. 60,p. 11533 - 11540

12
[ 18471-40-4 ]
[ 460-00-4 ]
1-benzyl-3-(4-fluorophenylamino)pyrrolidine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 8893 - 8902

13
[ 144432-85-9 ]
[ 460-00-4 ]
3-chloro-4,4'-difluorobiphenyl [ No CAS ]

Reference： [1]Chemistry - A European Journal,2006,vol. 12,p. 4407 - 4416

14
[ 673-40-5 ]
[ 174899-83-3 ]
C₈H₄NS₂O₄F₆Br [ No CAS ]
C₈H₄NO₄S₂F₆Br [ No CAS ]
[ 460-00-4 ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 6758 - 6762

15
[ 426-65-3 ]
[ 460-00-4 ]
[ 80180-01-4 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of 1-bromo-4-fluorobenzene (16.5 mL, 0.15 mol) in anhydrous THF (200 mL) at -78 C, 2,2,3,3,3-pentafluoropropionic acid ethyl ether (14.4 g, 75 mmol) was slowly added. After stirring for 4 h at -78 C, ethyl ether (200 mL) and sat. sol. of NH4Cl (100 mL) were added. The resulting mixture was placed in a sep. funnel, shaken and the organic phase separated. After washing with brine, the solution was dried over magnesium sulfate. The solution was concentrated in a rotary vapor and the residue was purified by distillation to give 2,2,3,3,3-pentafluoro-1-(4-fluorophenyl)propan-1-one.

Reference： [1]Chemistry - A European Journal,2015,vol. 21,p. 18944 - 18948
[2]Patent: WO2006/102535,2006,A2 .Location in patent: Page/Page column 79

16
[ 82104-74-3 ]
[ 142-82-5 ]
[ 352-13-6 ]
[ 460-00-4 ]
[ 207680-98-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tetrahydroborate; magnesium; In tetrahydrofuran; ethanol; water; ethyl acetate;	Example 1 (4-Cyano-2-hydroxymethylphenyl)(4-fluorophenyl)methanol A solution of 4-fluorophenylmagnesium bromide, prepared from 4-fluorobromobenzene (605 g, 3.45 mole) and magnesium turnings (107 g, 4.4 mole) in dry THF (1200 mL), is added dropwise to a suspension of 5-cyanophthalid (500 g, 3.14 mole) in dry THF (3000 mL). The temperature is kept below 5° C. After the addition is complete, the reaction mixture is stirred the night over at room temperature. Ethanol (4500 mL) is added to the reaction mixture and NaBH4 (238 g, 6.30 mole) is added to the mixture in portions of 50 grams and is stirred the night over at room temperature. About 2/3 of the solvents is removed in vacuo and water (4000 mL) is added to the reaction mixture. The resulting solution is extracted with EtOAc (2*500 mL). Evaporation of the solvents leaves a crude title compound (780 g) as an oil which is deemed pure enough for further reaction. A pure sample is obtained after column chromatography on silica gel using EtOAc/n-Heptane (1/1) as eluent. The title compound is obtained as crystals after evaporation of the eluent. DSC onset: 116.5° C. 1H NMR (DMSO-db, 500 MHz): 4.42 (1H, dd J=13 Hz, J=5 Hz), 4.53 (1H, dd J=13 Hz, J=5 Hz), 5.45 (1H, t J=5 Hz), 5.98 (1H, d J=3 Hz), 6.14 (1H, d J=3 Hz), 7.15 (2H, J=10 Hz), 7.35 (2H, m), 7.74 (1H, d J=8.5 Hz), 7.77 (1H, d J=8.5 Hz), 7.83 (1H, s). Anal. calcd. for C15H12N1F1O2; C, 70.02; H, 4.71; N, 5.45. Found C, 70.01; H, 4.71; N, 5.51.

Reference： [1]Patent: US6291689,2001,B1

17
[ 1003-31-2 ]
[ 460-00-4 ]
[ 1044231-51-7 ]

Reference： [1]Green Chemistry,2009,vol. 11,p. 425 - 432
[2]Advanced Synthesis and Catalysis,2007,vol. 349,p. 2507 - 2516

18
[ 69861-71-8 ]
[ 460-00-4 ]
[ 165901-75-7 ]

Reference： [1]Organometallics,1995,vol. 14,p. 3030 - 3039

19
[ 82104-74-3 ]
[ 7439-95-4 ]
[ 460-00-4 ]
[ 64169-67-1 ]

Yield	Reaction Conditions	Operation in experiment
86%		A solution of 4-fluorophenyl magnesium bromide prepared from 153.33g 4-fluoro bromobenzene (0.876 moles), 25.33g magnesium turnings (1.055 moles) and 0.05g iodine in dry 300ml tetrahydrofuran, is added to a suspension of 100g 5-cyanophthalide (0.628 moles) in 1000ml methylene dichloride at-6 to-2 C and worked up according to the method of Example 1, resulting in a thick semi-solid. This is triturated with 500ml of isopropyl alcohol (IPA) and cooled to0-5 C to provide 5-cyano-1- (4-fluorophenyl)-1, 3-dihydroisobenzofuran (2b) as a solid. This solid is filtered and washed with cold 50ml of IPA. Yield: 130-140g HPLC purity: 99.32percent
		A solution of 4-fluorophenyl magnesium bromide prepared from 153.33g 4-fluoro bromobenzene (0.876 moles), 25.33g magnesium turnings (1.055 moles) and 0.05g iodine in dry 300ml tetrahydrofuran, is added to a suspension of 100g 5-cyanophthalide (0.628 moles) in 1000 ml toluene at-6to-2 C and worked-up as explained in Example 4 to provide a thick semi-solid. This is triturated with 500mi of isopropyl alcohol (IPA) and cooled to0-5 C to provide 2b as a solid. The solid is filtered and washed with 50ml of cold IPA. Dry weight :105-110g Purity by HPLC: 97.5percent

Reference： [1]Patent: WO2004/20425,2004,A1 .Location in patent: Page 11
[2]Patent: WO2004/20425,2004,A1 .Location in patent: Page 13-14

20
[ 82104-74-3 ]
[ 7439-95-4 ]
[ 460-00-4 ]
[ 207680-98-6 ]

Yield	Reaction Conditions	Operation in experiment
		A solution of 4-fluorophenyl magnesium bromide prepared from 153.33g 4-fluoro bromobenzene (0.876 moles), 25.33g magnesium turnings (1.055 moles) and 0.05g iodine in dry300moi tetrahydrofuran, is added to a suspension of 100g 5-cyanophthalide (0.628 moles) in1000ml methylene dichloride at-6to-2 C. After the reaction is completed, the reaction mass is quenched with100ml 20percent aqueous ammonium chloride solution. The organic layer is separated and diluted with100ml of methanol. Slowly, 12g of sodium borohydride (0.324moles) added over a period of one hour at below25 C, and the same temperature is maintained for 4-6 hours. The mixture is then cooled to 5-10 C, maintained for 2 hours and then the precipitated solid is filtered. The solid is washed with cold water and dried under vacuum below40 C to provide pure4-cyano-2-hydroxymethylphenyl- (4-fluorophenyl) methanol (5b). Yield: 115-120g HPLC purity: 99.2percent

Reference： [1]Patent: WO2004/20425,2004,A1 .Location in patent: Page 12

21
[ 7560-83-0 ]
[ 3375-31-3 ]
[ 292638-85-8 ]
[ 460-00-4 ]
[ 96426-60-7 ]

Yield	Reaction Conditions	Operation in experiment
91%	With tetraethylammonium chloride; In ISOPROPYLAMIDE;	Example 11A (E)-methyl 3-(4-fluorophenyl)acrylate A mixture of 1-bromo-4-fluorobenzene (10 g, 57 mmol), methyl acrylate (4.5 g, 52 mmol), tetraethylammonium chloride (8.6 g, 52 mmol), N-cyclohexyl-N-methylcyclohexanamine (15 g, 78 mmol), and palladium (II) acetate (0.35 g, 1.6 mmol) in dimethylacetamide (200 mL) was heated to 100 C. under an argon atmosphere. The reaction was allowed to proceed until the aryl halide was consumed. The reaction mixture was then cooled to room temperature, diluted with Et2O, and washed three times with water. The separated organic phase was dried over MgSO4 and concentrated in vacuo. The crude product was purified by flash column chromatography on silica gel eluding with EtOAc/hexanes to afford 8.5 g (91% yield) of the title compound.

Reference： [1]Patent: US2009/176883,2009,A1

22
[ 13679-74-8 ]
[ 460-00-4 ]
[ 1160585-60-3 ]

Reference： [1]Tetrahedron Letters,2009,vol. 50,p. 2778 - 2781

23
[ 460-00-4 ]
[ 6332-83-8 ]
[ 3801-53-4 ]

Reference： [1]Organic Letters,2009,vol. 11,p. 2575 - 2578

24
[ 1198-30-7 ]
[ 460-00-4 ]
[ 1177408-18-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 4441 - 4447

25
[ 53199-31-8 ]
[ 460-00-4 ]
[ 1204481-90-2 ]

Reference： [1]Journal of the American Chemical Society,2010,vol. 132,p. 1243 - 1245

26
[ 1003-09-4 ]
[ 460-00-4 ]
[ 58861-48-6 ]

Yield	Reaction Conditions	Operation in experiment
91.3%		Under nitrogen, a magnesium shoulder (11. lg, 0.457 mol), a solvent tetrahydrofuran (140 ml), a small amount of p-fluorobromobenzene (10 g, 0.057 mol), and an initiator iodine (0.1 g) were added to the 500 ml reaction flask. , until the color fades, when the determination is triggered, the temperature is controlled at 36-40 C, and parafluorobromobenzene 69.9 g, 0.4 mo 1) is added dropwise within 4 h, and the GC is controlled. After the reaction is completed,Keep warm at 40 C and stop stirring.A 1000 ml reaction flask was taken, and 2-bromothiophene (74.5 g, 0.457 mol) and solvent tetrahydrofuran (150 ml) were added under nitrogen atmosphere, and the mixture was replaced with nitrogen three times. The catalyst DPPE.NIC12 (0.48 g, 0.0009 mol) was added (after milling, 120 mesh) Between the 260 mesh screen, the particle size is 57-125mupi), the temperature is controlled at 20-25 C, the Grignard reagent prepared above is added dropwise, and the addition is completed in 5 hours, and the GC is controlled. After completion of the reaction, it was quenched with 5% EtOAc (EtOAc)EtOAc. Below 60 C, it was evaporated to dryness under reduced pressure and recrystallized from methanol: water = 2:1. After drying, a white solid was obtained: 74.2 g, the reaction yield was 91.3%, and the HPLC purity was 99.5 %.
87.6%		4.1 Format response In a 1000 ml four-necked flask, Nitrogen protection, First put the magnesium tablets 14 grams (0.58mol), THF 80 g, 2-bromothiophene 1 g, stirred. About 30 deg C, Began to trigger the reaction (with bubbles, the temperature naturally rose to 35-45 deg C). Cooling with cold water to 30 deg C, A mixture of 81 g (0.5 mol) of 2-bromothiophene and 1,16 g of THF was added dropwise, About two hours dripping finished. The dropping process controls the temperature at about 30 C. Drop finished, The reaction was carried out at 30 C for 30-60 minutes, sampling, Raw 2-bromothiophene <0.5% qualified. End.seal, stand-by.;_4.2 Coupling reaction In another 1000 ml four-necked flask. Nitrogen protection, Put THF 40 g, 93 g (0.53 mol) of fluorobromobenzene. Stir well. A solution of 5.5 g (0.005 mol) of tetrakis (triphenylphosphine) Heating up to 60 deg C, Start to add step on the format of liquid (just start dripping more obvious) control temperature of about 70-80 deg C drop. About 1 hour dripping end. 80 deg C reflux insulation reaction 5 hours. sampling, The raw material <0.5% is the reaction end point. End the reaction.;_4.3 hydrolysis The coupling solution was cooled to 50-60 C, In a 2000 ml hydrolyzate bottle, Add 250 ml of water. The coupling droplets are added to the water, To carry out hydrolysis. Control temperature <40 deg C. 20% sulfuric acid adjusted to pH 2 or so. Add activated carbon 5 grams decolorization adsorption impurities, filter. The filtrate is layered. The lower layer of organic layer was transferred to a 1000 ml distillation flask. The THF was recovered by distillation under reduced pressure at atmospheric pressure. To obtain about 85 g of crude 2- (4-fluorophenyl) thiophene, Add 90% methanol water 240 grams, Heating 60 all dissolved, 60 C for 30 minutes, Slowly cool to -10 deg C, Crystallization for two hours. Filter, Drained. Placed in a vacuum oven. 30-40 deg C under vacuum drying. Had a fine 78 grams. The content of GC 99.5% was 87.6%.
75%		26 g (1.08 mol) of magnesium (Mg) and 400 g of dry THF (tetrahydrofuran) were added to the reaction flask,Then add 1 g of 1,2-dibromoethane,Access to nitrogen protection to the system to achieve anaerobic state,And slowly stirring.175 g (1 mol)Fluorobromobenzene (IM 5) was dissolved in 300 g of THF,Dropping about 1/15 to the reaction flask,With the trigger trigger format,Exothermic and produce a lot of gas,The reaction was continued with the addition of a solution of p-fluorobromobenzene / THF.The dropping speed was controlled so that the reaction was semi-reflowed.Not too fast (severe reaction),It can not be too slow (to avoid the reaction to stop) After the drop is completed,Continue to react for about 1.5 h.After completion of the Grignard reaction,Cooled to below 25 C.Remove the remaining magnesium scrap (avoid 2-bromothiophene after formattingInto the thiophene impurities).Transfer the format reagent to a constant pressure drop funnel.160 g (0.98 mol) of 2-bromothiophene (IM 2) and 3 g of catalyst (Ni (dppp) 2Cl2)300 g THF was added to another reaction flask,Ice bath cooling at 10 C,Add the Grignard reagent.Attention to control the drop rate.Keep the temperature below 25 C.After dripping,An additional 3 g of catalyst was added to the reaction flask in portions.After the addition of the catalyst will also reflect the heat (the amount may make the reaction to reflux state).Add the catalyst after stirring for about 0.5h.The temperature was raised to 75 C and the reaction was refluxed overnight.HPLC for controlled reaction.Reaction is completed,Cooling the reaction solution to below 25 C,The reaction solution was slowly poured into a 2 L ice saturated aqueous ammonium chloride solution,Cooling conditions and with 1N dilute hydrochloric acid to adjust the PH value of 2-3,Separate the organic layer,The aqueous layer was extracted with 200 g of x2 ethyl acetate,Combined organic layer,Saturated brine washing,Dried over anhydrous sodium sulfate.filter,Concentrated dry solvent,The product was distilled off under reduced pressure IM3. The temperature was 110-120 C,The vacuum of the pump is 5 mmHg below the vacuum. White solid IM3 129g,Yield: 75%.

Example 8; 2(4-Fluorophenyl)-5,5-iodo-2-methylbenzyl)thiophene The following reactions were carried out under an argon atmosphere.Step A: 4-Fluoro-phenylmagnesium bromide2-Me-THF (80 ml, 0.1 L/mole) was added to Mg (19.44 g, 0.8 mol) and the resulting mixture was stirred slowly. 1-Bromo-4-fluoro-benzene (142.8 g, 0.816 mole) was dissolved in 2-Me-THF (200 ml, 0.25 L/mole) and 25 ml of this solution was added to the Mg mixture. The resulting mixture was heated to about 43 C., the remaining 1-bromo-4-fluorobenzene solution was added over about 40 minutes, while maintaining the mixture at reflux temperature. The addition funnel used to add the 1-bromo-4-fluorobenzene was rinsed with 2-methyl-THF (40 mL) and the rinse was added. The resulting mixture was stirred at 90 C. for 1 hour, then cooled to 20 C. to yield a brown-green solution containing 4-fluoro-phenylmagnesium bromide.Step B: 2-(4-Fluorophenyl)thiophene2-Bromothiophene (130.4 g, 0.8 mol) was dissolved in 2-Me-THF (240 ml, 0.3 L/mole) and the resulting mixture cooled to 2 C. NiCl2(dppe) (2.11 g, 4.0 mmol) was added followed by addition, over about 40 min. at 30 C., of the 4-fluoro-phenylmagnesium bromide solution prepared as in STEP A above to yield a dark red solution. The solution was then stirred at 22 C. for 1.5 hrs. A solution of acetic acid (91.7 ml, 1.6 mol) in water (240 ml, 0.3 L/mol) was then added and the resulting mixture stirred strongly for 15 min. The resulting layers were separated, the organic layer was washed with water (80 ml, 0.1 L/mol), then concentrated in vacuo at 75 C. to yield 2-(4-fluorophenyl)thiophene as a brown oil.

Reference： [1]Patent: CN108658929,2018,A .Location in patent: Page/Page column 4-9
[2]Patent: CN106167480,2016,A .Location in patent: Paragraph 0016; 0030-0065
[3]Patent: CN104418834,2017,B .Location in patent: Paragraph 0012-0016
[4]Patent: US2010/99883,2010,A1 .Location in patent: Page/Page column 40

27
[ 1158098-73-7 ]
[ 460-00-4 ]
[ 1211284-05-7 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 1116 - 1119

28
[ 460-00-4 ]
[ 2942-06-5 ]
6-nitro-2-(4'-fluorophenyl)-1,3-benzothiazole [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 7090 - 7102

29
[ 460-00-4 ]
[ 336191-17-4 ]
[ 1246507-92-5 ]

Yield	Reaction Conditions	Operation in experiment
28%	With sodium t-butanolate;palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 120℃; for 12h;Inert atmosphere;	Step 1: tert-Butyl 8-(4-fluorophenyl)-2,8-diazaspiro[4.5]decane-2-carboxylate Sodium t-butylate (6.24 mmol, 3.0 eq.) was added to a stirred solution of <strong>[336191-17-4]ter<strong>[336191-17-4]t-butyl 2,8-diazaspiro[4.5]decane-2-carboxylate</strong></strong> (2.08 mmol, 1.0 eq.) and 1-bromo-4-fluorobenzene (2.08 mmol, 1.0 eq.) in toluene (15 ml) and the reaction mixture was degassed with N2. BINAP (0.12 mmol, 0.06 eq.) and Pd(OAc)2 (0.04 mmol, 0.02 eq.) were added and the reaction mixture obtained was heated at 120 C. for 12 h. The reaction mixture was filtered over Celite and the filtrate was concentrated in vacuo in order to obtain the crude product, which was purified by column chromatography (silica gel, 12% ethyl acetate in hexane), so that the desired product was achieved. Yield: 28%

Reference： [1]Patent: US2010/249095,2010,A1 .Location in patent: Page/Page column 123

30
[ 19070-16-7 ]
[ 82104-74-3 ]
[ 460-00-4 ]
[ 103146-25-4 ]

Yield	Reaction Conditions	Operation in experiment
		A solution of 4-fluorophenyl magnesium bromide (prepared from 153.3g 4- flouro bromobenzene, 25.3g magnesium turnings and Iodine (0.05gm) in dry 300ml tetrahydrofuran), was added to a suspension of lOOg 5-cyanophthalide in 900ml dichloromethane at -4 to -2°C. After the completion of the reaction a solution of 3- (N,N-dimethylamino)propyl magnesium chloride in toluene/THF mixture [generated in situ by reacting 175g 3-(N,N-dimethylamino)propyl chloride in 350ml toluene with 41.6gm magnesium turnings, 6.0 gin 4-bromofluorobenzene and Iodine in dry tetrahydrofuran] was added between 0 to -50C. The reaction mass was stirred for 3-4 hours. After completion of the reaction, the reaction mass was quenched with 20percent aqueous ammonium chloride solution. The organic layer was separated and washed with water. Organic layer was then extracted with 20percent acetic acid. The aqueous acid extract was cooled and pH was adjusted to 8.5 to 9.0 using liquor ammonia, and extracted with toluene 3 x 600ml. The toluene layer was washed with water, dried and then treated with carbon. Reaction mixture was filtered and subjected to salt formation to get Diol acid addition salts.

Reference： [1]Patent: WO2006/106531,2006,A1 .Location in patent: Page/Page column 11

31
[ 1569-16-0 ]
[ 460-00-4 ]
[ 1256347-61-1 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 5359 - 5361

32
[ 5720-05-8 ]
[ 460-00-4 ]
[ 613-33-2 ]
[ 72093-43-7 ]

Reference： [1]Organometallics,2010,vol. 29,p. 6343 - 6349

33
[ 460-00-4 ]
[ 345-90-4 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 98 - 101

34
[ 18156-74-6 ]
[ 460-00-4 ]
[ 420-56-4 ]
[ 10040-96-7 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 1151 - 1154

35
[ 76003-29-7 ]
[ 460-00-4 ]
[ 1284243-44-2 ]

Yield	Reaction Conditions	Operation in experiment
73%	With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine; In toluene;Inert atmosphere; Reflux;	A mixture of 1 ,1-dimethylethyl 3-oxo-1-piperazinecarboxylate (0.200 g, 0.999 mmol), 1-bromo-4-fluorobenzene (0.091 mL, 0.832 mmol), copper(l) iodide (0.008 g, 0.042 mmol), potassium carbonate (0.230 g, 1.665 mmol) and N,N'-dimethyl-1 ,2- ethanediamine (0.009 mL, 0.083 mmol) in toluene (5 mL) was heated at reflux under nitrogen overnight. The reaction mixture was filtered through silica gel. The filtrate was evaporated and the residue was purified by silica gel chromatography (EtOAc:hexane) to give1 ,1-dimethylethyl 4-(4-fluorophenyl)-3-oxo-1-piperazinecarboxylate (0.180 g, 73%) as a white solid.
27.2%	With copper(l) iodide; potassium hydrophosphate; N,N-dimethylethylenediamine; In toluene; at 25 - 80℃; for 16.0h;	To a solution of tert-butyl 3-oxopiperazine- 1 -carboxylate (prepared according to procedure reported in W02005504737, 2.0 g, 9.99 mmol), 1-bromo-4- fluorobenzene (1.748 g, 9.99 mmol), N,N-dimethylethylenediamine (0.070 g, 0.799 mmol) and potassium hydrophosphate (KHPO4) (3.13 g, 17.98 mmol) intoluene (10 ml) was added copper (I)iodide (0.101 g, 0.529 mmol) at 25C. The reaction mixture was heated to 80C for 16 h. Progress of the reaction was monitored by TLC. The reaction mixture was cooled to 25C, diluted with ethyl acetate (25 ml) and filtered through a plug of celite and concentrated to give crude product. The crude product was purified over silica gel (100 - 200 mesh)by column chromatography using 30% ethyl acetate in hexane as eluent to obtain the title compound (0.8 g, 27.2 %)?H NMR (400 MHz, CDC13) 6 7.28-7.24 (m, 2H), 7. 14-7.08 (m, 2H), 4.26 (s, 2H), 3.88-3.71 (m, 4H), 1.51(s, 9H). MS: m/z295(M+1).
27.2%	With dipotassium hydrogenphosphate; copper(l) iodide; N,N-dimethylethylenediamine; In toluene; at 25 - 80℃; for 16.0h;	Step 1: tert-butyl 4-(4-fluorophenyl)-3-oxopiperazine-1-carboxylate To a solution of tert-butyl 3-oxopiperazine-1-carboxylate (prepared according to procedure reported in WO2005504737, 2.0 g, 9.99 mmol), 1-bromo-4-fluorobenzene (1.748 g, 9.99 mmol), N,N-dimethylethylenediamine (0.070 g, 0.799 mmol) and potassium hydrophosphate (KHPO4) (3.13 g, 17.98 mmol) in toluene (10 ml) was added copper (I)iodide (0.101 g, 0.529 mmol) at 25 C. The reaction mixture was heated to 80 C. for 16 h. Progress of the reaction was monitored by TLC. The reaction mixture was cooled to 25 C., diluted with ethyl acetate (25 ml) and filtered through a plug of celite and concentrated to give crude product. The crude product was purified over silica gel (100-200 mesh) by column chromatography using 30% ethyl acetate in hexane as eluent to obtain the title compound (0.8 g, 27.2%) 1H NMR (400 MHz, CDCl3) delta 7.28-7.24 (m, 2H), 7.14-7.08 (m, 2H), 4.26 (s, 2H), 3.88-3.71 (m, 4H), 1.51 (s, 9H). MS: m/z 295 (M+1).

Reference： [1]Patent: WO2011/41713,2011,A2 .Location in patent: Page/Page column 152
[2]Patent: WO2014/9872,2014,A1 .Location in patent: Page/Page column 63; 64
[3]Patent: US2015/152118,2015,A1 .Location in patent: Paragraph 0382 - 0385

36
[ 460-00-4 ]
[ 224434-01-9 ]

Reference： [1]Tetrahedron Asymmetry,2011,vol. 22,p. 329 - 337
[2]Tetrahedron Asymmetry,2011,vol. 22,p. 329 - 337

37
[ 928664-98-6 ]
[ 460-00-4 ]
[ 459-22-3 ]

Reference： [1]Journal of the American Chemical Society,2011,vol. 133,p. 6948 - 6951

38
[ 53406-38-5 ]
[ 460-00-4 ]
[ 1309792-09-3 ]

Yield	Reaction Conditions	Operation in experiment
59%	With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; lithium chloride; sodium t-butanolate; In toluene; at 130℃; for 3h;Inert atmosphere;	A flame-dried resealable Schlenk tube was charged with Pd2(dba)3 (0.025 mmol, 2.5 mol %), Xantphos (0.05 mmol, 5 mol %), the solid reactant(s) (1.0 mmol of the <strong>[53406-38-5]1-aminoindole</strong>, 2.0 mmol of the aryl halide), LiCl (2.0 mmol) and NaOtBu (2.8 mmol). The Schlenk tube was capped with a rubber septum, evacuated, and backfilled with argon; this evacuation/backfill sequence was repeated one additional time. The liquid reactant(s) and toluene (2 mL per mmol) were added through the septum. The septum was replaced with a teflon screwcap. The Schlenk tube was sealed, and the mixture was stirred at 130 C for 3 h. The resulting suspension was cooled to room temperature and filtered through a pad of celite eluting with ethyl acetate, and the inorganic salts were removed. The filtrate was concentrated and purification of the residue by silica gel column chromatography gave the desired product. All the compounds gave satisfactory spectroscopic data. Data for the selected compounds are given below:Compound 4a: Yield: 60%; TLC : Rf 0.62 (c-hexane/AcOEt 8:2 IR (neat): 3311, 1608, 1581, 1455, 1368, 1252, 1131, 911, 821 cm-1; NMR (300 MHz) delta 7.52 (d, 1H, J = 7.6 Hz), 7.30 (d, 1H, J = 9.0 Hz), 7.15 (d, 1H, J = 3.4 Hz), 7.10-6.99 (m, 2H), 6.79 (d, 4H, J = 8.9 Hz), 6.66 (d, 4H, J = 8.9 Hz), 6.45 (d, 1H, J = 3.4 Hz), 3.62 (s, 3H), 3.61 (s, 3H). 13C NMR (75 MHz, CDCl3) delta 155.6 (2C), 139.8 (2C), 135.6, 127.6, 126.2, 122.7, 121.1, 120.5 (5C), 114.6 (4C), 109.9, 101.6, 55.5 (2C). m/z MS (ES+) 344.0 (M+).

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 2687 - 2691

39
[ 460-00-4 ]
[ 78782-17-9 ]
[ 243145-83-7 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 3368 - 3371

40
[ 141452-01-9 ]
[ 460-00-4 ]
[ 1252780-58-7 ]
[ 1252780-57-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 80℃;capped vial;	A mixture of compound 24a (500 mg, 2.82 mmol), 1-bromo-4-fluoro-benzene 24b (0.31 mL, 2.82 mmol), Pd2(dba)3 (129 mg, 0.14 mmol), BINAP (132 mg, 0.21 mmol), and sodium t-butoxide (325 mg, 3.39 mmol) in toluene (25 mL) was placed in a capped vial and heated at 80 C. overnight. The reaction mixture was then diluted with EtOAc and water, and the water layer was basified to pH8 with 1N aqueous NaOH. The organic layer was concentrated under reduced pressure and purified by flash column chromatography (silica gel, 5-30% EtOAc/heptane) to give a mixture of compound 24c (145 mg), MS m/z (M+H+) 272.1, and compound 24d (232 mg), MS m/z (M+H+) 258.0.

Reference： [1]Patent: US2012/101081,2012,A1 .Location in patent: Page/Page column 54; 55

41
[ 82104-74-3 ]
[ 460-00-4 ]
[ 260371-16-2 ]

Reference： [1]Organic Process Research and Development,2012,vol. 16,p. 824 - 829

42
[ 288-32-4 ]
[ 460-00-4 ]
[ 10040-96-7 ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 8012 - 8016

43
[ 460-00-4 ]
[ 530-46-1 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 4850 - 4853,4
[2]Chemistry - A European Journal,2016,vol. 22,p. 10420 - 10424

44
[ 460-00-4 ]
[ 163222-32-0 ]

Reference： [1]Patent: WO2012/155932,2012,A1
[2]Patent: CN105503686,2016,A

45
[ 460-00-4 ]
[ 1030825-20-7 ]

Reference： [1]Patent: WO2012/160218,2012,A1
[2]Patent: EP2918579,2015,A1

46
[ 6165-68-0 ]
[ 460-00-4 ]
[ 58861-48-6 ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium carbonate;tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine; In ethanol; water; at 90℃;Inert atmosphere;	Synthesis of compound 42C10H7FS M = 178.23 g.mol"1 19F NMR (CDCh 282.5MHz): -109.8 (m, IF, Ar-F).Mass (GC-MS): 133 (41%); 178 (100%)Into a freshly degassed mixture of EtOH (69mL) and H20 (9mL) was added Pd2dba3 (534mg, 0.58mmol, 0.025eq), PCy3 (660mg, 2.35mmol, O.leq), 2-thiophene boronic acid (3.00g, 23.4mmol, leq), K2C03 (6.48g, 46.9mmol, 2eq), and 4- bromofluorobenzene (5.17mL, 47.0mmol, 2eq). The resultant mixture was stirred overnight at 90C and then allowed to reach room temperature. MgS04 was added to quench water and the mixture was filtered on a pad of Celite using ethyl acetate. The filtrate was concentrated and purified on silica gel chromatography (cyclohexane/ ethyl acetate 100:0 to 95:5) to afford compound 42 (3.84g, 92% yield) as a white solid.

Reference： [1]Patent: WO2012/160218,2012,A1 .Location in patent: Page/Page column 71
[2]Chemistry - A European Journal,2015,vol. 21,p. 18407 - 18416
[3]Catalysis science and technology,2015,vol. 5,p. 2065 - 2071
[4]Angewandte Chemie - International Edition,2015,vol. 54,p. 5772 - 5776
Angew. Chem.,2015,vol. 127,p. 5864 - 5868,5
Angewandte Chemie,2015,vol. 127,p. 5864 - 5868,5

47
[ 374564-35-9 ]
[ 460-00-4 ]

Yield	Reaction Conditions	Operation in experiment
63%Spectr.	With lithium hydroxide monohydrate; silver trifluoromethanesulfonate; Selectfluor; In ethyl acetate; at 55℃;Sealed tube;	General procedure: Trifluoroborate (0.50 mmol, 1.0 equiv), LiOH·H2O (25.2 mg, 0.60 mmol, 1.2 equiv), Selectfluor (212 mg, 0.60 mmol, 1.2 equiv), AgOTf (386 mg, 1.5 mmol, 3.0 equiv) were weighed into a 20 mL microwave vial. EtOAc (5 mL) was added, and sealed with a microwave cap and the mixture was allowed to stir at 55 C for 5-15 h. The resulting solution was cooled to room temperature. For the compounds reported with isolated yields (2a, 2b, 2c, 2d, 2e, 2g, 2h, 2j, 2k, 2l, 2m, 2o, 2p, 2t, 2u, 2x, 2v, 2y, 2ab, 2ac, and 2ag) the reaction mixture was diluted with MTBE or hexane (5 mL) and H2O (4.0 mL). Then organic phase was separated, the aqueous phase was extracted with MTBE (2*5 mL). The combined organic phases were dried over anhydrous Na2SO4. The filtrate was concentrated in rotavapor and the residue was purified by column chromatography on Combiflash with hexanes/EtOAc to afford the desired compounds. The volatile and low yielding products were not isolated and their yields were determined only by 19F NMR of the reaction mixture. For the compounds reported with 19F NMR yields, 4-fluorobenzonitrile (0.50 mmol) was added as reference to the reaction mixture, stirred for 5 min, and then diluted with MTBE or hexane (5 mL) and H2O (3.0 mL). The layers were separated and an an aliquote of the organic phase was withdrawn for the 19F NMR measurement in CDCl3.

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 4648 - 4651
[2]Journal of the American Chemical Society,2013,vol. 135,p. 14012 - 14015
[3]Tetrahedron,2014,vol. 70,p. 9676 - 9681

48
[ 460-00-4 ]
[ 70441-63-3 ]

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 6225 - 6229

49
[ 5802-17-5 ]
[ 460-00-4 ]
[ 1370470-33-9 ]

Yield	Reaction Conditions	Operation in experiment
		A disolution of 4-fluor-1-bromobencen (1.5 eq) in anhydrous THF (8ml/nmol of bromo derivative), was added drop by drop under inert atmosphere over magnesium turnings (10 eq.). The mixture was activated by the addition of 1,2-dibromoethane and heated to reflux for 3 h. Once cooled to room temperature, a solution of the corresponding 6-metoxicroman-4-ona (1 eq.) was added dropwise in anhydrous THF (12 ml/mmol chromanone) and the mixture was heated to reflux for 3.5 h (). Once cooled at room temperature, saturated aqueous NH4Cl (12 ml/mmol chromanone) was added over 15 minutes. The product was extracted with t-butyl methyl ether (3 x 5 ml/mmol chromanone) and the combined organic phases were washed with saturated aqueous NaHCO3 until neutral, dried (MgSO4) and solvent was evaporated under reduced pressure. Then, the crude from the previous step was dissolved in dioxane (2 ml/mmol chromanone), an aqueous solution of H2SO4 20% v/v (12 ml/mmol chromanone) was added and heated at reflux for 3 h. The mixture was allowed to cool down to room temperature and neutralized. After evaporation of the dioxane, the product was extracted with t-butyl methyl ether (3 x 5 ml/mmol chromanone), washed with water, dried (MgSO4) and solvent evaporated under reduced pressure giving rise to the corresponding 4-(4-Fluorophenyl)-6-methoxy-2H-chromene as a white solid. If necessary, the product can be purified by column chromatography (silica, hexane / ethyl acetate 20:1).
		General procedure: The general method used to prepare the title compounds is shown below. Briefly, the corresponding chroman-4-one derivative was allowed to react with the appropriate phenylmagnesium salt followed by dehydration in acid medium to give the 4-substituted benzopyran adduct 2. Formylation of this intermediate using standard conditions yielded aldehyde 3, which was finally converted into the desired compound 4 by reductive amination. The commercial availability of the starting chroman-4-one that bears an additional phenyl group at C-2 facilitated the preparation of compound AX-024. Purification of final compounds was carried out by chromatography (preparative thin-layer or column) on silica gel.The synthetic sequence involved well-known reactions that give good overall yields of the final compounds, which were then purified by silica gel chromatography (preparative thin-layer or column). Rigorous structural characterization of the intermediates and compounds was carried out by analytical (HPLC) and spectroscopy (1H and 13C NMR, and HRMS). For preparation of the hydrochloride salt, a solution of AX-024 base in methanol (1 mmol/ml, total volume of 46 ml) was cooled to 0 C. in an ice-water mix and hydrochloric acid (4.6 mmol in 0.93 ml) was added dropwise. The mixture was allowed to react for 1 hour and the solvent was eliminated at low pressure.

Reference： [1]Patent: EP2623503,2013,A1 .Location in patent: Paragraph 0145; 0146; 0147
[2]Patent: US2019/231745,2019,A1 .Location in patent: Paragraph 0074; 0075

50
[ 1293389-28-2 ]
[ 460-00-4 ]
5,6-difluoro-4,7-bis(4-fluorophenyl)benzo[c][1,2,5]thiadiazole [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 16376 - 16379
[2]Journal of Organic Chemistry,2016,vol. 81,p. 360 - 370

51
[ 1864-94-4 ]
[ 460-00-4 ]
[ 2714-90-1 ]

Reference： [1]Chinese Journal of Chemistry,2013,vol. 31,p. 1488 - 1494

52
[ 460-00-4 ]
[ 780753-89-1 ]

Reference： [1]Patent: WO2014/9872,2014,A1

53
[ 1227382-01-5 ]
[ 460-00-4 ]
[ 1333215-19-2 ]

Reference： [1]Patent: US2014/221340,2014,A1

54
[ 1227382-01-5 ]
[ 460-00-4 ]
[ 1333215-20-5 ]

Yield	Reaction Conditions	Operation in experiment
48%	With tris-(dibenzylideneacetone)dipalladium(0); potassium tert-butylate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triethylamine; In toluene; at 110℃; for 24h;	6-(tert-Butoxycarbonyl)-6-aza-2-azospiro[3,3]heptane oxalate (Organic Letters, vol. 10, page 3525, 2008; 0.050 g, 0.103 mmol) was dissolved in toluene (2.5 mL), 1-bromo-4-fluorobenzene (0.036 g, 0.206 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.009 g, 0.010 mmol), (+-)-BINAP (0.019 g, 0.031 mmol), potassium tert-butoxide (0.069 g, 0.617 mmol) and triethylamine (0.005 g, 0.051 mmol) were added, and the mixture was stirred at 110 C. for 24 hr. The reaction mixture was allowed to cool to room temperature and filtered through Celite. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1) to give the title compound (0.029 g, 48%).

Reference： [1]Patent: US2014/221340,2014,A1 .Location in patent: Paragraph 0526

55
[ 90560-10-4 ]
[ 460-00-4 ]
[ 166975-72-0 ]

Yield	Reaction Conditions	Operation in experiment
54%	With chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2?,4?,6?-tri-1-propyl-1,1?-biphenyl][2-(2-aminoethyl)phenyl]palladium(II); potassium carbonate; Trimethylacetic acid; In N,N-dimethyl acetamide; at 150℃; for 2h;Microwave irradiation; Sealed tube; Inert atmosphere;	2-(4-fluorophenyl)-<strong>[90560-10-4]6-methoxybenzo[b]thiophene</strong> (compound 1) To a 5 mL microwave vial was added a solution of <strong>[90560-10-4]6-methoxybenzo[b]thiophene</strong> (400 mg, 2.44 mmol) in anhydrous DMA (3 mL) followed by 1-bromo-4-fluorobenzene (448 mg, 2.56 mmol), chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2',4',6'-tri-1-propyl-1,1'-biphenyl][2-(2-aminoethyl)phenyl]palladium(II) (BrettPhos palladacycle 1st generation, 97 mg, 0.12 mmol), trimethylacetic acid (746 mg, 7.31 mmol) and potassium carbonate (1.01 g, 7.31 mmol). The microwave vial was sealed, purged with nitrogen and subjected to microwave irradiation at 150° C. for 2 h. Upon completion the reaction mixture was diluted with water and extracted with EtOAc. The combined organic layers were then washed with brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The resulting crude material was purified via trituration 2* with heptane and the remaining triturate (containing some product) was concentrated and purified by column chromatography (SiO2, 0-30percent EtOAc/Heptane) to afford 2-(4-fluorophenyl)-<strong>[90560-10-4]6-methoxybenzo[b]thiophene</strong> (340 mg, 1.32 mmol, 54percent yield). 1H NMR (400 MHz, (CD3)2SO) delta ppm=3.79-3.93 (m, 3H), 7.01 (dd, J=8.59, 2.53 Hz, 1H), 7.24-7.42 (m, 2H), 7.56 (d, J=2.53 Hz, 1H), 7.67-7.86 (m, 4H). LC/MS (m/z, MH+): 258.8.

Reference： [1]Patent: US2014/235660,2014,A1 .Location in patent: Paragraph 0255; 0256; 0257
[2]Journal of Medicinal Chemistry,2018,vol. 61,p. 2837 - 2864

56
[ 3994-50-1 ]
[ 460-00-4 ]
5-(4-fluorophenyl)-1-methyl-4-nitro-1H-pyrazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With palladium diacetate; potassium carbonate; tricyclohexylphosphine tetrafluoroborate; In toluene; at 120℃; for 18h;Inert atmosphere;	General procedure: To a 8 mL glass vial equipped with a magnetic stirbar were sequentially added K2CO3 (207 mg, 1.5 mmol), the nitroazole substrate (0.50 mmol), aryl halide (0.50 mmol oras indicated), toluene (0.50 M or 1.0 M), Pd(OAc)2 (5.60mg, 0.025 mmol) and [PCy3H]BF4 (18.4 mg, 0.050 mmol).The reaction mixture was purged with nitrogen through aTeflon-lined cap. Then the cap was replaced with a newTeflon-lined solid cap. The reaction vial was moved to a preheatedreaction block. After stirring for 18 h at the indicatedtemperature, the reaction mixture was cooled to 25 C and concentrated. The residue was purified by flash column chromatography to provide the desired arylated product.

Reference： [1]Bulletin of the Korean Chemical Society,2014,vol. 35,p. 3009 - 3014

57
[ 460-00-4 ]
[ 697305-48-9 ]

Reference： [1]Patent: US2015/152118,2015,A1

58
[ 274-71-5 ]
[ 460-00-4 ]
3-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidine [ No CAS ]
C₁₈H₁₁F₂N₃ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 8787 - 8790
Angew. Chem.,2015,vol. 54,p. 8911 - 8914,4

59
[ 274-71-5 ]
[ 460-00-4 ]
7-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidine [ No CAS ]
C₁₈H₁₁F₂N₃ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 8787 - 8790
Angew. Chem.,2015,vol. 54,p. 8911 - 8914,4

60
[ 4488-22-6 ]
[ 460-00-4 ]
C₂₆H₁₉FN₂ [ No CAS ]

Reference： [1]Catalysis science and technology,2015,vol. 5,p. 4644 - 4652

61
[ 766-55-2 ]
[ 460-00-4 ]
3-(4-fluorophenyl)imidazo[1,2-b]pyridazine [ No CAS ]

Reference： [1]Chemistry - An Asian Journal,2016,vol. 11,p. 2443 - 2452

62
[ 5142-75-6 ]
[ 460-00-4 ]
[ 613-33-2 ]
[ 72093-43-7 ]

Yield	Reaction Conditions	Operation in experiment
	With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; triphenylphosphine; cesium fluoride; In N,N-dimethyl-formamide; at 90℃; for 1h;Inert atmosphere; Green chemistry;	General procedure: Under inert atmosphere (N2), in a 25 mL round bottom flask, Ar3Bi (0.208 mmol; 0.35 eq.), CsF (0.24 g: 1.8 mmol; 3 eq.), PPh3 (0.004 g: 0.018 mmol; 3 mol%), the aryl bromide (0.60 mmol; 1 eq.) was added to DMF (5 mL). The solution was warmed to 90 C prior addition of PEPPSI IPr (0.012 g: 0.018 mmol; 3 mol%). The reaction was monitored by GC/MS to follow the total consumption of the aryl bromide. Cooled to room temperature (RT), the reaction mixture was diluted by addition of diethyl ether (20 mL) and aqueous HCl 6 M (30 mL). After decantation, the aqueous solution was extracted with diethylether (2 * 20 mL). The collected organic phases were then washed with HCl 6 N (2 * 25 mL), water (25 mL) and brine (25 mL) prior drying over MgSO4. After concentration under reduced pressure, the resulting crude product was subjected to purification by column chromatography leading after concentration under reduced pressure to the title compound.

Reference： [1]Journal of Molecular Catalysis A: Chemical,2016,vol. 425,p. 94 - 102

63
[ 109384-19-2 ]
[ 460-00-4 ]
[ 889865-34-3 ]

Reference： [1]Patent: WO2015/88045,2015,A1
[2]Patent: WO2017/38909,2017,A1

64
[ 188290-36-0 ]
[ 460-00-4 ]
[ 58861-48-6 ]

Reference： [1]European Journal of Organic Chemistry,2017,vol. 2017,p. 111 - 123

65
[ 460-00-4 ]
[ 873566-75-7 ]

Reference： [1]Patent: CN103626791,2016,B

66
[ 2164-61-6 ]
[ 460-00-4 ]
3-(4-fluorophenyl)pyridazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With copper(I) oxide; tetrakis(triphenylphosphine) palladium(0); lithium carbonate; In N,N-dimethyl acetamide; at 160℃; for 24h;Molecular sieve; Inert atmosphere;	General procedure: To an 10 mL vial reaction vessel equipped with a magnetic stirring bar was added <strong>[2164-61-6]pyridazine-3-carboxylic acid</strong> (0.6 mmol, 1.0 eq), aryl- and heteroaryl-bromides (1.2 mmol, 2.0 eq), Pd(PPh3)4 (35 mg, 0.03 mmol, 5.0 mol %), Cu2O (84 mg, 0.6 mmol, 1.0 eq), Li2CO3 (107 mg, 1.8 mmol, 3.0 eq), 3A MS (200 mg) and DMA (4.0 mL). The mixture was stirred at 160 C for 24 h under N2. After the reaction was complete, the mixture was washed with brine and extracted with ethyl acetate three times. The combined organic layer was dried with anhydrous MgSO4 and evaporated in vacuum. The residue was purified by silica gel flash chromatography to produce the desired products (ethyl acetate / petroleum ether = 1/5 - 1/1), the eluent need bubbled NH3 five seconds. The eluent of TLC (ethyl acetate / petroleum ether 1:1) need bubbled NH3 two seconds.

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 1107 - 1111

67
[ 57266-69-0 ]
[ 460-00-4 ]
3-chloro-2-(4-fluorophenyl)pyridine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 3917 - 3925

68
[ 16478-52-7 ]
[ 460-00-4 ]
[ 1214324-71-6 ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 3917 - 3925

69
[ 20485-41-0 ]
[ 460-00-4 ]
[ 623577-48-0 ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 3917 - 3925

70
[ 460-00-4 ]
[ 152126-31-3 ]
3-fluoro-2-(4-fluorophenyl)pyridine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 3917 - 3925

71
[ 460-00-4 ]
[ 57631-11-5 ]

Reference： [1]Patent: WO2016/206101,2016,A1

72
[ 121219-12-3 ]
[ 460-00-4 ]
4-fluoro-4'-pentyl-1,1'-biphenyl [ No CAS ]

Reference： [1]Chemistry of Materials,2017,vol. 29,p. 3563 - 3571

73
[ 30384-96-4 ]
[ 460-00-4 ]
(6-bromoimidazo[1,2-a]pyridin-3-yl)-(4-fluorophenyl)methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%		To a suspension of magnesium (148 mg, 6.18 mmol) in THF (1 mL) was added 1-bromo-4-fluorobenzene (0.25 mL, 2.27 mmol) and the mixture was heated to 50C for a few seconds. The mixture was then stirred for 5 min and then the rest of 1-bromo-4-fluorobenzene (0.25 mL, 2.27 mmol) was added. The stirring was continued for 15 min and then the mixture was heated to 50C for about 30 min until most of the solid magnesium disappeared. The mixture was then allowed to cool to rt and 1 mL of this mixture was then treated with a solution of 6- bromoimidazo[1,2-a]pyridine-3-carbaldehyde (160 mg, 0.71 1 mmol) in THF (5 mL) at -30C and the mixture was stirred for 30 min. The reaction was then quenched by addition of a saturated solution of NH4Cl (5 mL) and then diluted in EtOAc (30 mL). The layers were separated and the aqueous layer was extracted with EtOAc (2 x 20 mL). The combined organic layers were washed with brine, dried and concentrated under reduced pressure. The material was purified by flash chromatography on silica gel using a mixture of EtOAc in hexane as eluent to provide the title compound (61%). MS (ESI) [M+H]+ 321.1/323.1;

Reference： [1]Patent: WO2017/66876,2017,A1 .Location in patent: Page/Page column 69

74
[ 106-38-7 ]
[ 460-00-4 ]
[ 247940-06-3 ]
dicyclohexyl(2'-(4-fluorophenyl)-6'-p-tolyl)-2-ylphosphine [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 7233 - 7237
Angew. Chem.,2017,vol. 129,p. 7339 - 7343,5

75
[ 460-00-4 ]
[ 247940-06-3 ]
2-dicyclohexylphosphino-2',6'-bis(4-fluorophenyl)biphenyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With chloro(1,5-cyclooctadiene)rhodium(I) dimer; lithium tert-butoxide; In 1,4-dioxane; at 140℃; for 36h;Schlenk technique; Inert atmosphere;	In a 25 mL Schlenk tube,A solution of 70.1 mg (0.2 mmol) of 2-dicyclohexylphosphino biphenyl (<strong>[247940-06-3]CyJohnPhos</strong>)(1,5-cyclooctadiene) chlorineRhodium (I) dimer 2.5 mg (2.5% mol of raw material), lithium tert-butoxide48 mg (0.6 mmol) Argon three times, under the protection of argon by adding 1,4-dioxane 1mL,4-fluorobromobenzene (84.0 mg, 0.48 mmol).Stirring at 140 C for 36 hours,After cooling to room temperature, the solvent was distilled off under reduced pressure, separated by 200-300 mesh silica gel column, petroleum ether: ethyl acetate = 100: 1 and dried in vacuo to give 89.9 mg of product as a white solid in 92% yield.

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 7233 - 7237
Angew. Chem.,2017,vol. 129,p. 7339 - 7343,5
[2]Patent: CN106674279,2017,A .Location in patent: Paragraph 0110; 0111

76
[ 657408-07-6 ]
C₂₂H₅₂N₂PdSi₄ [ No CAS ]
[ 460-00-4 ]
C₃₂H₃₉BrFO₂PPd [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2018,vol. 140,p. 126 - 130

77
[ 657408-07-6 ]
[ 460-00-4 ]
C₃₂H₄₀FO₃PPd [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2018,vol. 140,p. 126 - 130

78
[ 406482-20-0 ]
[ 460-00-4 ]
[ 1392440-74-2 ]

Reference： [1]ACS Catalysis,2018,vol. 8,p. 2989 - 2994

79
[ 53199-31-8 ]
[ 75-09-2 ]
[ 460-00-4 ]
[ 97472-13-4 ]
C₃₃H₅₄BrFP₂Pd*2.0CH₂Cl₂ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2018,vol. 140,p. 7979 - 7993

80
[ 15679-13-7 ]
[ 460-00-4 ]
5-(4-fluorophenyl)-2-isopropyl-4-methylthiazole [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2018,vol. 360,p. 3306 - 3317

81
[ 108149-63-9 ]
[ 460-00-4 ]
[ 1593201-05-8 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of (R)-4-Hydroxymethyl-2,2-dimethyl-oxazolidine-3 -carboxylic acid tert-butylester (0.66 g, 2.86 mmol) and DMF was added NaH (14 mg, 2 equiv.). After 5 mm., 1-Bromo-4-fluorobenzene 99% (0.31 ml, 2.86 mmol) was added. The mixture was then warmed to 80 C. After 16 h, the flask was cooled and to it added water and extracted with EtAOc. The organic layers are washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. Flash column chromatography was carried out using Hexanes - EtOAc to isolate tert-butyl (R)-4-((4-bromophenoxy)methyl)-2,2-dimethyloxazolidine-3 -carboxylate. [M+ 11 = 387.3.

Reference： [1]Patent: WO2018/195321,2018,A1 .Location in patent: Page/Page column 516

82
[ 460-00-4 ]
[ 398-21-0 ]

Reference： [1]Chemical Communications,2018,vol. 54,p. 13802 - 13804

83
[ 236406-39-6 ]
[ 460-00-4 ]
C₁₉H₂₇FN₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; In toluene; at 20℃;	To a stirring solution of 8 (60 mg, 0.3 mmol) in anhydrous toluene (5 mL) was added 1-bromo-4-fluorobenzene (45 mL,0.4 mmol), BINAP (19 mg, 0.03 mmol), t-BuONa (58 mg, 0.6 mmol),and Pd(OAc)2 (7 mg, 0.03 mmol) at room temperature. The mixture was stirred overnight at room temperature and filtered. The filtrate was diluted by H2O (15 mL), and extracted by DCM (10mL x 3). The combined organic layer was washed by brine, dried over anhydrous MgSO4, filtered, and concentrated. The residue was purified oversilica gel column (EtOAc: n-hexane =5 : 1) to yield oils 10c (58 mg,58%).

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 179,p. 208 - 217

84
[ 5381-25-9 ]
[ 460-00-4 ]
2-(4-fluorophenyl)-benzo[b]thiophene-3-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2019,vol. 361,p. 3925 - 3929

85
[ 5381-25-9 ]
[ 460-00-4 ]
C₁₅H₉FO₂S [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2019,vol. 361,p. 3925 - 3929

86
[ 5802-17-5 ]
[ 460-00-4 ]
4-(4-fluorophenyl)-6-methoxychroman-4-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A reaction vessel was charged with 1-Bromo-4-fluorobenzene (153 mL) and THF (1.125 L) and cooled to -78 C. to -70 C. Bu-Li in hexane (1.6M; 1.0 L) was added drop-wise to the reaction at -78 C. to -70 C. through an addition funnel over a period of 15-20 min. <strong>[5802-17-5]6-methoxychroman-4-one</strong> (225 g, 1.26 mol) dissolved in THF (1.125 L) was added drop-wise to the reaction at -78 C. to -70 C. through an addition funnel over a period of 15-20 min and the reaction was stirred for 2 h at the same temperature. After completion of the reaction, 10% NH4Cl solution was added to the reaction at -78 C. to -70 C. and the reaction mixture was gradually warmed to RT. The reaction mixture was extracted with ethyl acetate (1.125 L) and the combined organics were dried over anhydrous Na2SO4. The solvent was distilled off distilled off to yield a gummy mass of 4-(4-fluoro phenyl)-6-methoxy chroman-4-ol. The crude alcohol was dissolved in 1,4-dioxane and 20% H2SO4 solution (1.125 L) was added. The mixture was heated to reflux and maintained for 1 h. After completion of the reaction, the reaction was cooled to RT and extracted with ethyl acetate (1.125 L). The organic phase was dried over anhydrous Na2SO4 and the solvent distilled off completely to yield brown colored gummy mass of crude 4-(4-fluorophenyl)-6-methoxy-2H-chromene. Methanol (500 mL) was added to the crude mass of 4-(4-fluorophenyl)-6-methoxy-2H-chromene and cooled to 0 C. The precipitated solids were filtered to get pure 4-(4-fluorophenyl)-6-methoxy-2H-chromene (160 g, 49%).

Reference： [1]Patent: US2019/263792,2019,A1 .Location in patent: Paragraph 0468; 0471

87
[ 460-00-4 ]
[ 462-06-6 ]
[ 383-29-9 ]
[ 368-85-4 ]

Reference： [1]Chemical Communications,2019,vol. 55,p. 14753 - 14756

88
[ 824-79-3 ]
[ 460-00-4 ]
[ 613-33-2 ]
[ 72093-43-7 ]

Reference： [1]Journal of the American Chemical Society,2020

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Precautionary Statements-General
Code	Phrase
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P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
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Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
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P321
P322
P330	Rinse mouth.
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P332	IF SKIN irritation occurs:
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P335	Brush off loose particles from skin.
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P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
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P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
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P370	In case of fire:
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P378
P380	Evacuate area.
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P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
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Physical hazards
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H319	Causes serious eye irritation
H320	Causes eye irritation
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H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 460-00-4 ] {[proInfo.proName]}

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[ 460-00-4 ] Synthesis Path-Downstream 1~88

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