[ CAS No. 17745-45-8 ] {[proInfo.proName]}

Name: 17745-45-8|Propylboronic acid|98%
Brand: Ambeed
SKU: A224397
Price: 6.0 USD
Availability: InStock
Rating: 95 (29 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

2D 3D

Structure of 17745-45-8 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 17745-45-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 17745-45-8 ]

SDS Specification

Alternatived Products of [ 17745-45-8 ]

Product Details of [ 17745-45-8 ]

CAS No. :	17745-45-8	MDL No. :	MFCD01074564
Formula :	C₃H₉BO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JAQOMSTTXPGKTN-UHFFFAOYSA-N
M.W :	87.91	Pubchem ID :	351065
Synonyms :

Calculated chemistry of [ 17745-45-8 ]

Physicochemical Properties

Num. heavy atoms :	6
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	25.67
TPSA :	40.46 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.54 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	0.42
Log Po/w (WLOGP) :	-0.13
Log Po/w (MLOGP) :	-0.63
Log Po/w (SILICOS-IT) :	-1.67
Consensus Log Po/w :	-0.4

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.52
Solubility :	26.7 mg/ml ; 0.304 mol/l
Class :	Very soluble
Log S (Ali) :	-0.84
Solubility :	12.8 mg/ml ; 0.146 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	0.13
Solubility :	120.0 mg/ml ; 1.36 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.43

Safety of [ 17745-45-8 ]

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 [ 17745-45-8 ]

* 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 [ 17745-45-8 ]
Downstream synthetic route of [ 17745-45-8 ]

[ 17745-45-8 ] Synthesis Path-Upstream 1~11

1
[ 17745-45-8 ]
[ 40483-97-4 ]
[ 54965-21-8 ]

Yield	Reaction Conditions	Operation in experiment
41%	at 100℃; for 20 h;	In the flask, add 1.18 g 5 - nitrobenzimidazole -2 - amino methyl formate, 0.8 g n-propyl boric acid, 0.4 g sulfur, 0.5 g sodium hydroxide, 0.1 g cuprous iodide and 10 g polyethylene glycol, stirring under heating to 100 °C, continuously stirred for 20 hours, after the reaction, the obtained product B, the mixed product to B is poured into 100 ml ice water, adding hydrochloric acid (31 wt percent) in and to the pH to 7 - 8, precipitate, precipitated after completely, filtered, the filter cake washed for three times, dried, to obtain 0.55 g methyl [5-(propylthio)-1H-benzimidazol-2-yl]carbamate is albendazole.

Reference： [1] Patent: CN108530367, 2018, A, . Location in patent: Paragraph 0036; 0039

2
[ 121-43-7 ]
[ 927-77-5 ]
[ 17745-45-8 ]

Reference： [1] Journal of the American Chemical Society, 1938, vol. 60, p. 105 - 111
[2] , Gmelin Handbook: B: SVol.1, 4.8.4, page 224 - 226,
[3] Journal of the American Chemical Society, 1938, vol. 60, p. 110
[4] Ber., 1909, vol. 42, p. 3090 - 3096
[5] , Gmelin Handbook: B: SVol.1, 4.8.4, page 224 - 226,

3
[ 1116-61-6 ]
[ 17745-45-8 ]

Reference： [1] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 14, p. 1451
[2] Chemische Berichte, 1921, vol. 54, p. 2789
[3] Ber., 1921, vol. 54, p. 2784 - 2791
[4] , Gmelin Handbook: B: SVol.1, 4.8.4, page 224 - 226,
[5] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 14, p. 1452

4
[ 19567-27-2 ]
[ 17745-45-8 ]
[ 11113-50-1 ]

Reference： [1] Journal of the American Chemical Society, 1936, vol. 58, p. 407
[2] , Gmelin Handbook: B: B-Verb.14, 5, page 201 - 212,

5
[ 68498-84-0 ]
[ 927-77-5 ]
[ 17745-45-8 ]

Reference： [1] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1961, vol. 253, p. 1812 - 1814

6
[ 94408-59-0 ]
[ 17745-45-8 ]

Reference： [1] Zeitschrift fuer Anorganische und Allgemeine Chemie, 1963, vol. 324, p. 129 - 145
[2] , Gmelin Handbook: B: B-Verb.4, 9.1, page 268 - 279,

7
[ 1739-52-2 ]
[ 17745-45-8 ]

Reference： [1] Journal of the Chemical Society, 1964, p. 740 - 745

8
[ 1739-52-2 ]
[ 17745-45-8 ]
[ 7325-08-8 ]

Reference： [1] Journal of the Chemical Society, 1964, p. 740 - 745
[2] , Gmelin Handbook: B: B-Verb.9, 4.3.1.2, page 135 - 136,

9
[ 108-20-3 ]
[ 17745-45-8 ]

Reference： [1] Collection of Czechoslovak Chemical Communications, 1968, vol. 33, p. 976 - 979

10
[ 1739-52-2 ]
[ 7732-18-5 ]
[ 17745-45-8 ]

Reference： [1] Journal of the Chemical Society, 1964, vol. 1964, p. 740 - 745
[2] , Gmelin Handbook: B: B-Verb.9, 5.2.3, page 182 - 189,

11
[ 41453-14-9 ]
[ 540-73-8 ]
[ 17745-45-8 ]
[ 13940-22-2 ]

Reference： [1] Chemische Berichte, 1973, vol. 106, p. 1012
[2] , Gmelin Handbook: B: B-Verb.3, 4.7, page 82 - 86,

[ 17745-45-8 ] Synthesis Path-Downstream 1~88

1
[ 1116-61-6 ]
[ 17745-45-8 ]

Reference： [1]Chemische Berichte,1921,vol. 54,p. 2789
[2]Chemische Berichte,1921,vol. 54,p. 2784 - 2791
[3]Patent: DE371467,
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 14,p. 1452

2
[ 121-43-7 ]
[ 927-77-5 ]
[ 17745-45-8 ]

Reference： [1]Journal of the American Chemical Society,1938,vol. 60,p. 105 - 111
[2]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: B: SVol.1, 4.8.4, page 224 - 226
[3]Journal of the American Chemical Society,1938,vol. 60,p. 110
[4]Chemische Berichte,1909,vol. 42,p. 3090 - 3096
[5]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: B: SVol.1, 4.8.4, page 224 - 226

3
[ 17745-45-8 ]
[ 7325-08-8 ]

Reference： [1]Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1958,p. 860,863;engl.Ausg.S.835,837
[2]Journal of the American Chemical Society,1957,vol. 79,p. 5179

4
[ 17745-45-8 ]
[ 2440-40-6 ]

Reference： [1]Journal of the Chemical Society,1934,p. 405,408

5
[ 108-20-3 ]
[ 17745-45-8 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1968,vol. 33,p. 976 - 979

6
[ 1739-52-2 ]
[ 17745-45-8 ]

Reference： [1]Journal of the Chemical Society,1964,p. 740 - 745

7
[ 68498-84-0 ]
[ 927-77-5 ]
[ 17745-45-8 ]

Reference： [1]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1961,vol. 253,p. 1812 - 1814

8
[ 17745-45-8 ]
[ 71-36-3 ]
[ 4211-63-6 ]

Reference： [1]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1961,vol. 253,p. 1812 - 1814

9
[ 114834-29-6 ]
[ 17745-45-8 ]
2-propyl-4-(2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-henicosafluorodecyl)-[1,3,2]dioxaborolane [ No CAS ]

Reference： [1]Journal of Fluorine Chemistry,2005,vol. 126,p. 996 - 1001

10
[ 17745-45-8 ]
[ 149806-06-4 ]
[ 143142-34-1 ]

Yield	Reaction Conditions	Operation in experiment
31%		Reagents: i) 1-Propaneboronic acid, 31%; ii) Ethyl acrylate ; iii) NaOH, total yield of the two steps was ~24%.LC/MS data of 2805C - Calculated MW is 205; observed (the peak at 13.4 min, TIC): 206[M+H]. Gradient: 0-5 min: 10% ACN; 5-20 min: 10-30% ACN.

Reference： [1]Patent: WO2008/16968,2008,A2 .Location in patent: Page/Page column 71

11
methyl{1-[5-chloro-2-(trifluoromethyl)benzyl]-2-[4-(trifluoromethyl)phenyl]piperidin-4-yl}acetate [ No CAS ]
[ 17745-45-8 ]
methyl{1-[2-(trifluoromethyl)benzyl]-2-[4-(trifluoromethyl)phenyl]piperidin-4-yl}acetate [ No CAS ]
methyl{1-[5-propyl-2-(trifluoromethyl)benzyl]-2-[4-(trifluoromethyl)phenyl]piperidin-4-yl}acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
24%; 48%	With oxygen; caesium carbonate; In tetrahydrofuran; at 130℃; for 2h;Microwave;	Dihydrogen di-/iota-chlorotetrakis(di-tert-butylphosphinito-kappaP)dipalladate(2-) (POPdI, 38mg, 0.04mmol) was added to a clear solution of methyl { l-[5-chloro-2-(trifluoromethyl)benzyl]-2-[4- (trifluoromethyl)phenyl]piperidin-4-yl}acetate (200mg, 0.41mmol), n<strong>[17745-45-8]propylboronic acid</strong> (54mg, 0.62mmol) and cesium carbonate (401mg, 1.23mmol) in THF (3ml) in air. The yellow solution was then stirred at 1300C in the microwave for 2 h. The dark yellow solution was diluted with H2O (20ml) and extracted with EtOAc (2x20ml). Extracts were washed with H2O (20ml), brine (10ml) and dried (MgSO^. Solvent was removed in vacuo to yield a yellow gum (221mg).The mixture was purified by chromatography eluting with 5% EtOAc/isohexane to yield the title compound as a clear gum, (98mg, 48%). 1H NMR (400 MHz, CDCl3) delta: 0.98 (3H, t, J 7.3), 1.42-1.24 (2H, m), 1.72-1.68 (3H, m), 1.89-1.85 (IH, m), 2.11-1.97 (2H, m), 2.31-2.21 (2H, m), 2.66 (2H, t, J 7.6), 2.93-2.89 (IH, m), 3.21 (IH, dd, J 1.9, 15.0), 3.36 (IH, dd, J 2.8, 11.2), 3.58 (IH, s), 3.65 (4H, s), 7.08 (IH, d, J 8.0), 7.45 (IH, d, J 8.0), 7.55 (4H, s), 7.68 (IH, s); M/Z (ES+) 502 (MH+).Also obtained from the chromatography was methyl { l-[2-(trifluoromethyl)benzyl]-2-[4- (trifluoromethyl)phenyl]piperidin-4-yl} acetate as a clear gum, (46mg, 24%). 1H NMR (400 MHz, CDCl3) delta: 1.42-1.32 (2H, m), 1.71 (IH, dd, J 2.8, 9.9), 1.89-1.85 (IH, m), 2.13-1.97 (2H, m), 2.31-2.19 (2H, m), 2.92-2.88 (IH, m), 3.25 (IH, dd, J 1.9, 15.1), 3.38 (IH, dd, J 2.9, 11.2), 3.62 (4H, t, J 9.8), 7.29 (IH, t, J 7.7), 7.54 (6H, t, J 6.2), 7.91 (IH, d, J 7.7); M/Z (ES+) 460 (MH+).

Reference： [1]Patent: WO2006/43064,2006,A1 .Location in patent: Page/Page column 63

12
[ 3510-66-5 ]
[ 17745-45-8 ]
[ 18113-79-6 ]

Yield	Reaction Conditions	Operation in experiment
24%		i) 5-Methyl-2-propyl-pyridine5-Methyl-2-propyl-pyridine was prepared by Suzuki coupling of 2-bromo-5-methylpyridine and <strong>[17745-45-8]propylboronic acid</strong> according to the procedure given in Tetrahedron Letters 2002, 43, 6987-6990. The desired product was obtained in 24% yield after purification on silica gel.

Reference： [1]Patent: WO2007/71358,2007,A1 .Location in patent: Page/Page column 46

13
[ 1739-52-2 ]
[ 7732-18-5 ]
[ 17745-45-8 ]

Reference： [1]Journal of the Chemical Society,1964,vol. 1964,p. 740 - 745

14
[ 17745-45-8 ]
[ 540-54-5 ]
[ 11113-50-1 ]

Reference： [1]Journal of the Chemical Society,
Journal of the Chemical Society,1934,p. 405 - 411
[2]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: B: SVol.1, 4.8.4, page 224 - 226

15
[ 1739-52-2 ]
[ 17745-45-8 ]
[ 7325-08-8 ]

Reference： [1]Journal of the Chemical Society,
Journal of the Chemical Society,1964,p. 740 - 745

16
[ 94408-59-0 ]
[ 17745-45-8 ]

Reference： [1]Zeitschrift fur Anorganische und Allgemeine Chemie,
Zeitschrift fuer Anorganische und Allgemeine Chemie,1963,vol. 324,p. 129 - 145
[2]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: B: B-Verb.4, 9.1, page 268 - 279

17
[ 41453-14-9 ]
[ 540-73-8 ]
[ 17745-45-8 ]
[ 13940-22-2 ]

Reference： [1]Chemische Berichte,1973,vol. 106,p. 1012

18
[ 19567-27-2 ]
[ 17745-45-8 ]
[ 11113-50-1 ]

Reference： [1]Journal of the American Chemical Society,1936,vol. 58,p. 407
[2]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: B: B-Verb.14, 5, page 201 - 212

19
[ 17745-45-8 ]
[ 944334-36-5 ]
[ 944334-37-6 ]

Yield	Reaction Conditions	Operation in experiment
38%	With potassium phosphate;palladium diacetate; catacxium A; In water; toluene; at 100℃; for 5.5h;	20-(b) 3-Propyl-1,5-bis(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one; To 2.37 g (5.00 mmol) of 3-bromo-1,5-bis(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one obtained in Reference example 20-(a) were added 1.76 g (20 mmol) of <strong>[17745-45-8]propylboronic acid</strong>, 4.25 g (20 mmol) of potassium phosphate, 15.8 ml of toluene, 0.95 ml of water, 56 mg of palladium acetate and 179 mg of butyl-di-1-adamantylphosphine, and the mixture was degassed under reduced pressure, replaced with argon and stirred at 100C for 5.5 hours. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with toluene. The organic layer after separation was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was applied to silica gel column chromatography (Eluent; hexane:ethyl acetate=7:1->5:1 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 834 mg of the title compound as a pale brownish solid. (Yield: 38%) Mass Spectrum (CI, m/z): 438 (M++1). 1H-NMR Spectrum (CDCl3, delta ppm): -0.04 (s, 9H), -0.02 (s, 9H), 0.85-0.93 (m, 2H), 0.93-1.03 (m, 2H), 0.96 (t, J=7.5 Hz, 3H), 1.65-1.78 (m, 2H), 2.86 (td, J=7.5, 0.6 Hz, 2H), 3.43-3.51 (m, 2H), 3.68-3.75 (m, 2H), 5.38 (s, 2H), 5.57 (s, 2H), 6.87 (t, J=0.6 Hz, 1H), 8.12 (s, 1H).

Reference： [1]Patent: EP1982986,2008,A1 .Location in patent: Page/Page column 225

20
[ 247592-51-4 ]
[ 17745-45-8 ]
[ 1049684-94-7 ]

Yield	Reaction Conditions	Operation in experiment
	In toluene; for 5h;	EXAMPLE 5. Preparation of (6-cyanomethyl-2-propyl-[l,3,2]dioxaborinane-4-yl)- acetic acid t-butyl ester(FIG. 12)<63> The 6-cyano-3,5-dihydroxy-hexanoic acid t-butyl ester obtained from EXAMPLE 3 was diluted with 100 ml of toluene, followed by the addition of 3 g of propyl boronic acid. The contents were then subjected to azeotropic distillation over a period of 5 hours to remove water. Upon completion, toluene was removed and the residue was treated with 100 ml of diethyl ether to afford the title compound(7 g).<64> 1HNMR (CDCl3, 300MHz):0.6(2H, t), 0.9(3H, t), 1.3(9H, s), 1.6(2H, t), <n="10"/>2.4(2H1 d), 2.6(2H, d) , 3.2(1H, m), 3.9(1H, m) .

Reference： [1]Patent: WO2008/103016,2008,A1 .Location in patent: Page/Page column 8-9

21
[ 17745-45-8 ]
[ 956904-10-2 ]
[ 957206-32-5 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene;Heating / reflux;	To a toluene solution (15 mL) of 4-trifluoromethanesulfonyloxy-3-trifluoromethylbenzoic acid methyl ester (1.06 g), <strong>[17745-45-8]propylboronic acid</strong> (527 mg), cesium carbonate (4.89 g), water (7.5 mL), and tetrakis(triphenylphosphine)palladium(0) (347 mg) were added, and the mixture was stirred overnight at reflux. The resultant mixture was left to stand to cool to room temperature. Saturated aqueous sodium bicarbonate solution was added thereto, followed by extraction thrice, each with diethyl ether. The extracts were combined and washed with saturated brine, followed by drying over sodium sulfate anhydrate. Insoluble matter was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography (Yamazen Hi-Flash column 2L), whereby the title compound (628 mg) was yielded. 1H-NMR (CDCl3) delta: 1.01(3H,t,J=7.4Hz),1.63-1.72(2H,m),2.79-2.83(2H,m),3.94(3H,s),7.42(1H,d,J=8.1Hz),8.11(1H,dd,J=1.6,8.1 Hz),8.29(1H,d,J=1.6Hz). MS(ESI)m/z: 247(M+H)+.

Reference： [1]Patent: EP2017263,2009,A1 .Location in patent: Page/Page column 210-211

22
[ 17745-45-8 ]
[ 1093232-01-9 ]
[ 1093232-03-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 9498 - 9510

23
[ 17745-45-8 ]
[ 1093232-02-0 ]
[ 1093232-06-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 9498 - 9510

24
[ 17745-45-8 ]
[ 1114974-30-9 ]
[ 1114974-38-7 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; silver(l) oxide;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; at 80℃;	Ethyl [4-(l,3-dioxo-4,9-bis[(trifluoromethyl)sulfonyl]oxy}-l,3-dihydro-2H- benzo[f]isoindol-2-yl)phenyl]acetate (D19) (150mg, 0.23mmol) was added to a mixture of <strong>[17745-45-8]n-propyl boronic acid</strong> (45mg, 0.51mmol), PdCl2(dppf) (18mg, 0.02mmol), silver (I) oxide (133mg, 0.57mmol) and potassium carbonate (95mg, 0.69mmol) suspended in THF (5ml). Mixture was heated at 8O0C overnight. A further 2.5eq of silver oxide and 3eq of potassium carbonate and 0. leq of PdCl2(dppf) was added and continued heating for a further 7 hours. Reaction cooled to room temperature and <n="40"/>portioned between ethyl acetate (10ml) and water (10ml). Aqueous was extracted with ethyl acetate (2x1 OmI). Combined organics dried over magnesium sulphate and evaporated to a yellow oil. Crude material was purified by flash chromatography, eluting 0-20% ethyl acetate in hexane. Fractions evaporated to give the title compound as a white solid (18mg, 0.04mmol).LC/MS: Rt=4.20, [MH]+ 444.

Reference： [1]Patent: WO2009/19281,2009,A1 .Location in patent: Page/Page column 38-39

25
[ 851776-64-2 ]
[ 17745-45-8 ]
[ 1160853-86-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 2121 - 2124

26
[ 17745-45-8 ]
[ 959617-32-4 ]
C₉H₁₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate;palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 100℃; for 6h;	1.5 g of 4-oxo-6-(tetrahydropyran-2-yloxymethyl)-4H-pyran-3-yl trifluoromethane-sulfonate were dissolved in 40 ml of toluene, and 47 mg of palladium(II) acetate, 260 mg of BINAP, 2.73 g of cesium carbonate and 442 mg of n-<strong>[17745-45-8]propylboronic acid</strong> were added. The reaction mixture was heated at 100 C. for 6 h. The solids were filtered off, and the reaction mixture was concentrated on a rotary evaporator. The crude product was purified by flash chromatography (mobile phase: ethyl acetate/heptane) and then dissolved in 20 ml of acetonitrile, and 2.7 ml of a solution of 25 g of CrO3 and 25 ml of H2SO4 in 100 ml of water were added. After 1 h, 100 ml of methyl tert-butyl ether were added to the reaction solution. The reaction solution was then extracted twice with in each case 30 ml of a 1-molar HCl solution. The organic phase was dried over magnesium sulfate and concentrated on a rotary evaporator. The crude product was then purified by HPLC (Agilent-Prep.-C18, mobile phase MeCN/H2O/TFA). This gave 194 mg (1.07 mmol) of 5-propyl-4-oxo-4H-pyran-2-carboxylic acid as a colorless solid. LCMS: m=183.09 (M+H)+.

Reference： [1]Patent: US2010/144862,2010,A1 .Location in patent: Page/Page column 24

27
[ 67-56-1 ]
[ 17745-45-8 ]
[ 121-43-7 ]
[ 2938-87-6 ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 803 - 805

28
[ 17745-45-8 ]
[ 769-92-6 ]
N-(4-tert-butylphenyl)-N-propylamine [ No CAS ]

Reference： [1]Synlett,2010,p. 2101 - 2105

29
[ 17745-45-8 ]
[ 106-47-8 ]
[ 73938-86-0 ]

Reference： [1]Synlett,2010,p. 2101 - 2105

30
[ 17745-45-8 ]
[ 104-94-9 ]
[ 71193-47-0 ]

Reference： [1]Synlett,2010,p. 2101 - 2105

31
[ 17745-45-8 ]
C₉H₇BrFN₃ [ No CAS ]
C₁₂H₁₄FN₃ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 2732 - 2735

32
[ 17745-45-8 ]
[ 1338684-64-2 ]
[ 1338684-88-0 ]

Yield	Reaction Conditions	Operation in experiment
48%	With potassium fluoride; caesium carbonate;bis(tri-t-butylphosphine)palladium(0); In 1,4-dioxane; at 100℃; for 24h;Inert atmosphere;	To an N2 flushed 40 mL vial containing 5-chloro-4-methyl-2-nitro-N-(3- phenylpropyl)aniline (0.355 g, 1.1 mmol) and 1,4-dioxane (25 mL) is added Cs2C03 (1.82 g, 5.5 mmol), KF (0.254 g, 4.4 mmol), <strong>[17745-45-8]propylboronic acid</strong> (0.392 g, 4.5 mmol), and bis(tri-tert-butylphosphine)palladium(0) (0.096 g, 0.18 mmol). The reaction mixture is shaken at 100 C for 24 h. The mixture is cooled to rt and filtered through a silica gel column (2x4 cm), using DCM (50 mL). The filtrate is concentrated and chromatographed on silica gel (4x14 cm column, using a gradient from heptane to 20% DCM/heptane) to provide 165 mg (48%) of 4-methyl-2-nitro-N-(3-phenylpropyl)-5-propylaniline as a red oil. MS (ESI+) for Ci9H24N202 m/z 313.3 (M+H)+.

Reference： [1]Patent: WO2011/126567,2011,A1 .Location in patent: Page/Page column 227

33
[ 17745-45-8 ]
[ 17763-80-3 ]
[ 10342-59-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 1397 - 1401

34
[ 17745-45-8 ]
[ 4923-84-6 ]
C₂₈H₆₄B₄O₁₂P₄ [ No CAS ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 9939 - 9945

35
[ 924-44-7 ]
[ 17745-45-8 ]
[ 88945-70-4 ]

Yield	Reaction Conditions	Operation in experiment
23%	With [Rh(OH)(cod)]2; (4aR,9aR)-6,8-dibenzyl-2,3-dimethoxy-2,3-dimethyl-3,4a,5,8,9,9a-hexahydro-2H-[1,4]dioxino[2,3-e][1,3]diazepin-6-ium hexafluorophosphate; potassium tert-butylate; In tert-Amyl alcohol; toluene; at 20℃; for 4h;Inert atmosphere;	General procedure: [Rh(I)]2 (1.5 mol %, 7.34×10-3 mmol) or [Rh(I)] (3 mol %, 0.015 mmol) was added to a round bottom flask, under an inert atmosphere. NHC precursor (3.3 mol %, 0.015 mmol), arylboronic acid or derivative (2 equiv, 0.98 mmol), KOtBu (1 equiv, 0.49 mmol) and solvent (2 ml) were added sequentially. Finally, ethyl glyoxalate (50% in toluene, 0.49 mmol, 100 mul) was added and the reaction was stirred at the desired temperature, and monitored by TLC. The crude mixture was passed through a porous ceramic glass filter and eluted with CH2Cl2. The solvents were concentrated under reduced pressure and the residue purified by liquid chromatography (SiO2 gel, Hexane/AcOEt (5/1)), yielding the desire alpha-hydroxyester product.
< 10%	With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; C18H30N4O4(2+)*2Cl(1-); potassium tert-butylate; In tert-Amyl alcohol; toluene; at 60℃; for 4h;Inert atmosphere;	General procedure: At first, [Rh(I)]2 (1.5 mol %, 7.34 103 mmol) or [Rh(I)] (3 mol %, 0.015 mmol) was added to a round bottom flask, underan inert atmosphere. Next, the NHC precursor (3.3 mol %,0.015 mmol), arylboronic acid or derivative (2 equiv, 0.98 mmol),KOtBu (1 equiv, 0.49 mmol), and solvent (2 ml) were added sequentially. Finally, ethyl glyoxalate (50% in toluene, 0.49 mmol,100 ll) was added and the reaction was stirred at the desired temperature,and monitored by TLC. The crude mixture was passed through a porous ceramic glass filter and eluted with CH2Cl2. The solvents were concentrated under reduced pressure and the residue purified by liquid chromatography (SiO2 gel, Hexane/AcOEt(5/1)), yielding the desired ethyl mandelate product.

Reference： [1]Tetrahedron,2012,vol. 68,p. 7211 - 7216
[2]Tetrahedron Asymmetry,2013,vol. 24,p. 628 - 632

36
[ 17745-45-8 ]
[ 671795-60-1 ]
[ 1422021-95-1 ]

Yield	Reaction Conditions	Operation in experiment
100 mg	With palladium diacetate; potassium carbonate; ruphos; In water; toluene; at 120℃; for 0.333333h;Inert atmosphere; Microwave irradiation;	Step (b): 2-amino-5-bromo-4-chlorobenzonitrile (212 mg, 0.92 mmol), <strong>[17745-45-8]propylboronic acid</strong> (80.5 mg, 0.92 mmol), Pd(OAc)2 (10.3 mg, 0.05 mmol), RuPhos (42.7 mg, 0.09 mmol) andK2C03 (633 mg, 4.6 mmol) were mixed in toluene /water (3 mL, 10:1) under nitrogen. The reaction mixture was heated in microwave at 120 C for 20 min. H20 was added and the aqueous mixture was extracted with DCM and EtOAc. The combined organic phases were filtered through a phase separator and the solvent was evaporated under reduced pressure. The crude product was purified on preparative HPLC. 100 mg 2-amino-4-chloro-5- propylbenzonitrile was obtained.
100 mg	With palladium diacetate; potassium carbonate; ruphos; In water; toluene; at 120℃; for 0.333333h;Inert atmosphere; Microwave irradiation;	Step (b): 2-amino-5-bromo-4-chlorobenzonitrile (212 mg, 0.92 mmol), <strong>[17745-45-8]propylboronic acid</strong> (80.5 mg, 0.92 mmol), Pd(OAc)2 (10.3 mg, 0.05 mmol), RuPhos (42.7 mg, 0.09 mmol) and K2CO3 (633 mg, 4.6 mmol) were mixed in toluene/water (3 mL, 10:1) under nitrogen. The reaction mixture was heated in microwave at 120 C. for 20 min. H2O was added and the aqueous mixture was extracted with DCM and EtOAc. The combined organic phases were filtered through a phase separator and the solvent was evaporated under reduced pressure. The crude product was purified on preparative HPLC. 100 mg 2-amino-4-chloro-5-propylbenzonitrile was obtained.

Reference： [1]Patent: WO2013/17654,2013,A1 .Location in patent: Page/Page column 31
[2]Patent: US2014/323518,2014,A1 .Location in patent: Paragraph 0127

37
[ 17745-45-8 ]
[ 39263-32-6 ]
[ 1422021-93-9 ]

Yield	Reaction Conditions	Operation in experiment
17.1 mg	With palladium diacetate; potassium carbonate; ruphos; In water; toluene; at 140℃; for 0.333333h;Inert atmosphere; Microwave irradiation;	Synthesis of Intermediate A (a) Propylboronic acid, KzC03, PdOAc2, RuPhos, toluene/ H20; (b) 12, AgS04, EtOH. Scheme 1 Step (a): 2-amino-5-bromobenzonitrile (25 mg, 0.13 mmol), <strong>[17745-45-8]propylboronic acid</strong> (78.08 mg, 0.89 mmol), Pd(OAc)2 (5.70 mg, 0.03 mmol), RuPhos (23.68 mg, 0.05 mmol) and K2C03 (87.68 mg, 0.63 mmol) were mixed in toluene /water (2 mL, 10: 1) under nitrogen. The reaction mixture was heated in microwave at 140 C for 20 min, cooled to room temperature and filtered through celite. The solvent was evaporated under reduced pressure and the crude product was purified on silica using EtOAc/n-heptane (10 - 20 % EtOAc) as mobile phase. 17.1 mg 2-amino-5-propylbenzonitrile was obtained as yellowish oil.
17.1 mg	With palladium diacetate; potassium carbonate; ruphos; In water; toluene; at 140℃; for 0.333333h;Inert atmosphere; Microwave irradiation;	Step (a): 2-amino-5-bromobenzonitrile (25 mg, 0.13 mmol), <strong>[17745-45-8]propylboronic acid</strong> (78.08 mg, 0.89 mmol), Pd(OAc)2 (5.70 mg, 0.03 mmol), RuPhos (23.68 mg, 0.05 mmol) and K2CO3 (87.68 mg, 0.63 mmol) were mixed in toluene/water (2 mL, 10:1) under nitrogen. The reaction mixture was heated in microwave at 140 C. for 20 min, cooled to room temperature and filtered through celite. The solvent was evaporated under reduced pressure and the crude product was purified on silica using EtOAc/n-heptane (10-20% EtOAc) as mobile phase. 17.1 mg 2-amino-5-propylbenzonitrile was obtained as yellowish oil.

Reference： [1]Patent: WO2013/17654,2013,A1 .Location in patent: Page/Page column 30-31
[2]Patent: US2014/323518,2014,A1 .Location in patent: Paragraph 0123

38
[ 17745-45-8 ]
[ 181998-06-1 ]
[ 1426385-53-6 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 2218 - 2234

39
[ 444343-55-9 ]
[ 17745-45-8 ]
[ 644-36-0 ]
2-(methyl)-6-(n-butyl)phenylacetic acid [ No CAS ]
2-(methyl)-6-(n-propyl)phenylacetic acid [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 17508 - 17513

40
[ 17745-45-8 ]
[ 644-36-0 ]
2-(methyl)-6-(n-propyl)phenylacetic acid [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 17508 - 17513

41
[ 17745-45-8 ]
[ 1569843-16-8 ]
[ 1569843-13-5 ]

Yield	Reaction Conditions	Operation in experiment
156 mg		Intermediate P44 was converted to 3-cyano-4-(pyridin-4-yl)-6,7, 8 ,9-tetrahydro-5H- cyclohepta[b]pyridin-2-yl trifluoromethanesulfonate using General Method 5, step 1. 3-Cyano-4- (pyridin-4-yl)-6,7, 8 ,9-tetrahydro-5H-cyclohepta[b]pyridin-2-yl trifluoromethanesulfonate (1096mg), n-<strong>[17745-45-8]propylboronic acid</strong> (727 mg) and potassium phosphate tribasic (1.79 g) were combined with toluene (34.4 ml), molsieves (4 A) were added and the mixture was stirred at room temperature for 5 mm. (1,3 -Diisopropylimidazo l-2-ylidene)(3 -chloropyridyl)palladium(II) dichloride (PEPPSI) (150 mg) was added and the reaction mixture was heated to 100C for 52 h. (1,3 -Diisopropylimidazo l-2-ylidene)(3 -chloropyridyl)palladium(II) dichloride (150 mg) wasadded and stirring at 100 C was continued for 24 h. The reaction mixture was filtered with EtOAc and water through glass fiber paper, then it was extracted with EtOAc, the organic phases were washed with water and brine, dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 50 g, 5% to 60% EtOAc in n-heptane) to give the title compound (156 mg) as an off-white solid. MS (ESP): m/z = 292.4 [M+H].

Reference： [1]Patent: WO2014/29723,2014,A1 .Location in patent: Page/Page column 170

42
[ 17745-45-8 ]
[ 1593700-02-7 ]
[ 1593700-05-0 ]

Yield	Reaction Conditions	Operation in experiment
		Example 8-04 [0351] To a mixture of Example 8-02 (150 mg) and toluene (7 mL) under argon was added a suspension of <strong>[17745-45-8]propylboronic acid</strong>, cesium carbonate and toluene (7 mL). After 30 minutes Pd(PPh3)4 (15 mg) was added and the mixture heated to 95 C. for 12 hours. After cooling to r.t. HCl (1 N) was added and the mixture diluted with EA. The organic layer was washed with sodium bicarbonate solution and filtered over a short pad of silica gel. The filtrate was concentrated and the residue purified by HPLC to provide Example 8-04.
	With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In toluene; at 95℃; for 12h;Inert atmosphere;	To a mixture of Example 8-02 (150 mg) and toluene (7 mL) under argon was added a suspension of <strong>[17745-45-8]propylboronic acid</strong>, cesium carbonate and toluene (7 mL). After 30 minutes Pd(PPh3) (15 mg) was added and the mixture heated to 95C for 12 hours. After cooling to r.t. HCI (1 N) was added and the mixture diluted with EA. The organic layer was washed with sodium bicarbonate solution and filtered over a short pad of silica gel. The filtrate was concentrated and the residue purified by HPLC to provide Example 8-04.

Reference： [1]Patent: US2014/99333,2014,A1 .Location in patent: Paragraph 0347; 0350; 0351
[2]Patent: WO2014/56938,2014,A1 .Location in patent: Page/Page column 74

43
[ 78105-37-0 ]
[ 17745-45-8 ]
[ 1643786-49-5 ]

Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 7245 - 7248

44
[ 17745-45-8 ]
[ 4131-43-5 ]
C₁₉H₃₀Si [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 5799 - 5805

45
[ 17745-45-8 ]
tert-butyl N-[5-bromo-6-(3,4-dichlorophenoxymethyl)-1,2-benzoxazol-3-yl]-N-[(tertbutoxy)carbonyl]carbamate [ No CAS ]
tert-butyl N-[(tert-butoxy)carbonyl]-N-[6-(3,4-dichlorophenoxymethyl)-5-propyl-1,2-benzoxazol-3-yl]carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
27%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium fluoride; In 1,4-dioxane; water; at 90℃; for 16h;	To the mixture of tert-butyl N-[5-bromo-6-(3,4-dichlorophenoxymethyl)-l,2-benzoxazol-3-yl]-N-[(tert-butoxy)carbonyl]carbamate (200 mg, 0.34 mmol) and <strong>[17745-45-8]propylboronic acid</strong> (60 mg, 0.68 mmol) in dioxane (6 mL) and H20 (0.3 mL) was added [1,1'-Bis(diphenylphosphino)ferrocene]palladium(II) chloride (42 mg, 0.05 mmol) and cesium fluoride (180 mg, 1.19 mmol). After stirring at 90 C for 16 h, the mixture was filtered through celite and the filtrate was concentrated. The residue was purified by reverse phase combiflash (20%-50% CH3CN/ H2O in 0.1% NH4HCO3) to give oil product (50 mg, 27%). LCMS (ESI) m/z: 395.0 [M-156+H]+.

Reference： [1]Patent: WO2014/144545,2014,A2 .Location in patent: Page/Page column 60; 61

46
[ 17745-45-8 ]
[ 106-51-4 ]
[ 55811-48-8 ]

Yield	Reaction Conditions	Operation in experiment
41%	With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; In dichloromethane; water; at 20℃; for 12h;	General procedure: To a solution of benzoquinone (0.5 mmol, 1.0 equiv.) and [Cp*IrCl2]2 (0.025mmol, 5%) in dichloromethane (2 mL) was added the phenylboronic acid (0.75 mmol, 1.5 equiv.) and water (2 mL) Then the solution was stirred vigorously at room temperature for 12 h. Upon completion, the reaction was diluted with dichloromethane (5 mL) and washed with 5% sodium bicarbonate. The layers were separated, and the aqueous layer was extracted with dichloromethane (10 X 3 mL), dried over sodium sulfate, and was evaporated to give the residue. The residue was then purified by column chromatography on silica gel (ethyl acetate / petroleumether = 1:10) to provide the corresponding product.

Reference： [1]Journal of Organometallic Chemistry,2015,vol. 780,p. 30 - 33

47
[ 17745-45-8 ]
[ 130-15-4 ]
[ 34491-84-4 ]

Yield	Reaction Conditions	Operation in experiment
35%	With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; In dichloromethane; water; at 20℃; for 12h;	General procedure: To a solution of benzoquinone (0.5 mmol, 1.0 equiv.) and [Cp*IrCl2]2 (0.025mmol, 5%) in dichloromethane (2 mL) was added the phenylboronic acid (0.75 mmol, 1.5 equiv.) and water (2 mL) Then the solution was stirred vigorously at room temperature for 12 h. Upon completion, the reaction was diluted with dichloromethane (5 mL) and washed with 5% sodium bicarbonate. The layers were separated, and the aqueous layer was extracted with dichloromethane (10 X 3 mL), dried over sodium sulfate, and was evaporated to give the residue. The residue was then purified by column chromatography on silica gel (ethyl acetate / petroleumether = 1:10) to provide the corresponding product.

Reference： [1]Journal of Organometallic Chemistry,2015,vol. 780,p. 30 - 33

48
[ 17745-45-8 ]
tert-butyl 9-bromo-7,7-dimethyl-3,4,6,7-tetrahydro[1,4]diazepino[6,7,1-hi]indole-2(1H)-carboxylate [ No CAS ]
tert-butyl 7,7-dimethyl-9-propyl-3,4,6,7-tetrahydro[1,4]diazepino[6,7,1-hi]indole-2(1H)-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate; In 1,4-dioxane; at 80℃; for 15h;	To a mixture of tert-butyl 9-bromo-7,7-dimethyl-3,4,6,7-tetrahydro-[l,4]diazepino[6,7,l-hi]indole-2(lH)-carboxylate (20 mg, 52.45 muiotaetaomicron), <strong>[17745-45-8]propylboronic acid</strong> (6.917 mg, 78.68 muiotaetaomicron), potassium phosphate (27.83 mg, 0.131 mmol), and palladium (II) acetate (706.5 mug, 3.1 muiotaetaomicron) in dioxane (0.5 mL) was added S-phos (2.153 mg, 5.2 muiotaetaomicron). The reaction was stirred at 80 C for 15 h. The mixture was filtered through a syringe filter. The filtrate was purified by preparative HPLC to give tert-butyl 7,7-dimethyl-9-propyl-3,4,6,7-tetrahydro-[l,4]diazepino[6,7,l- i;]indole-2(lH)-carboxylate.

Reference： [1]Patent: WO2015/66344,2015,A1 .Location in patent: Page/Page column 221

49
[ 17745-45-8 ]
2-bromo-5-((3-fluoropyridin-2-yl)methoxy)nitrobenzene [ No CAS ]
3-fluoro-2-((3-nitro-4-propylphenoxy)methyl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.2 g	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In tetrahydrofuran; for 9h;Reflux;	To a solution of 2-((4-bromo-3-nitrophenoxy)methyl)-3-fluoropyridine (1.5 g), n-<strong>[17745-45-8]propylboronic acid</strong> (0.8 g), potassium carbonate (1.9 g) and iron oxide(I) (2.7 g) in THF (30 mL) was added 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride-dichloromethane complex (0.7 g) at room temperature. The reaction mixture was stirred under reflux for 9 hr, and the insoluble material was filtered off by using celite. Water was added to the filtrate, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.2 g). MS (ESI+): [M+H]+291.4.

Reference： [1]Patent: EP2889291,2015,A1 .Location in patent: Paragraph 0743

50
[ 17745-45-8 ]
[ 98495-32-0 ]
3-propyl-5-(3-pyridyl)-2,4-dihydro-1,2,4,3-triazaborole [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 74 - 77

51
[ 17745-45-8 ]
naphthalen-1-yl 2,3,4,5,6-pentafluorobenzenesulfonate [ No CAS ]
[ 2765-18-6 ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium phosphate monohydrate; palladium diacetate; XPhos; In tert-butyl alcohol; at 50℃; for 12h;Schlenk technique; Inert atmosphere; Sealed tube;	General procedure: Procedure A: To a Schlenk tube equipped with a magnetic stiring bar and a teflon septum was charged K3PO4.H2O (1.5 mmol, 3 equiv), aryl pentafluorobenzene sulfonate (0.5 mmol, 1.0 equiv), aryl boronic acid (0.75 mmol, 1.5 equiv) and Pd(PPh3)2Cl2 (0.015 mmol, 3 mol%). The tube was then capped with a rubber septum, evacuated and backfilled with nitrogen and this cycle was repeated twice. Under an inertatmosphere, tert - butanol (3 mL) was added via syringe. Under a positive pressure of nitrogen, the rubber septum was replaced with a Teflon screw cap and this was sealed. The Schlenk tube was stirred at room temperature for the time indicated. When the reaction was completed according to TLC or GCMS (FID), thereaction mixture was diluted with EtOAc (5 mL) and filtered through celite bed. The organic layer was concentrated under reduced pressure. The residue was purified through silica gel (230 - 400 mesh) column chromatography using 1-10% ethyl acetate in petroleum ether to afford the product. Procedure B: Similar procedure as A except that Pd(OAc)2 (3 mol%) and Xphos (5 mol%) instead of Pd(PPh3)2Cl2 as catalyst system.

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 5106 - 5111

52
[ 17745-45-8 ]
[ 1158680-89-7 ]
7-propyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 1080 - 1085

53
[ 103-82-2 ]
[ 17745-45-8 ]
phenylacetic acid [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 11946 - 11949

54
[ 17745-45-8 ]
[ 1395898-00-6 ]
C₁₈H₂₄AuB₂NO₃ [ No CAS ]

Reference： [1]Chemical Communications,2015,vol. 51,p. 15800 - 15803

55
[ 17745-45-8 ]
N'-(cyclohexylmethyl)-N'-((1R,2S,E)-1-hydroxy-1,4-diphenylbut-3-en-2-yl)-4-methoxybenzohydrazide [ No CAS ]
(7S,8R,Z)-6-(cyclohexylmethyl)-4-(4-methoxyphenyl)-8-phenyl-2-propyl-7-((E)-styryl)-7,8-dihydro-6H-1,3,5,6,2-dioxadiazaborocine [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 8395 - 8397
Angew. Chem.,2015,vol. 127,p. 8515 - 8517,7

56
[ 17745-45-8 ]
[ 400749-87-3 ]
3'-propylbiphenyl-4-ylcarbaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With potassium phosphate; palladium diacetate; catacxium A; In water; toluene; at 100℃; for 3h;Inert atmosphere;	To a solution of 500 mg (1.91 mmol) of 3?-bromobiphenyl-4-ylcarbaldehyde in 28 mL of toluene were added1.7 mL of water, 1.63 g (7.68 mmol) of tripotassium phosphate, and 675 mg (7.68 mmol) of <strong>[17745-45-8]propylboronic acid</strong>, degassedunder reduced pressure, and then substituted with nitrogen gas. Thereafter, 6.2 mg (0.028 mmol) of palladium acetateand 20.2 mg (0.0563 mmol) of butyl-di-1-adamantylphosphine were added and stirred for 3 hours at 100C in a nitrogengas atmosphere. The post-treatment after the completion of the reaction was performed in accordance with ReferenceExample 5 to afford 406 mg of the title compound as a pale yellow oil. (Yield: 86%)Mass spectrum (EI, m/z): 224 (M+)1H-NMR spectrum (CDCl3, delta ppm): 10.06 (s, 1H), 7.99-7.91 (m, 2H), 7.78-7.73 (m, 2H), 7.51-7.34 (m, 3H), 7.28-7.20(m, 1H), 2.73-2.61 (m, 2H), 1.80-1.62 (m, 2H), 0.98 (t, J = 7.3 Hz, 3H)
86%	With potassium phosphate; palladium diacetate; catacxium A; In water; toluene; at 100℃; for 3h;Inert atmosphere;	3'-bromobiphenyl-4-yl carbaldehyde in 28mL of toluene solution of the 500mg (1.91mmol), 1.7mL water, tripotassium phosphate 1.63g (7.68mmol) and propyl borate was added to 675mg (7.68mmol), reduced pressure after degassing, nitrogen gas was substituted. Subsequently, 6.2mg of palladium acetate (0.028mmol) and butyl-di-1-adamantyl phosphine added to the pin 20.2mg (0.0563mmol) and, in a nitrogen gas atmosphere, was stirred for 3 hours at 100 . After completion of the reaction after the treatment is carried out to obtain a junseo, 406mg title compound in Reference Example 5 as a light yellow oil (yield: 86%)
	With tricalcium diphosphate; palladium diacetate; catacxium A; In water; toluene; at 100℃; for 3h;Inert atmosphere;	Comparative Example 1 {6-[(3'-Propylbiphenyl-4-ylmethyl)(pyridin-2-ylsulfonyl)aminomethyl]pyridin-2-ylamino}acetate This compound is the compound of Example Number 754 of WO2009/113600. [0135]1-(a): 3'-Propylbiphenyl-4-ylcarbaldehyde 1.7 mL of water, 1.63 g (7.68 mmol) of tricalcium phosphate and 675 mg (7.68 mmol) of <strong>[17745-45-8]propylboronic acid</strong> were added to 28 mL solution of toluene containing 500 mg (1.91 mmol) of 3'-bromobiphenyl-4-ylcarbaldehyde followed by degassing under reduced pressure and substituting with nitrogen gas. Next, 6.2 mg (0.028 mmol) of palladium acetate and 20.2 mg (0.0563 mmol) of butyl di-1-adamantylphosphine were added followed by stirring for 3 hours at 100 C. in a nitrogen gas atmosphere. Post-treatment following completion of the reaction was performed in accordance with Reference Example 5 to obtain 406 mg of the title compound in the form of a pale yellow oil (yield: 86%). mass spectrum (EI, m/z): 224 (Mr). 1H-NMR spectrum (CDCl3, delta ppm): 10.06 (s, 1H), 7.99-7.91 (m, 2H), 7.78-7.73 (m, 2H), 7.51-7.34 (m, 3H), 7.28-7.20 (m, 1H), 2.73-2.61 (m, 2H), 1.80-1.62 (m, 2H), 0.98 (t, J=7.3 Hz, 3H).

Reference： [1]Patent: EP2980075,2016,A1 .Location in patent: Paragraph 0150
[2]Patent: KR2015/135460,2015,A .Location in patent: Paragraph 0380; 0381; 0383; 0384
[3]Patent: US2016/213657,2016,A1 .Location in patent: Paragraph 0285

57
[ 17745-45-8 ]
C₂₂H₂₀ClN₅O₂ [ No CAS ]
1-{3-methyl-2-[2-methyl-4-(6-propylpyridin-3-yl)phenoxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.06 g	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; cesium fluoride; In 1,4-dioxane; at 80℃; for 6h;	Production Example 16 (1058) A mixture of 0.10 g of the present compound 37, 0.04 g of <strong>[17745-45-8]propylboronic acid</strong>, 0.01 g of [1,1?-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct, 0.13 g of cesium fluoride, and 6 mL of 1,4-dioxane was stirred at 80 C. for 6 hours. After cooling, the reaction mixture was concentrated and the residue thus obtained was subjected to silica gel column chromatography to obtain 0.06 g of 1-{3-methyl-2-[2-methyl-4-(6-propylpyridin-3-yl)-phenoxymethyl]-phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 126). (1059) 1H-NMR (CDCl3) delta: 1.01 (3H, t, J=7.4 Hz), 1.80-1.85 (2H, m), 2.17 (3H, s), 2.53 (3H, s), 2.82 (2H, t, J=7.7 Hz), 3.64 (3H, s), 5.10 (2H, s), 6.92 (1H, d, J=8.2 Hz), 7.03 (1H, d, J=7.7 Hz), 7.28-7.31 (1H, m), 7.41-7.47 (3H, m), 7.61 (1H, t, J=7.7 Hz), 7.74-7.79 (2H, m).

Reference： [1]Patent: US2016/150787,2016,A1 .Location in patent: Paragraph 1058-1059

58
[ 611-35-8 ]
[ 17745-45-8 ]
C₁₂H₁₂ClN [ No CAS ]