[ CAS No. 64113-85-5 ] {[proInfo.proName]}

Name: 64113-85-5|4-Methyl-[1,1'-biphenyl]-2-carbonitrile|98%
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SKU: A201568
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Quality Control of [ 64113-85-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 64113-85-5 ]

SDS Specification

Alternatived Products of [ 64113-85-5 ]

Product Details of [ 64113-85-5 ]

CAS No. :	64113-85-5	MDL No. :	MFCD06411093
Formula :	C₁₄H₁₁N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QMSDNBJQBPHACW-UHFFFAOYSA-N
M.W :	193.24	Pubchem ID :	22283016
Synonyms :

Calculated chemistry of [ 64113-85-5 ] Expand+

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.07
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	61.56
TPSA :	23.79 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.9 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.5
Log Po/w (XLOGP3) :	3.63
Log Po/w (WLOGP) :	3.53
Log Po/w (MLOGP) :	3.26
Log Po/w (SILICOS-IT) :	4.01
Consensus Log Po/w :	3.39

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.85
Solubility :	0.0272 mg/ml ; 0.000141 mol/l
Class :	Soluble
Log S (Ali) :	-3.82
Solubility :	0.0294 mg/ml ; 0.000152 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-5.39
Solubility :	0.000787 mg/ml ; 0.00000407 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.99

Safety of [ 64113-85-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280	UN#:	N/A
Hazard Statements:	H302+H312+H332	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 64113-85-5 ]

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

Upstream synthesis route of [ 64113-85-5 ]
Downstream synthetic route of [ 64113-85-5 ]

[ 64113-85-5 ] Synthesis Path-Upstream 1~12

1
[ 106-38-7 ]
[ 2042-37-7 ]
[ 64113-85-5 ]

Yield	Reaction Conditions	Operation in experiment
88%	With hydrogenchloride; tert.-butyl lithium In tetrahydrofuran; hexane; ethyl acetate; pentane	Step A: 2-cyano-4--methylbiphenyl To a solution of p-bromotoluene (30 g) in dry ether (150 ml) at -78°C, a solution of t-BuLi in pentane (1.7M) (210 ml) was added slowly over a period of 1 hour and 30 minutes, using a dropping funnel. The bath was then removed and the mixture was stirred at room temperature for an additional 2 hours. The contents of the flask were then added slowly (using a cannula) at room temperature to a premixed soluiton of ZnCl₂ in ether (1M) (180 ml) and dry THF (360 ml). The mixture was stirred for 2 hours at that temperature and the the slurry was added (using a cannula) to a solution of 2-bromobenzonitrile (21.3 g) and NiCl₂(Ph₃P)₂ (2.1 g) in dry THF (300 ml). The mixture, after stirring at room temperature overnight (18 h), was poured slowly with stirring into ice-cold 1N HCl (1500 ml). The organic layer was separated and the aqueous phase was extracted with ether (3 X 300ml). The combined organic layer was washed with water, brine and then dried over MgSO₄. Removal of the solvent gave the crude product as a semisolid mass (34 g). The material was purified on a silica-gel flash column using ethyl acetate/hexane (1:12) to give the desired nitrile as a low-melting solid (28 g, 88percent). NMR(CDCl₃): δ 2.42 (S,3H), 7.2-7.8 (m,8H); FAB-MS: m/e 194 (M+H).

Reference： [1] Patent: EP400835, 1990, A1,
[2] Patent: EP456510, 1991, A1,
[3] Patent: EP426021, 1991, A1,

2
[ 2042-37-7 ]
[ 5720-05-8 ]
[ 64113-85-5 ]

Yield	Reaction Conditions	Operation in experiment
94%	With potassium carbonate In 5,5-dimethyl-1,3-cyclohexadiene	Example 2 165 mmol of bromobenzonitrile, 247 mmol of 4-methylphenylboronic acid, 330 mmol of potassium carbonate are heated with 0.2 mol percent of trans-di-acetato-bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II) in 300 ml of xylene for 16 hours at 130° C. The reaction solution is distilled after aqueous workup. Yield: 94percent of 2-cyano-4-methylbiphenyl.

Reference： [1] Patent: US5559277, 1996, A,

3
[ 873-32-5 ]
[ 5720-05-8 ]
[ 64113-85-5 ]

Yield	Reaction Conditions	Operation in experiment
73%	With potassium carbonate In 5,5-dimethyl-1,3-cyclohexadiene	Example 7 157 mmol of 2-chlorobenzonitrile, 236 mmol of 4-methylphenylboronic acid, 314 mmol of potassium carbonate are heated with 0.2 mol percent of trans-di-acetato-bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II) in 300 ml of xylene for 16 hours at 130° C. The reaction solution is recrystallized after aqueous workup. Yield: 73percent of 2-cyano-4-methylbiphenyl.

Reference： [1] Patent: US5559277, 1996, A,

4
[ 2042-37-7 ]
[ 5720-05-8 ]
[ 64113-85-5 ]

Yield	Reaction Conditions	Operation in experiment
80%	With sodium carbonate In methanol; water; toluene	Example 2 2M Sodium carbonate solution (200 ml) was added to a stirred mixture of 4-methylphenylboronic acid (30 g), 2-bromobenzonitrile (36.4 g), palladium (II) chloride (0.4 g), methanol (200 ml) and toluene (200 ml) at 5°C. The temperature rose to approximately 20°C and a solid precipitated. The reaction mixture was then heated at reflux for 2 hours. The reaction mixture was allowed to cool and water (100 ml) was added, followed by diatomaceous earth (5 g). The mixture was stirred for 15 minutes, then filtered through diatomaceous earth. The organic phase of the filtrate was separated and washed with 2M sodium carbonate solution and then water. The organic phase was then filtered and the filtrate evaporated. The resultant solid was recrystallized from petroleum ether (b.p. 110-120°C) to give 4--methylbiphenyl-2-carbonitrile (in 80percent yield) identical to that obtained in Example 1.

Reference： [1] Patent: EP470795, 1992, A1,

5
[ 54147-94-3 ]
[ 64113-85-5 ]

Reference： [1] Patent: US5206235, 1993, A,

6
[ 591-50-4 ]
[ 620-22-4 ]
[ 64113-85-5 ]

Reference： [1] Organic Letters, 2011, vol. 13, # 6, p. 1286 - 1289

7
[ 827-63-4 ]
[ 24388-23-6 ]
[ 64113-85-5 ]

Reference： [1] Organic Letters, 2018, vol. 20, # 20, p. 6573 - 6577

8
[ 2042-37-7 ]
[ 31614-66-1 ]
[ 64113-85-5 ]

Reference： [1] Patent: EP470794, 1992, A1,

9
[ 14221-01-3 ]
[ 2042-37-7 ]
[ 5720-05-8 ]
[ 497-19-8 ]
[ 64113-85-5 ]

Reference： [1] Patent: EP470795, 1992, A1,

10
[ 620-22-4 ]
[ 64113-85-5 ]

Reference： [1] Organic Letters, 2018, vol. 20, # 20, p. 6573 - 6577

11
[ 98-80-6 ]
[ 64113-85-5 ]

Reference： [1] Organic Letters, 2018, vol. 20, # 20, p. 6573 - 6577

12
[ 39554-87-5 ]
[ 151-50-8 ]
[ 64113-85-5 ]

Reference： [1] Journal of Organic Chemistry, 1978, vol. 43, # 2, p. 220 - 224

[ 64113-85-5 ] Synthesis Path-Downstream 1~26

1
[ 39554-87-5 ]
[ 151-50-8 ]
[ 64113-85-5 ]

Reference： [1]Journal of Organic Chemistry,1978,vol. 43,p. 220 - 224

3
tetrafluoroboric acid [ No CAS ]
[ 54147-94-3 ]
[ 64113-85-5 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; NaCN; sodium nitrite;CuCN; In water; dimethyl sulfoxide;	Step C: 3-Cyano-4-phenyltoluene To a cold (0 C.) suspension of 3-amino-4-phenyltoluene (1.97 g) in 2.65 mL of water and 2.65 mL of 12N HCl was slowly added a solution of sodium nitrite (738 mg) in 2 mL of water. To this yellowish slurry, 10 mL of fluoroboric acid was added with stirring. The cold mixture was filtered and the solid (2.02 g) washed with cold fluoroboric acid, ethanol and ether. A solution of this diazonium salt (2.02 g) in 5 mL of DMSO was added dropwise with cooling to a mixture of CuCN and NaCN in DMSO (13.3 mL). The reaction mixture was then diluted with water (20 mL) and extracted repeatedly with benzene. The combined organic layers were washed with water (2*) and brine and then dried over anhydrous MgSO4. Concentration under vacuum gave a reddish oil which was chromatographed on silica gel to give 0.788 g of product.

Reference： [1]Patent: US5206235,1993,A

4
[ 2042-37-7 ]
[ 5720-05-8 ]
[ 64113-85-5 ]

Yield	Reaction Conditions	Operation in experiment
94%	With potassium carbonate; In 5,5-dimethyl-1,3-cyclohexadiene;	Example 2 165 mmol of bromobenzonitrile, 247 mmol of 4-methylphenylboronic acid, 330 mmol of potassium carbonate are heated with 0.2 mol % of trans-di-acetato-bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II) in 300 ml of xylene for 16 hours at 130 C. The reaction solution is distilled after aqueous workup. Yield: 94% of 2-cyano-4-methylbiphenyl.

Reference： [1]Patent: US5559277,1996,A

5
[ 873-32-5 ]
[ 5720-05-8 ]
[ 64113-85-5 ]

Yield	Reaction Conditions	Operation in experiment
73%	With potassium carbonate; In 5,5-dimethyl-1,3-cyclohexadiene;	Example 7 157 mmol of 2-chlorobenzonitrile, 236 mmol of 4-methylphenylboronic acid, 314 mmol of potassium carbonate are heated with 0.2 mol % of trans-di-acetato-bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II) in 300 ml of xylene for 16 hours at 130 C. The reaction solution is recrystallized after aqueous workup. Yield: 73% of 2-cyano-4-methylbiphenyl.

Reference： [1]Patent: US5559277,1996,A

Yield	Reaction Conditions	Operation in experiment
88%		2-Cyano-4--methylbiphenyl To a solution of p-bromotoluene (30 g) in dry ether (150 ml) at -78C, a solution of t-BuLi in pentane (1.7M) (210 ml) was added slowly over a period of 1.5 hours, using a dropping funnel. The bath was then removed and the mixture was stirred at room temperature for an additional 2 hours. The contents of the flask was then added slowly (using a cannula) at room temperature to a premixed solution of ZnCl2 in ether (1M) (180 ml) and dry THF (360 ml). The mixture was stirred for 2 hours at that temperature and then the slurry was added (using a cannula) to a solution of 2-bromobenzonitrile (21.3 g) and NiCl2(Ph3P)2 (2.1 g) in dry THF (300ml). The mixture, after stirring at room temperature overnight (18 hours), was poured slowly under stirring into ice-cold 1N HCl (1500 ml). The organic layer was separated, and the aqueous phase was extracted with ether (3 x 300 ml). The combined organic layer was washed with water, brine and then dried over MgSO4. Removal of the solvent gave the crude product as a semisolid mass (34 g). The material was purified on a silica-gel flash column using ethyl acetate-hexane (1:12) to give the desired nitrile as a low-melting solid (28 g, 88%). 1H -NMR (CDCl3): 2.42 (s, 3H), 7.2-7.8 (m, 8H); FAB-MS: m/e 194 (M++1).
	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 100℃; for 0.75h;Sealed tube;	General procedure: To a 350 mL high-pressure vial was added tert-butyl 2-bromobenzoate (5.142 g, 20.0 mmol), p-tolylboronic acid (4.08 g, 30.0 mmol), Pd(PPh3)4(3.47 g, 3.0 mmol), potassium carbonate (8.29 g, 60.0 mmol) and dioxane with water (4:1, 200 mL). The mixture was degassed for 5 min and sealed. The mixture was heated at 100C for 40 min wherein analytical HPLC analysis indicated the completion of the reaction. The mixture was filtered through Celite and MeOH was used to wash the Celite pad. The solvent was removed and the crude was purified by flash chromatography (AcOEt /Hexane 0->30%) to obtain the title compound.

7
[ 14221-01-3 ]
[ 2042-37-7 ]
[ 5720-05-8 ]
[ 497-19-8 ]
[ 64113-85-5 ]

Yield	Reaction Conditions	Operation in experiment
	With dihydrogen peroxide; In water; toluene;	Example 1 4-Methylphenylboronic acid (1.62 g; 0.012 mole) was added to a solution of 2-bromobenzonitrile (1.82 g; 0.01 mole), tetrakis(triphenylphosphine)palladium(O) (0.35 g; 3 mole%) and 2M aqueous sodium carbonate solution (10 ml) in toluene (20 ml) and the mixture heated at 80C for 6 hours. The mixture was allowed to cool and hydrogen peroxide (30 wt. % solution in water; 0.5 ml) was added. The mixture was stirred for 20 minutes and then extracted with ether and the extracts dried (MgSO4). The solvent was removed by evaporation and the resultant oil purified by chromatography on silica eluding with 15% ethyl acetate/hexane to give 4--methylbiphenyl-2-carbonitrile as a solid (1.65 g), m.p. 44-46C; NMR(d6-DMSO): 2.40 (s, 3H), 7.30(d, 2H), 7.35-7.55 (m, 4H), 7.60-7.65(m, 1H), 7.75(d, 1H).

Reference： [1]Patent: EP470795,1992,A1

8
[ 2042-37-7 ]
[ 5720-05-8 ]
palladium dichloride [ No CAS ]
[ 64113-85-5 ]

Yield	Reaction Conditions	Operation in experiment
80%	With sodium carbonate; In methanol; water; toluene;	Example 2 2M Sodium carbonate solution (200 ml) was added to a stirred mixture of 4-methylphenylboronic acid (30 g), 2-bromobenzonitrile (36.4 g), palladium (II) chloride (0.4 g), methanol (200 ml) and toluene (200 ml) at 5C. The temperature rose to approximately 20C and a solid precipitated. The reaction mixture was then heated at reflux for 2 hours. The reaction mixture was allowed to cool and water (100 ml) was added, followed by diatomaceous earth (5 g). The mixture was stirred for 15 minutes, then filtered through diatomaceous earth. The organic phase of the filtrate was separated and washed with 2M sodium carbonate solution and then water. The organic phase was then filtered and the filtrate evaporated. The resultant solid was recrystallized from petroleum ether (b.p. 110-120C) to give 4--methylbiphenyl-2-carbonitrile (in 80% yield) identical to that obtained in Example 1.

Reference： [1]Patent: EP470795,1992,A1

9
[ 106-38-7 ]
[ 2042-37-7 ]
[ 64113-85-5 ]

Yield	Reaction Conditions	Operation in experiment
88%	With hydrogenchloride; tert.-butyl lithium;NiCl2(Ph3P)2; zinc(II) chloride; In tetrahydrofuran; hexane; ethyl acetate; pentane;	Step A: 2-cyano-4--methylbiphenyl To a solution of p-bromotoluene (30 g) in dry ether (150 ml) at -78C, a solution of t-BuLi in pentane (1.7M) (210 ml) was added slowly over a period of 1 hour and 30 minutes, using a dropping funnel. The bath was then removed and the mixture was stirred at room temperature for an additional 2 hours. The contents of the flask were then added slowly (using a cannula) at room temperature to a premixed soluiton of ZnCl2 in ether (1M) (180 ml) and dry THF (360 ml). The mixture was stirred for 2 hours at that temperature and the the slurry was added (using a cannula) to a solution of 2-bromobenzonitrile (21.3 g) and NiCl2(Ph3P)2 (2.1 g) in dry THF (300 ml). The mixture, after stirring at room temperature overnight (18 h), was poured slowly with stirring into ice-cold 1N HCl (1500 ml). The organic layer was separated and the aqueous phase was extracted with ether (3 X 300ml). The combined organic layer was washed with water, brine and then dried over MgSO4. Removal of the solvent gave the crude product as a semisolid mass (34 g). The material was purified on a silica-gel flash column using ethyl acetate/hexane (1:12) to give the desired nitrile as a low-melting solid (28 g, 88%). NMR(CDCl3): delta 2.42 (S,3H), 7.2-7.8 (m,8H); FAB-MS: m/e 194 (M+H).
	With hydrogenchloride; tert.-butyl lithium;NiCl2(Ph3P)2; zinc(II) chloride; In tetrahydrofuran; hexane; ethyl acetate; pentane;	Step 1 : 2-cyano-4--methylbiphenyl To a solution of p-bromotoluene (30 g) in dry ether (150 ml) at -78C, a solution of t-BuLi in pentane (1.7 M) (210 ml) was added slowly over a period of 1 hour and 30 minutes, using a dropping funnel. The bath was then removed and the mixture was stirred at room temperature for an additional 2 hours. The content of the flask was then added slowly (using a cannula) at room temperature to a premixed solution of ZnCl2 in ether (1 M) (180 mL) and dry THF (360 mL). The mixture was stirred for 2 hours at that temperature and the slurry was added (using a cannula) to a solution of 2-bromobenzonitrile (21.3 g) and NiCl2(Ph3P)2 (2.1 g) in dry THF (300 ml). The mixture, after stirring at room temperature overnight (18 hours), was poured slowly with stirring into ice cold 0.5 N HCl (1500 ml). The organic layer was separated, and the aqueous phase was extracted with ether (3 X 300 ml). The combined organic layer was washed with water, brine and then dried over MgSO4. Removal of the solvent gave the crude product as a semisolid mass (34 g). The material was purified on a silica gel flash column using ethylacetate/hexane (1:12) to give the desired nitrile as a low melting solid (28 g, 88%). NMR (CDCl3) delta 2.42 (s, 3H), 7.2-7.8 (m, 8H); FAB-MS: m/e 194 (M+H).
	With n-butyllithium;Zinc chloride; tetrakis(triphenylphosphine)palladium (0); In tetrahydrofuran; hexane; ethyl acetate;	Preparation 6 A solution of 1.5M butyllithium in hexane (25 ml) in tetrahydrofuran (25 ml) was cooled at -78C by using dry ice-acetone bath under nitrogen atmosphere and a solution of 4-bromotoluene (6.40 g) in tetrahydrofuran (25 ml) was added dropwise to the solution. After being stirred at -78C for 1 hour, a solution of freshly fused zinc chloride (5.15 g) in tetrahydrofuran (25 ml) was added in a slow stream via cannula and the resulting mixture was allowed to warm to room temperature. The mixture was stirred at room temperature for 1 hour and the resulting solution was added to a solution of 2-bromobenzonitrile (4.55 g) and tetrakis(triphenylphosphine)palladium(0) (400 mg) in tetrahydrofuran (25 ml) at room temperature. The solution was stirred at room temperature overnight. The solution was diluted with ethyl acetate (300 ml) and washed successively with 1N-hydrochloric acid, water, and brine. The organic solution was dried over magnesium sulfate and the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography with a mixture of ethyl acetate and n-hexane (1:20) as eluent to give 2-cyano-4--methylbiphenyl (4.43 g) as white powders. mp: 44-47C NMR (CDCl3, delta): 2.42 (3H, s), 7.25-7.35 (2H, m), 7.35-7.5 (4H, m), 7.62 (1H, dt, J=1, 7.5Hz), 7.85 (1H, dd, J=1, 7.5Hz)

Reference： [1]Patent: EP400835,1990,A1
[2]Patent: EP456510,1991,A1
[3]Patent: EP426021,1991,A1

10
[ 2042-37-7 ]
[ 31614-66-1 ]
[ 64113-85-5 ]

Yield	Reaction Conditions	Operation in experiment
	tetrakis(triphenylphosphine)palladium (0); In tetrahydrofuran;	Example 2 4-Methylphenyltributyl tin (A) (89.8 g) was added to a stirred solution of 2-bromobenzonitrile (43 g) and tetrakis(triphenylphosphine)palladium(0) (0.8 g) in THF (600 ml) under argon. The mixture was heated under reflux for 36 hours, then cooled and filtered through diatomaceous earth. The filtrate was washed with water (3x200 ml), dried (MgSO4) and the solvent removed by evaporation. The residue was distilled at 122-124C at 0.1 torr to give 4--methylbiphenyl-2-carbonitrile as a solid (28.9 g), m.p. 44-46C; NMR(CDCl3): 2.40(s, 3H), 7.30(d, 2H), 7.35-7.55(m, 4H), 7.60-7.65(m, 1H), 7.75(d, 1H).

Reference： [1]Patent: EP470794,1992,A1

11
[ 64113-85-5 ]
[ 1034689-14-9 ]

Yield	Reaction Conditions	Operation in experiment
86%		2-cyanobiphenyl-4-carboxylic acid, 11 The compound 9 (1.1 g, 6.0 mmol) is dissolved in pyridine (10 mL) and water (2 mL). To this solid, KMnO4 (0.9 g, 6.0 mmol, 1 equiv.) is added, and the reaction is heated to reflux. Additional 0.25 equiv. of KMnO4 is <n="13"/>added every 30 min. for 1O h. The reaction is further refluxed for 50 h and filtered hot and the filtrate is evaporated under reduced pressure. The residue is dissolved in 20 mL water with heating. The solution is acidified to pH 2 with cone. HCl after cooling to room temperature. The white precipitate is collected by filtration and washed generously with cold water and the product is dried under vacuum overnight. Yield 1.1 g, 86 %; mp 195-200 0C; 1HNMR (400 MHz, CDCl3) delta 2; 13CNMR (101 MHz, CDCl3) delta 2; IR (Neat, cm'1); GC-MS (EI) m/z (M+); Anal. (Ci4Hi ^0.0.75H2O) C, H, N.

Reference： [1]Patent: WO2008/92072,2008,A2 .Location in patent: Page/Page column 11-12

12
[ 591-50-4 ]
[ 620-22-4 ]
[ 64113-85-5 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 1286 - 1289

13
[ 110-82-7 ]
[ 64113-85-5 ]
[ 1613289-91-0 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 3396 - 3399

14
[ 64113-85-5 ]
[ 67-63-0 ]
[ 1859-13-8 ]
[ 1613290-14-4 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 3396 - 3399

15
[ 64113-85-5 ]
[ 114772-54-2 ]

Yield	Reaction Conditions	Operation in experiment
	With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; at 100℃; for 2.0h;	General procedure: To a 500 mL round-bottom flask was added tert-butyl 4'-methylbiphenyl-2- carboxylate (7.04 g, 26.23 mmol), NBS (5.14 g, 28.85 mmol), AIBN (0.43 g, 2.62 mmol) and CCl4(200 mL). The reaction mixture was refluxed for 2 h at 100C. The completion of the reaction was monitored by analytical HPLC. The reaction mixture was allowed to cool to room temperature and filtered. The filtrate was concentrated to obtain the crude product which was purified by flash chromatography (AcOEt/Hexane 0->30%) to obtain the title compoundThe title compound was prepared following the same protocol as described in Step 3, Example 1, using 4'-methyl-[1,1'-biphenyl]-2-carbonitrile instead of the tert-butyl 4?- methylbiphenyl-2-carboxylate and benzoyl peroxide instead of AIBN.1H NMR (400 MHz, DMSO-d6): (ppm) 4.79 (s, 2H, CH2), 7.55-7.68 (m, 6H, H2, H4, H5, H6, H7and H8biphenyl), 7.77 (t, J= 7.2 Hz, 1H, H3biphenyl), 7.93 (d, J= 7.2 Hz, 1H, H5biphenyl)

Reference： [1]Patent: WO2015/161108,2015,A1 .Location in patent: Page/Page column 241; 266; 267

16
[ 827-63-4 ]
[ 24388-23-6 ]
[ 64113-85-5 ]

Reference： [1]Organic Letters,2018,vol. 20,p. 6573 - 6577

17
[ 620-22-4 ]
[ 64113-85-5 ]

Reference： [1]Organic Letters,2018,vol. 20,p. 6573 - 6577

18
[ 98-80-6 ]
[ 64113-85-5 ]

Reference： [1]Organic Letters,2018,vol. 20,p. 6573 - 6577

19
[ 64113-85-5 ]
N-(2-methyl-9-(1-methyl-1H-imidazol-2-yl)-9H-fluoren-9-yl)acetamide [ No CAS ]