[ CAS No. 154549-38-9 ] {[proInfo.proName]}

Name: 154549-38-9|(2,4,6-Triisopropylphenyl)boronic acid|98%
Brand: Ambeed
SKU: A232829
Price: 5.0 USD
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Quality Control of [ 154549-38-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 154549-38-9 ]

Product Details of [ 154549-38-9 ]

CAS No. :	154549-38-9	MDL No. :	MFCD02683099
Formula :	C₁₅H₂₅BO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FGFYEKLWZBTLEW-UHFFFAOYSA-N
M.W :	248.17	Pubchem ID :	15153544
Synonyms :

Calculated chemistry of [ 154549-38-9 ]

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.6
Num. rotatable bonds :	4
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	80.01
TPSA :	40.46 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.83 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	4.2
Log Po/w (WLOGP) :	2.74
Log Po/w (MLOGP) :	2.93
Log Po/w (SILICOS-IT) :	2.41
Consensus Log Po/w :	2.46

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.01
Solubility :	0.0244 mg/ml ; 0.0000983 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.76
Solubility :	0.00432 mg/ml ; 0.0000174 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-3.76
Solubility :	0.0428 mg/ml ; 0.000173 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	2.31

Safety of [ 154549-38-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 154549-38-9 ]

* 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 [ 154549-38-9 ]
Downstream synthetic route of [ 154549-38-9 ]

[ 154549-38-9 ] Synthesis Path-Upstream 1~1

1
[ 21524-34-5 ]
[ 154549-38-9 ]

Reference： [1] Tetrahedron, 2000, vol. 56, # 49, p. 9655 - 9662

[ 154549-38-9 ] Synthesis Path-Downstream 1~88

1
[ 154549-38-9 ]
methyl 6-methoxy-2',4',6'-triisopropylbiphenyl-3-carboxylate [ No CAS ]

Reference： [1]Tetrahedron,2000,vol. 56,p. 9655 - 9662

2
[ 626-55-1 ]
[ 154549-38-9 ]
[ 1246888-92-5 ]

Reference： [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 5879 - 5883

3
[ 95-46-5 ]
[ 154549-38-9 ]
2,4,6-triisopropyl-2'-methylbiphenyl [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 5879 - 5883

4
[ 90-11-9 ]
[ 154549-38-9 ]
1-(2,4,6-triisopropylphenyl)naphthalene [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 5879 - 5883

5
[ 93777-26-5 ]
[ 154549-38-9 ]
[ 1269284-31-2 ]

Reference： [1]Organometallics,2011,vol. 30,p. 1607 - 1615

6
[ 154549-38-9 ]
[ 1269284-32-3 ]

Reference： [1]Organometallics,2011,vol. 30,p. 1607 - 1615

7
[ 154549-38-9 ]
[ 1269284-33-4 ]

Reference： [1]Organometallics,2011,vol. 30,p. 1607 - 1615

8
[ 1391976-73-0 ]
[ 154549-38-9 ]
[ 1391976-76-3 ]

Reference： [1]Chemical Communications,2012,vol. 48,p. 7808 - 7810
[2]Chemical Communications,2012,vol. 48,p. 7808 - 7810

9
[ 120-80-9 ]
[ 154549-38-9 ]
[ 1391976-79-6 ]

Reference： [1]Chemical Communications,2012,vol. 48,p. 7808 - 7810

10
[ 591-87-7 ]
[ 154549-38-9 ]
[ 1394213-93-4 ]

Reference： [1]Chemical Communications,2012,vol. 48,p. 8709 - 8711

11
[ 154549-38-9 ]
[ 1394213-82-1 ]

Reference： [1]Chemical Communications,2012,vol. 48,p. 8709 - 8711

12
(R)-6-bromo-N-(1-phenylethyl)thieno[2,3-d]pyrimidin-4-amine hydrochloride [ No CAS ]
[ 154549-38-9 ]
[ 1408055-36-6 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 110℃; for 22h;Inert atmosphere;	General procedure: Compound 11·HCl (201 mg, 0.543 mmol) was mixed with phenylboronic acid (5a) (104 mg, 0.850 mmol), finely powdered K2CO3 (301 mg, 2.18 mmol), Pd(PPh3)4 (32 mg, 0.028 mmol), 1,4-dioxane (2 mL) and water (2 mL). The reaction was then stirred at 110 C for 2 h under an N2 atmosphere. The solvent was removed and the product was dissolved in EtOAc (25 mL) and washed with water (3×20 mL) and saturated aq NaCl solution (15 mL). The organic phase was dried over Na2SO4, filtered, added HCl in diethyl ether (0.5 mL) and cooled to -18 C for 29 h. The resulting mixture was filtered and the solid material was washed with diethyl ether (3×15 mL).

Reference： [1]Tetrahedron,2012,vol. 68,p. 9226 - 9233

13
4-bromo-4’-(5-hexylthiophen-2-yl)-2,2’-bipyridine [ No CAS ]
[ 154549-38-9 ]
4-(5-hexylthiophene-2-yl)-4'-triisopropylphenyl-2,2'-bipyridine [ No CAS ]

Reference： [1]Journal of Materials Chemistry,2012,vol. 22,p. 18757 - 18760
[2]RSC Advances,2013,vol. 3,p. 26035 - 26046

14
4-bromo-4’-(5’-hexyl-2, 2’-bithiophen-5-yl)-2,2’-bipyridine [ No CAS ]
[ 154549-38-9 ]
4-(5'-hexyl-2,2'-bithiophen-5-yl)-4'-triisopropylphenyl-2,2'-bipyridine [ No CAS ]

Reference： [1]Journal of Materials Chemistry,2012,vol. 22,p. 18757 - 18760
[2]RSC Advances,2013,vol. 3,p. 26035 - 26046

15
[ 1416065-64-9 ]
[ 154549-38-9 ]
[ 1416065-69-4 ]

Yield	Reaction Conditions	Operation in experiment
14%	With sodium hydroxide;bis(tri-t-butylphosphine)palladium(0); In 1,4-dioxane; water; for 4h;Reflux;	A solution of 2-N-phenylamino-3-N-isopropylamino-6-chloropyridine ZW2 (2.00 g, 7.64 mmol, for preparation see ZW2, Example 4) in dioxane (100 ml) is admixed with sodium hydroxide solution (50% in H2O, 1.23 ml, 1.83 g, 22.9, 3.0 eq) and degassed, admixed with bis(tri-tert-butylphosphino)palladium (140 mg, 0.27 mmol, 3.5 mol %) and 2,4,6-triisopropylboronic acid (1.73 g, 6.98 mmol, 0.9 eq) and refluxed for 4 h. A further 40 ml of dioxane are added and the mixture is refluxed over the course of 92 h. The solvent is removed, and the mixture is taken up with dichloromethane and washed with water. The organic phase is removed and concentrated to dryness. The residue is purified by column chromatography (silica gel, CH:EA=3:2, then 9:1). Yield: 420 mg (14%). 1H NMR (CD2Cl2, 500 MHz): delta=1.08, 1.09 (2d, 12H), 1.26, 1.28 (2d, 12H), 2.70 (2*sept., 2H), 2.91 (sept., 1H), 3.22 (br.s., 1H), 3.62 (sept., 1H), 6.35 (br. s, 1H), 6.75 (d, 1H), 6.88 (t, 1H), 7.03 (mc, 3H), 7.22 (mc, 2H), 7.27-7.29 (m, 2H).
14%	With sodium hydroxide;bis(tri-t-butylphosphine)palladium(0); In 1,4-dioxane; water; for 96h;Reflux;	2-Lambda/-Phenylamino-3-Lambda/-isopropylamino-6-(2 4,-6,-triisopropylphenyl)pyridine:A solution of 2-/V-phenylamino-3-/V-isopropylamino-6-chloropyridine ZW2 (2.00 g, 7.64 mmol, for preparation see ZW2, Example 4) in dioxane (100 ml) is admixed with sodium hydroxide solution (50% in H20, 1 .23 ml, 1 .83 g, 22.9, 3.0 eq) and degassed, admixed with bis(tri-tert-butylphosphino)palladium (140 mg, 0.27 mmol, 3.5 mol%) and 2,4,6-triisopropylboronic acid (1.73 g, 6.98 mmol, 0.9 eq) and refluxed for 4 h. A further 40 ml of dioxane are added and the mixture is refluxed over the course of 92 h. The solvent is removed, and the mixture is taken up with dichloromethane and washed with water. The organic phase is removed and concentrated to dryness. The residue is purified by column chromatography (silica gel, CH:EA = 3:2, then 9:1 ). Yield: 420 mg (14%).

Reference： [1]Patent: US2012/319050,2012,A1 .Location in patent: Page/Page column 54
[2]Patent: WO2012/172482,2012,A1 .Location in patent: Page/Page column 107

16
[ 576-83-0 ]
[ 154549-38-9 ]
2,4,6-triisopropyl-2',4',6'-trimethylbiphenyl [ No CAS ]

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 2261 - 2265

17
[ 1564-64-3 ]
[ 154549-38-9 ]
9-(2,4,6-triisopropylphenyl)anthracene [ No CAS ]

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 2261 - 2265

18
[ 2586-62-1 ]
[ 154549-38-9 ]
[ 1263064-84-1 ]

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 2261 - 2265

19
[ 4357-57-7 ]
[ 154549-38-9 ]
9-(2,4,6-triisopropylphenyl)acridine [ No CAS ]

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 2261 - 2265

20
[ 6267-34-1 ]
[ 154549-38-9 ]
2,4,6-triisopropyl-4'-methoxy-2',6'-dimethylbiphenyl [ No CAS ]

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 2261 - 2265

21
C₁₈H₁₅BrO [ No CAS ]
[ 154549-38-9 ]
1-(2,4,6-triisopropylphenyl)-2-(benzyloxy)methylnaphthalene [ No CAS ]

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 2261 - 2265

22
[ 716-53-0 ]
[ 154549-38-9 ]
9-(2,4,6-triisopropylphenyl)anthracene [ No CAS ]

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 2261 - 2265

23
[ 13101-92-3 ]
[ 154549-38-9 ]
1-(2,4,6-triisopropylphenyl)-2-methoxynaphthalene [ No CAS ]

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 2261 - 2265

24
[ 56990-02-4 ]
[ 154549-38-9 ]
[ 1268853-57-1 ]

Yield	Reaction Conditions	Operation in experiment
85%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; water; at 95℃; for 24h;Inert atmosphere; Schlenk technique;	A mixture of 3,5-dibromobenzaldehyde (5 mmol), 2,4,6-trimethylphenylboronic acid (12 mmol), Pd(PPh3)4 (0.5 mmol), Na2CO3 (20 mmol) in 50 ml DME and 10 ml H2O was stirred under N2 at 95 for 24 h. After the mixture was washed by water, extracted by ether and evaporated, the residue was purified by flash column chromatography (hexane/ethyl acetate) to afford 3,5-di(2,4,6-trimethylphenyl)benzaldehyde with 85% yield. 1H NMR (250 MHz, CDCl3): delta 10.00 (s, 1H), 7.58 (d, J=1.64 Hz, 2H), 7.16 (t, J=1.65 Hz, 1H), 6.89 (s, 4H), 2.26 (s, 6H), 1.96 (s, 12H). 13C NMR (62.5 MHz, CDCl3): delta 192.543, 142.407, 137.436, 137.201, 137.016, 136.853, 135.660, 129.089, 128.322, 21.110, 20.837.

Reference： [1]Patent: US2013/30170,2013,A1 .Location in patent: Paragraph 0099; 0100

25
[ 153759-58-1 ]
[ 154549-38-9 ]
[ 1428318-93-7 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 4988 - 4991

26
[ 153759-58-1 ]
[ 154549-38-9 ]
[ 1428318-88-0 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 4988 - 4991

27
[ 34160-40-2 ]
[ 154549-38-9 ]
[ 1433897-26-7 ]

Yield	Reaction Conditions	Operation in experiment
72%	With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine; In toluene; at 100℃; for 72h;Glovebox; Inert atmosphere;	In a glove box, 6-bromo-2-pyridinecarboxaldehyde (500mg, 2.69mmol), <strong>[154549-38-9]2,4,6-triisopropylphenylboronic acid</strong> (767mg, 3.09mmol), triphenylphosphine (106mg, 0.403mmol), potassium phosphate (K3PO4, 1.43g, excess base), and tris(dibenzylideneacetone)dipalladium(0) (49.2mg, 0.054mmol) were added to a 20mL vial. Dry toluene (15mL) was added to the vial and the reaction mixture was heated to 100C for 3 days to produce a brown mixture. The reaction mixture was then cooled to room temperature, filtered through a thin pad of Celite, and subsequently eluted with diethyl ether (3×10mL) to extract the remaining product in the Celite pad. The filtrate (brown solution) was dried in vacuo to afford a brown solid. The solid was then washed with pentane (2×10mL) and dried in vacuo to yield the desired product as an ivory solid (595mg, 72%). 1H NMR (CDCl3, 500MHz): delta=10.10 (d, J=0.8Hz, 1H), 7.97-7.90 (m, 2H), 7.52 (dd, J=7.4, 1.3Hz, 1H), 7.10 (s, 2H), 2.95 (m, 1H), 2.44 (m, 2H), 1.29 (d, J=7.0Hz, 6H), 1.13 (d, J=6.9Hz, 6H), 1.09 (d, J=6.9Hz, 6H). 13C NMR (CDCl3, 125MHz): delta 194.3 (CAldehyde), 161.2, 152.7, 149.6, 146.4, 136.9, 135.3, 129.6, 121.2, 119.5 (9×CAromatic), 34.6, 30.6 (2×CBenzyl), 24.3, 24.2, 24.1 (3×CAlkyl) ppm. HRMS (EI) m/z calcd for C21H27NO 309.2093, found 309.2091.

Reference： [1]Journal of Organometallic Chemistry,2016,vol. 820,p. 1 - 7
[2]Organometallics,2013,vol. 32,p. 2952 - 2962
[3]Chemical Communications,2019,vol. 55,p. 9291 - 9294

28
[ 154549-38-9 ]
[ 1433897-00-7 ]

Reference： [1]Organometallics,2013,vol. 32,p. 2952 - 2962

29
[ 154549-38-9 ]
[ 1433897-62-1 ]

Reference： [1]Organometallics,2013,vol. 32,p. 2952 - 2962

30
[ 154549-38-9 ]
C₅₂H₆₂N₄Ni₂S₄ [ No CAS ]

Reference： [1]Organometallics,2013,vol. 32,p. 2952 - 2962

31
[ 154549-38-9 ]
[ 10330-42-4 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 14012 - 14015

32
[ 1353724-76-1 ]
[ 154549-38-9 ]
C₆₄H₉₂N₂O₂S₂ [ No CAS ]

Reference： [1]RSC Advances,2014,vol. 4,p. 732 - 742

33
[ 106-95-6 ]
[ 154549-38-9 ]
[ 1622081-68-8 ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 6211 - 6215
Angew. Chem.,2014,vol. 126,p. 6325 - 6329,5

34
[ 3132-99-8 ]
[ 154549-38-9 ]
[ 1620080-46-7 ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 10409 - 10411

35
[ 154549-38-9 ]
[ 1620080-48-9 ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 10409 - 10411

36
[ 154549-38-9 ]
[ 1620080-50-3 ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 10409 - 10411

37
C₅₁H₃₀Br₃IrN₁₂ [ No CAS ]
[ 154549-38-9 ]
C₉₆H₉₉IrN₁₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); In water; toluene;Inert atmosphere; Reflux;	Bromo-complex product (HI-I) of synthesis example 6 (0.20 g, 0.16 mmol),2,6-dimethylphenylboronic acid (0.18 g, 0.72 mmol), and K3P04 (0.21 g, 0.96 mmol) aresuspended in 120 ml of toluene and 24 ml of water. Argon is bubbled through the solution for 30 minutes and then tris-(dibenzylidenacetone)-dipalladium(0) (7 mg, 0.01 mmol) and Sphos (12 mg, 0.03 mmol) are added. The solution is purged with argon for 15 minutes and then heated to reflux under inert atmosphere overnight. After cooling to room temperature, phases are separated, the organic phase collected and the solvent removed. The solid is then purified via column chromatography (silica, cyclohexane/ethyl acetate). The title product is isolated as yellow solid (yield: 0.25 g (97%)).1HNMR (400 MHz, CD2CI2): = 8.62 (d, 3H, J = 1.4 Hz), 8.24 (d, 3H, J = 2.9 Hz), 8.04(d, 3H, J = 2.9 Hz), 7.41-7.18 ( br m, 3H), 7.18-7.05 (m, 6H, J = 7.5), 7.01 (s, 6H), 6.86 (d,3H, J = 7.4 Hz), 6.79 (t, 3H, J = 7.6 Hz), 6.73 (d, 3H, J = 7.6 Hz), 6.65-6.20 (br m, 6H),3.05-2.75 (m, 9H), 1.31 (d, 6H, J = 6.9 Hz), 1.18-1.14 (m, 18 H), 1.10 (d, 9H, J = 6.9 Hz),0.97 (d, 9H, J = 6.9 Hz).

Reference： [1]Patent: WO2015/14835,2015,A1 .Location in patent: Page/Page column 170; 171

38
[ 1611489-35-0 ]
[ 154549-38-9 ]
2-(2,4,6-triisopropylphenyl)benzimidazolo[2,1-b][1,3]benzothiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%		2.00 g (4.66 mmol) 2-bromo-9-iodo-benzimidazolo[2,1-b][1 ,3]benzothiazole, 2.04 g (6.99 mmol) <strong>[154549-38-9](2,4,6-triisopropylphenyl)boronic acid</strong>, 3.96 g (18.6 mmol) potassium phosphate tribasic in 80 ml toluene, 15 ml dioxane and 15 ml water are degased with argon. 340 mg (0.84 mmol) 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (sPhos) and 213 mg (0.23 mmol) tris(dibenzylidenaceton)dipalladium(0) (Pd2(dba)3) are added. The reaction mixture is degased with argon and stirred at 110 C for 27 h under argon. 40 ml 1 % sodiumcyanide solution is added to the reaction mixture and the reaction mixture is refluxed for 1 h. Water is added and the water phase is extracted with dichloromethane. The organic phase is dried with magnesium sulfate and the solvent is destilled off. The product is filtered on silica gel with dochloromethan. The product is decocted with methanol (yield: 1.89 g (65 %)). 1H NMR (400 MHz, [D6]DMSO): delta 8.47-8.49 (m, 2 H), 8.09 (d, J = 8.1 Hz, 1 H), 7.77 (d, J= 8.2 Hz, 1 H), 7.18 (dd, J = 1.4 Hz, J= 8.1 Hz, 1 H), 7.12 (dd, J= 1.4 Hz, J= 8.26 Hz, 2H), 7.06 (s, 2H), 7.04 (s, 1 H), 2.85-2.91 (m, 2H), 2.47-2.55 (m, superimposed), 1.21 (d, J= 6.9 Hz, 12H), 1.00-1.04 (m, 24H). MS (APCI(pos), m/z): 629 (M+1). 2-(2,4,6-triisopropylphenyl)benzimidazolo[2,1-b][1 ,3]benzothiazole is perpared in aniogy to Example 6 starting from 2-bromo-9-iodo-benzimidazolo[2,1-b][1 ,3]benzothiazole and (2,4,6- triisopropylphenyl)boronic acid (yield: 1.58 g (54 %)). 1H NMR (400 MHz, CDCl3): delta 7.87- 7.91 (m, 2H), 7.79-7.82 (m, 2H), 7.43-7.47 (m, 1 H), 7.34-7.39 (m, 1 H), 7.25-7.28 (m, 1 H), 7.15 (s, 2H), 3.01 (sep, J= 7 Hz, 1 H), 2.66 (sep, J= 6.9 Hz, 2H), 1.37 (d, J=6.9, 6H), 1.19 (d, J= 7 Hz, 6H), 1.14 (d, J= 7 Hz, 6 H).

Reference： [1]Patent: WO2015/14791,2015,A1 .Location in patent: Page/Page column 121; 122; 123

39
2-bromo-9-iodobenzo[d]benzo[4,5]imidazo[2,1-b]thiazole [ No CAS ]
[ 154549-38-9 ]
C₄₃H₅₂N₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%		2.00 g (4.66 mmol) 2-bromo-9-iodo-benzimidazolo[2,1-b][1 ,3]benzothiazole, 2.04 g (6.99 mmol) <strong>[154549-38-9](2,4,6-triisopropylphenyl)boronic acid</strong>, 3.96 g (18.6 mmol) potassium phosphate tribasic in 80 ml toluene, 15 ml dioxane and 15 ml water are degased with argon. 340 mg (0.84 mmol) 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (sPhos) and 213 mg (0.23 mmol) tris(dibenzylidenaceton)dipalladium(0) (Pd2(dba)3) are added. The reaction mixture is degased with argon and stirred at 110 C for 27 h under argon. 40 ml 1 % sodiumcyanide solution is added to the reaction mixture and the reaction mixture is refluxed for 1 h. Water is added and the water phase is extracted with dichloromethane. The organic phase is dried with magnesium sulfate and the solvent is destilled off. The product is filtered on silica gel with dochloromethan. The product is decocted with methanol (yield: 1.89 g (65 %)). 1H NMR (400 MHz, [D6]DMSO): delta 8.47-8.49 (m, 2 H), 8.09 (d, J = 8.1 Hz, 1 H), 7.77 (d, J= 8.2 Hz, 1 H), 7.18 (dd, J = 1.4 Hz, J= 8.1 Hz, 1 H), 7.12 (dd, J= 1.4 Hz, J= 8.26 Hz, 2H), 7.06 (s, 2H), 7.04 (s, 1 H), 2.85-2.91 (m, 2H), 2.47-2.55 (m, superimposed), 1.21 (d, J= 6.9 Hz, 12H), 1.00-1.04 (m, 24H). MS (APCI(pos), m/z): 629 (M+1).

Reference： [1]Patent: WO2015/14791,2015,A1 .Location in patent: Page/Page column 121

40
octyl 6-iodothieno[3,4-b]thiophene-2-carboxylate [ No CAS ]
[ 154549-38-9 ]
octyl 6-(2,4,6-triisopropylphenyl)thieno[3,4-b]thiophene-2-carboxylate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 10357 - 10366

41
octyl 4-iodothieno[3,4-b]thiophene-2-carboxylate [ No CAS ]
[ 154549-38-9 ]
octyl 4-(2,4,6-triisopropylphenyl)thieno[3,4-b]thiophene-2-carboxylate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 10357 - 10366

42
ethyl 4,6-dibromothieno[3,4-b]thiophene-2-carboxylate [ No CAS ]
[ 154549-38-9 ]
ethyl 4,6-bis(2,4,6-triisopropylphenyl)thieno[3,4-b]thiophene-2-carboxylate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 10357 - 10366

43
[ 154549-38-9 ]
[ 717-74-8 ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 9807 - 9816

44
7-chloroimidazo[1,2-f]phenanthridine [ No CAS ]
[ 154549-38-9 ]
7-(2,4,6-triisopropylphenyl)imidazo[1,2-f]phenanthridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2.6 g	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); In toluene; for 72h;Reflux; Inert atmosphere;	Step 1: Ligand Synthesis To a 500 mL round flask was added 7-chloroimidazo[1,2-f]phenanthridine (5.1 g, 20 mmol, prepared from the general procedure A), <strong>[154549-38-9]2,4,6-triisopropylphenylboronic acid</strong> (9.9 g, 40 mmol), Pd2(dba)3 (0.92 g, 1.0 mmol), 2-dicyclohexylphosphino-2?,6?-dimethoxybiphenyl (S-Phos, 1.64 g, 4.0 mmol), potassium phosphate tribasic (12.7 g, 60 mmol), and 200 mL of toluene. The reaction was heated to reflux and stirred under a nitrogen atmosphere for 72 hours. After cooling, the mixture was purified by a silica gel column. Yield was 2.6 g.
2.6 g	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); potassium phosphate monohydrate; In toluene; for 72h;Reflux; Inert atmosphere;	Step 1: Ligand Synthesis 500 round flask for 7-chloro-imidazo[1,2-f]phenanthridine (5.1 g, 20 mmol, generated from general procedure A), <strong>[154549-38-9](2,4,6-triisopropylphenyl)boronic acid</strong> (9.9 g, 40 mmol), Pd2 (dba) 3 (0.92 g, 1.0 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (S-Phos, 1.64 g, 4.0 mmol), potassium phosphate 3 basic (12.7 g, 60 mmol) was added to the toluene and 200 . The reaction was heated to reflux, and was goban for 72 hours under a nitrogen atmosphere. After cooling, the mixture was purified by a silica gel column. The yield is 2.6 g.

Reference： [1]Patent: US9281483,2016,B2 .Location in patent: Page/Page column 89
[2]Patent: KR2016/30582,2016,A .Location in patent: Paragraph 0213; 0214; 0215; 0216; 0217

45
[ 154549-38-9 ]
(2,6-diisopropylphenyl)[6-(2,4,6-triisopropylphenyl)pyridin-2-ylmethylene]amine [ No CAS ]

Reference： [1]Journal of Organometallic Chemistry,2016,vol. 820,p. 1 - 7
[2]Chemical Communications,2019,vol. 55,p. 9291 - 9294

46
[ 154549-38-9 ]
(2,4,6-trimethylphenyl)[6-(2,4,6-triisopropylphenyl)pyridin-2-ylmethylene]amine [ No CAS ]