[ CAS No. 14559-88-7 ] {[proInfo.proName]}

Name: 14559-88-7|(2-Methylprop-1-en-1-yl)boronic acid|96%
Brand: Ambeed
SKU: A285793
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Quality Control of [ 14559-88-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 14559-88-7 ]

SDS Specification

Alternatived Products of [ 14559-88-7 ]

Product Details of [ 14559-88-7 ]

CAS No. :	14559-88-7	MDL No. :	MFCD01074609
Formula :	C₄H₉BO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FWJRSOGVYOIVOC-UHFFFAOYSA-N
M.W :	99.92	Pubchem ID :	2763299
Synonyms :

Calculated chemistry of [ 14559-88-7 ]

Physicochemical Properties

Num. heavy atoms :	7
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.5
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	30.0
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) :	-6.32 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	0.83
Log Po/w (WLOGP) :	-0.04
Log Po/w (MLOGP) :	-0.33
Log Po/w (SILICOS-IT) :	-1.69
Consensus Log Po/w :	-0.24

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.92
Solubility :	12.1 mg/ml ; 0.121 mol/l
Class :	Very soluble
Log S (Ali) :	-1.26
Solubility :	5.46 mg/ml ; 0.0547 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	0.44
Solubility :	278.0 mg/ml ; 2.78 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.19

Safety of [ 14559-88-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 14559-88-7 ]

* 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 [ 14559-88-7 ]

[ 14559-88-7 ] Synthesis Path-Downstream 1~88

1
[ 121-43-7 ]
[ 29917-94-0 ]
[ 14559-88-7 ]

Reference： [1]Journal of Organic Chemistry,1953,vol. 18,p. 895
[2]Journal of Organic Chemistry,1953,vol. 18,p. 895
[3]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: B: B-Verb.13, 4.7.2.2, page 189 - 196

2
[ 14559-88-7 ]
[ 107-21-1 ]
[ 14560-03-3 ]

Reference： [1]Bulletin de la Societe Chimique de France,1966,p. 2557 - 2564

3
[ 14559-88-7 ]
[ 71-36-3 ]
[ 14559-93-4 ]

Reference： [1]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1959,vol. 248,p. 828
[2]Bulletin de la Societe Chimique de France,1966,p. 2557 - 2564

4
[ 121-43-7 ]
[ 38614-36-7 ]
[ 14559-88-7 ]

Reference： [1]Bulletin de la Societe Chimique de France,1966,p. 2557 - 2564
[2]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: B: B-Verb.13, 4.7.2.2, page 189 - 196

5
[ 59278-44-3 ]
[ 67-64-1 ]
[ 14559-88-7 ]

Reference： [1]Journal of the American Chemical Society,1975,vol. 97,p. 5608 - 5609

6
[ 14559-88-7 ]
[ 111-27-3 ]
[ 14559-98-9 ]

Reference： [1]Bulletin de la Societe Chimique de France,1966,p. 2557 - 2564

9
[ 121-43-7 ]
2-methyl-propenyl magnesium halide [ No CAS ]
[ 14559-88-7 ]

Reference： [1]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1959,vol. 248,p. 828

10
[ 14559-88-7 ]
[ 126-30-7 ]
[ 676593-25-2 ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 6098 - 6099
[2]Angewandte Chemie - International Edition,2015,vol. 54,p. 9293 - 9297
Angew. Chem.,2015,vol. 127,p. 9425 - 9429,5

11
[ 14559-88-7 ]
[ 103502-52-9 ]
C₁₅H₁₇BrO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	With N-benzyl-N,N,N-triethylammonium chloride; cesium fluoride;bis-triphenylphosphine-palladium(II) chloride; In water; toluene; at 20℃;	5-Benzyloxy-3,4-dihalo-5H-furan-2-one (1 equivalent), boronic acid (2 equivalents, cesium fluoride (2.5 equivalents, PdCl2(PPh3)2 (0.05 equivalent), and triethylbenzyl ammonium chloride (0.05 equivalent) were combined. To this mixture was added a nitrogen-purged toluene and water solvent mixture. The reaction mixture was stirred at room temperature over night and then quenched with 2N aqueous HCl and extracted with 100 mL toluene. The extract was concentrated in vacuo to provide the crude product as a pale orange oil which was purified by column chromatography on silica gel eluting with 10% ethyl acetate in heptane. [0124] 2. 5-Benzyloxy-3-bromo-4-isopropyl-5H-furan-2-one. 30% yield. MS (AP+) 325.0.

Reference： [1]Patent: US2003/225149,2003,A1 .Location in patent: Page 15

12
[ 1046793-45-6 ]
[ 14559-88-7 ]
1-Benzenesulfonyl-3-[2-(1-methyl-piperidin-4-yl)-thiazol-4-yl]-5-(2-methyl-propenyl)-1H-pyrrolo[2,3-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With sodium carbonate; lithium chloride;bis-triphenylphosphine-palladium(II) chloride; In ethanol; water; toluene;Heating / reflux;	1-Benzenesulfonyl-3-[2-(1-methyl-piperidin-4-yl)-thiazol-4-yl]-5-(2-methyl-propenyl)-1H-pyrrolo[2,3-b]pyridine (75) To a stirred solution of 74 (202 mg, 0.39 mmol), isobutenyl boronic acid (50 mg, 0.50 mmol) and (PPh3)2PdCl2 (30 mg, 43 mumol) in toluene:EtOH 1:1 (3 mL) was added LiCl (50 mg, 1.19 mmol) and 1.0 M aq. Na2CO3 (0.75 mL, 0.75 mmol). The mixture was heated to reflux (bath temperature 110C) and stirred for 1.5 h. Saturated aqueous NaHCO3 (25 mL) was added, and the mixture was extracted with AcOEt (2 x 40 mL). The combined organic solutions were dried (MgSO4) and concentrated to afford a brown solid (255 mg). The crude product was purified by SGC with 5%MeOH in CH2Cl2 as eluent to afford 75 as an off-white powder (166 mg, 0.34 mmol, 86%). 1H NMR (400 MHz, CDCl3) delta 1.88 (s, 3H), 1.96 (s, 3H), 1.92-2.04 (m, 2H), 2.11-2.25 (m, 2H), 2.37 (s, 3H), 2.97-3.11 (m, 3H), 6.33 (1H, s, 1H), 7.34 (s, 1H), 7.48 (t, J = 7.5 Hz, 2H), 7.54-7.60 (m, 1H), 8.14 (s, 1H), 8.20-8.25 (m, 3H), 8.36 (d, J = 2.0 Hz, 1H).
86%	With sodium carbonate; lithium chloride;bis-triphenylphosphine-palladium(II) chloride; In ethanol; water; toluene; at 110℃; for 1.5h;	1-Benzenesulfonyl-3-[2-(1-methyl-piperidin-4-yl)-thiazol-4-yl]-5-(2-methyl-propenyl)-1H-pyrrolo[2,3-b]pyridine (75) To a stirred solution of 74 (202 mg, 0.39 mmol), isobutenyl boronic acid (50 mg, 0.50 mmol) and (PPh3)2PdCl2 (30 mg, 43 mumol) in toluene:EtOH 1:1 (3 mL) was added LiCl (50 mg, 1.19 mmol) and 1.0 M aq. Na2CO3 (0.75 mL, 0.75 mmol). The mixture was heated to reflux (bath temperature 110 C.) and stirred for 1.5 h. Saturated aqueous NaHCO3 (25 mL) was added, and the mixture was extracted with AcOEt (2*40 mL). The combined organic solutions were dried (MgSO4) and concentrated to afford a brown solid (255 mg). The crude product was purified by SGC with 5% MeOH in CH2Cl2 as eluent to afford 75 as an off-white powder (166 mg, 0.34 mmol, 86%). 1H NMR (400 MHz, CDCl3) delta 1.88 (s, 3H), 1.96 (s, 3H), 1.92-2.04 (m, 2H), 2.11-2.25 (m, 2H), 2.37 (s, 3H), 2.97-3.11 (m, 3H), 6.33 (1H, s, 1H), 7.34 (s, 1H), 7.48 (t, J=7.5 Hz, 2H), 7.54-7.60 (m, 1H), 8.14 (s, 1H), 8.20-8.25 (m, 3H), 8.36 (d, J=2.0 Hz, 1H).

Reference： [1]Patent: EP1749829,2007,A1 .Location in patent: Page/Page column 69; 71
[2]Patent: US2007/72896,2007,A1 .Location in patent: Page/Page column 68

13
[ 1046793-41-2 ]
[ 14559-88-7 ]
4-[1-Benzenesulfonyl-5-(2-methyl-propenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-thiazole-2-carboxylic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With sodium carbonate; lithium chloride;bis-triphenylphosphine-palladium(II) chloride; In ethanol; water; toluene; at 110℃; for 1.5h;Heating / reflux;	4-[1-Benzenesulfonyl-5-(2-methyl-propenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-thiazole-2-carboxylic acid ethyl ester (80) To a stirred solution of 79 (683 mg, 1.55 mmol), isobutenyl boronic acid (180 mg, 1.81 mmol) and (PPh3)2PdCl2 (100 mg, 142 mumol) in toluene:EtOH 1:1 (10 mL) was added LiCl(160 mg, 3.81 mmol) and 1.0 M aqueous Na2CO3 (2.5 mL). The mixture was heated to reflux (bath temperature 110C) and stirred for 1.5 h. Saturated aqueous NaHCO3 (50 mL) was added, and the mixture was extracted with EtOAc (2 x 75 mL). The combined organic solutions were dried (MgSO4) and concentrated to afford a brown solid (922 mg). The crude product was isolated by means of SGC using hexane:EtOAc:CH2Cl2=2:1:1 (v/v/v) as eluent to afford 80 as a foam (548 mg, 1.32 mmol, 85%). 1H NMR (400 MHz, CDCl3) delta 1.40 (t, J = 7.2 Hz, 3H), 1.80 (d, J = 1.1 Hz, 3H), 1.86 (d, J = 1.1 Hz, 3H), 4.43 (q, J = 7.1 Hz, 2H), 6.24 (s, 1H), 7.40 (t, J = 7.8 Hz, 2H), 7.49 (t, J = 7.4 Hz, 1H), 7.63 (s, 1H), 8.13-8.17 (m, 3H)), 8.18 (s, 1H), 8.28 (d, J = 1.9 Hz, 1H).
85%	With sodium carbonate; lithium chloride;bis-triphenylphosphine-palladium(II) chloride; In ethanol; water; toluene; at 110℃; for 1.5h;	4-[1-Benzenesulfonyl-5-(2-methyl-propenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-thiazole-2-carboxylic acid ethyl ester (80) To a stirred solution of 79 (683 mg, 1.55 mmol), isobutenyl boronic acid (180 mg, 1.81 mmol) and (PPh3)2PdCl2 (100 mg, 142 mumol) in toluene:EtOH 1:1 (10 mL) was added LiCl(160 mg, 3.81 mmol) and 1.0 M aqueous Na2CO3 (2.5 mL). The mixture was heated to reflux (bath temperature 110 C.) and stirred for 1.5 h. Saturated aqueous NaHCO3 (50 mL) was added, and the mixture was extracted with EtOAc (2*75 mL). The combined organic solutions were dried (MgSO4) and concentrated to afford a brown solid (922 mg). The crude product was isolated by means of SGC-using hexane:EtOAc:CH2Cl2=2:1:1 (v/v/v) as eluent to afford 80 as a foam (548 mg, 1.32 mmol, 85%). 1H NMR (400 MHz, CDCl3) delta 1.40 (t, J=7.2 Hz, 3H), 1.80 (d, J=1.1 Hz, 3H), 1.86 (d, J=1.1 Hz, 3H), 4.43 (q, J=7.1 Hz, 2H), 6.24 (s, 1H), 7.40 (t, J=7.8 Hz, 2H), 7.49 (t, J=7.4 Hz, 1H), 7.63 (s, 1H), 8.13-8.17 (m, 3H)), 8.18 (s, 1H), 8.28 (d, J=1.9 Hz, 1H).

Reference： [1]Patent: EP1749829,2007,A1 .Location in patent: Page/Page column 73-74
[2]Patent: US2007/72896,2007,A1 .Location in patent: Page/Page column 70-71

14
[ 923584-11-6 ]
[ 14559-88-7 ]
[ 923583-88-4 ]

Yield	Reaction Conditions	Operation in experiment
45%	With sodium carbonate; lithium chloride;bis-triphenylphosphine-palladium(II) chloride; In ethanol; water; toluene; at 105℃; for 96h;	3-(1-methyl-1H-pyrazol-4-yl)-5-(2-methylprop-1-enyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (61) A mixture of bromide 37 (280 mg, 0.67 mmol), <strong>[14559-88-7]2,2-dimethylethenylboronic acid</strong> (101 mg, 1.01 mmol), LiCl (84 mg, 2.02 mmol), (PPh3)2PdCl2 (24 mg, 0.03 mmol), 1.0 M aqueous Na2CO3 (1.68 mL, 1.68 mmol), in toluene (8 mL) - EtOH (8 mL) was stirred in an oil bath (105 C) for 96 h. The reaction mixture was then cooled to r.t., diluted with AcOEt and saturated brine and partitioned. The aqueous layer was extracted with AcOEt (2x). The combined organic solutions were dried (MgSO4) and concentrated. The residual oil was purified by means of PTLC plates using AcOEt:hexane=1:1 (v/v) as eluent to afford the olefin 61 (118 mg, 45%) as an oil; 1H NMR (400 MHz; CDCl3) delta 1.88 (d, J = 1.0 Hz, 3H), 1.94 (d, J = 1.0 Hz, 3H), 3.96 (s, 3H), 6.37 (s, 1H), 7.39-7.46 (m, 3H), 7.49-7.54 (m, 1H), 7.59 (s, 1H), 7.63-7.68 (m, 2H), 7.75 (s, 1H), 7.90 (d, J = 1.8 Hz, 1H), 8.23 (d, J = 1.8 Hz, 1H).
45%	With sodium carbonate; lithium chloride;bis-triphenylphosphine-palladium(II) chloride; In ethanol; water; toluene; at 105℃; for 96h;	3-(1-methyl-1H-pyrazol-4-yl)-5-(2-methylprop-1-enyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (61) A mixture of bromide 37 (280 mg, 0.67 mmol), <strong>[14559-88-7]2,2-dimethylethenylboronic acid</strong> (101 mg, 1.01 mmol), LiCl (84 mg, 2.02 mmol), (PPh3)2PdCl2 (24 mg, 0.03 mmol), 1.0 M aqueous Na2CO3 (1.68 mL, 1.68 mmol), in toluene (8 mL)-EtOH (8 mL) was stirred in an oil bath (105 C.) for 96 h. The reaction mixture was then cooled to r.t., diluted with AcOEt and saturated brine and partitioned. The aqueous layer was extracted with AcOEt (2*). The combined organic solutions were dried (MgSO4) and concentrated. The residual oil was purified by means of PTLC plates using AcOEt:hexane=1:1 (v/v) as eluent to afford the olefin 61 (118 mg, 45%) as an oil; 1H NMR (400 MHz; CDCl3) delta 1.88 (d, J=1.0 Hz, 3H), 1.94 (d, J=1.0 Hz, 3H), 3.96 (s, 3H), 6.37 (s, 1H), 7.39-7.46 (m, 3H), 7.49-7.54 (m, 1H), 7.59 (s, 1H), 7.63-7.68 (m, 2H), 7.75 (s, 1H), 7.90 (d, J=1.8 Hz, 1H), 8.23 (d, J=1.8 Hz, 1H).

Reference： [1]Patent: EP1749829,2007,A1 .Location in patent: Page/Page column 64
[2]Patent: US2007/72896,2007,A1 .Location in patent: Page/Page column 62

15
[ 923584-14-9 ]
[ 14559-88-7 ]
[ 923584-06-9 ]

Yield	Reaction Conditions	Operation in experiment
66%	With sodium carbonate; lithium chloride;bis-triphenylphosphine-palladium(II) chloride; In ethanol; water; toluene; for 3h;Heating / reflux;	1-Benzenesulfonyl-5-(2-methyl-propenyl)-3-[1-(2-morpholin-4-yl-ethyl)-1H-pyrazol-4-yl]-1H-pyrrolo[2,3-b]pyridine (93) Bromide 92 (158 mg, 0.31 mmol; prepared in analogous way to 20), isobutenyl boronic acid (40 mg, 0.40 mmol) and (PPh3)2PdCl2 (30 mg, 43 mumol) in toluene:EtOH 1:1 (2 mL) was added LiCl (50 mg, 1.18 mmol) and 1.0 M aq. Na2CO3 solution (0.5 mL). The mixture was refluxed (bath temperature 115C) for 3 h. Saturated aqueous NaHCO3 (50 mL) was added, and the mixture was extracted with AcOEt (2 x 75 mL). The combined organic solutions were dried (MgSO4) and concentrated to afford a brown solid (175 mg). The crude product was purified by SGC using MeOH:CH2Cl2:AcOEt=2:49:49 (v/v) as eluent to afford 93 as an off-white powder (99 mg, 0.20 mmol, 66%). 1H NMR (400 MHz, CDCl3) delta 1.87 (s, 3H), 1.96 (s, 3H), 2.53 (t, J = 4.6 Hz, 4H), 2.88 (t, J = 6.6 Hz, 2H), 3.73 (t, J = 4.6 Hz, 4H), 4.33 (t, J = 6.6 Hz, 2H), 6.32 (1H, s, 1H), 7.51 (t, J = 7.8 Hz, 2H), 7.60 (t, J = 7.5 Hz, 1H), 7.77 (s, 2H), 7.78 (s, 1H), 7.80 (d, J = 1.9 Hz, 1H), 8.23 (d, J = 7.6 Hz, 2H), 8.37 (d, J = 1.9 Hz, 1H).
66%	With sodium carbonate; lithium chloride;bis-triphenylphosphine-palladium(II) chloride; In ethanol; water; toluene; at 115℃; for 3h;	1-Benzenesulfonyl-5-(2-methyl-propenyl)-3-[1-(2-morpholin-4-yl-ethyl)-1H-pyrazol-4-yl]-1H-pyrrolo[2,3-b]pyridine (93) Bromide 92 (158 mg, 0.31 mmol; prepared in analogous way to 20), isobutenyl boronic acid (40 mg, 0.40 mmol) and (PPh3)2PdCl2 (30 mg, 43 mumol) in toluene:EtOH 1:1 (2 mL) was added LiCl (50 mg, 1.18 mmol) and 1.0 M aq. Na2CO3 solution (0.5 mL). The mixture was refluxed (bath temperature 115 C.) for 3 h. Saturated aqueous NaHCO3 (50 mL) was added, and the mixture was extracted with AcOEt (2*75 mL). The combined organic solutions were dried (MgSO4) and concentrated to afford a brown solid (175 mg). The crude product was purified by SGC using MeOH:CH2Cl2:AcOEt=2:49:49 (v/v) as eluent to afford 93 as an off-white powder (99 mg, 0.20 mmol, 66%). 1H NMR (400 MHz, CDCl3) delta 1.87 (s, 3H), 1.96 (s, 3H), 2.53 (t, J=4.6 Hz, 4H), 2.88 (t, J=6.6 Hz, 2H), 3.73 (t, J=4.6 Hz, 4H), 4.33 (t, J=6.6 Hz, 2H), 6.32 (1H, s, 1H), 7.51 (t, J=7.8 Hz, 2H), 7.60 (t, J=7.5 Hz, 1H), 7.77 (s, 2H), 7.78 (s, 1H), 7.80 (d, J=1.9 Hz, 1H), 8.23 (d, J=7.6 Hz, 2H), 8.37 (d, J=1.9 Hz, 1H).

Reference： [1]Patent: EP1749829,2007,A1 .Location in patent: Page/Page column 80
[2]Patent: US2007/72896,2007,A1 .Location in patent: Page/Page column 76-77

16
[ 938181-60-3 ]
[ 14559-88-7 ]
[ 1215228-24-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; ethanol; water; at 150℃; for 0.277778h;Microwave;	To a solution of 5-bromo-6-[(methyloxy)methyl]-3-(2-phenylethyl)-2-{2- [(phenylmethyl)oxy]phenyl}-4(3H)-pyrimidinone (0.50 g, 0.99 mmol) in dioxane was added 2,2- dimethylenylboronic acid (0.20 g, 1.98 mmol) dissolved in solvent mixture of 0.5 mL ethanol and 0.5 mL of dioxane, and 0.5 mL of aqueous sodium carbonate (0,09 g, 0.8 mmoles) ina~ rnicowave reaction vessel. To this was added Pd(PPh3J4 (0.172 g, 0.15 mmol) and irradiated to 15O0C for 1000 seconds. The reaction mixture was filtered through syringe filter (Acrodisc CR25mm with 0.2 deltam PTFE membrane). The filtrate was diluted with EtOAc and washed with brine, separated, dried over sodium sulfate, filtered, concentrated in vacuo and the residue was purified by chromatography on silica gel (Biotage) to afford the desired product.

Reference： [1]Patent: WO2007/62370,2007,A2 .Location in patent: Page/Page column 72

17
[ 938180-93-9 ]
[ 14559-88-7 ]
[ 938180-94-0 ]

Yield	Reaction Conditions	Operation in experiment
40%	With sodium carbonate; In 1,4-dioxane; ethanol; water; at 150℃; for 0.277778h;Microwave;	To a solution of 5-bromo-6-[2-(methyloxy)ethyl]-3-(2-phenylethyl)-2-{2- [(phenylmethyl)oxy]phenyJ}-4(3H)-pyrirnidinone (0.2 g, 0.39 mmoles) in dioxane (5 ml_) was added 2-methyl-1-propen-1-yl-boronic acid (0.077 g) dissolved in solvent mixture of 0.5 mL ethanol and 0.5 mL of aqueous sodium carbonate (0.19 g, 0.39 mmoles) in a microwave reaction vessel. This mixture was irradiated to 15O0C for 1000 seconds. The reaction mixture was filtered through syringe filter (Acrodisc CR25mm with 0.2 Dm PTFE membrane). The filtrate was diluted with EtOAc and washed with brine and the organic layer was separated, dried over sodium sulfate, filtered and concentrated. The residue was purified by chromatography on silica gel (30% ethyl acetate/ hexane) to afford the desired product (0.20 g) in 40% yield. Catalytic hydrogenolysis provided the title compound: MS(ES) m/e 405[M+H\|+.

Reference： [1]Patent: WO2007/62370,2007,A2 .Location in patent: Page/Page column 130

18
[ 14559-88-7 ]
[ 1010113-27-5 ]

Reference： [1]Advanced Synthesis and Catalysis,2018,vol. 360,p. 4241 - 4245
[2]Journal of Organic Chemistry,1953,vol. 18,p. 895
[3]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: B: B-Verb.13, 4.7.2.2, page 189 - 196

19
[ 14559-88-7 ]
[ 1092446-64-4 ]
[ 1092447-88-5 ]

Yield	Reaction Conditions	Operation in experiment
73%	With potassium carbonate;palladium anchored homogeneous catalyst, FibreCatPd(0) (4.84percentPd); In 1,4-dioxane; ethanol; water; at 120℃; for 7h;Microwave irradiation;	EXAMPLE 148; 5-Fluoro-2- [3-methyl-2-( 2-methyl-pr openyD-benzoylaminol -indan-2-carboxylic acid ethyl ester (148):To a solution of 5-fluoro-2-(2-iodo-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester (400mg, 0.85mmol) and 2,2-dimethyethylenelboronic acid (342mg, 3.42mmol) in EtOH132 <n="134"/>(1OmL) and dioxane (5mL) is added palladium anchored homogeneous catalyst, FibreCatPd(O) (4.84% Pd, 186mg, 8.5%mmol) and 2M aqueous solution OfK2SO4 (1.7ImL, 3.42mmol). The resulting reaction mixture is covered with argon and run in a microwave reaction: 1200C, 7h. After concentration in vacuo, the residue is purified by HPLC to give a pure product (148) as a colorless oil (245mg, 73%).1H NMR (CDCl3, 300MHz): delta 1.26(t, 3H), 1.34(d, 3H), 1.71(dd, 3H), 2.15(s, 3H), 3.25(br dd, 2H), 3.65(br dd, 2H), 4.24(q, 2H), 6.12(s, IH), 6.86-6.92(m, 2H), 7.19-7.26(m, 4H), 7.65(d, IH) LC/MS (ES+) m/z = 396.18

Reference： [1]Patent: WO2008/151211,2008,A1 .Location in patent: Page/Page column 132-133

20
[ 14559-88-7 ]
[ 1092447-91-0 ]
[ 1092445-74-3 ]
[ 1092447-92-1 ]

Yield	Reaction Conditions	Operation in experiment
38%; 29%	With water; potassium carbonate;palladium anchored homogeneous catalyst, FibreCatPd(0) (4.84percentPd); In 1,4-dioxane; ethanol; at 120℃; for 6h;Microwave irradiation;	EXAMPLES 157 and 158; 5-,6-Difluoro-2- [3-methyl-2-( 2-methyl-propenyl)-benzoylaminol -indan-2-carboxylic acid ethyl ester (157) and 5,6-Difluoro-2-r3-methyl-2-(2-methyl-propenyl)-benzoylaminol- indan-2-carboxylic acid (158): To a solution of 5,6-difluoro-2-(2-iodo-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester (400mg, 0.82mmol) and 2,2-dimethyethylenelboronic acid (328mg, 3.28mmol) in EtOH (1OmL) and dioxane (5mL) is added palladium anchored homogeneous catalyst, FibreCatPd(O) (4.84% Pd, 180mg, 8.2%mmol) and 2M aqueous solution OfK2SO4 (1.64mL, 3.28mmol). The resulting reaction mixture is covered with argon and run in a microwave reaction: 1200C, 6h. After concentration in vacuo, the residue is purified by HPLC to give two137 <n="139"/>pure products: (157) as white solid (lOOmg, 29%) and (158) as white solid as well (120mg,38%).(157): 1H NMR (CDCl3, 300MHz): delta 1.26(t, 3H), 1.38(d, 3H), 1.76(s, 3H), 2.15(s, 3H), 3.27(d, 2H), 3.59(d, 2H), 4.24(q, 2H), 6.14(s, IH), 6.98-7.31(m, 5H), 7.61(d, IH) LC/MS (ES+) m/z = 414.20(158): 1H NMR (CDCl3, 300MHz): delta 1.34(d, 3H), 1.79(s, 3H), 2.15(s, 3H), 3.26(d, 2H), 3.75(d, 2H), 6.09(s, IH), 7.02(t, 2H), 7.21-7.34(m, 3H), 7.77(d, IH) LC/MS (ES+) m/z = 386.19

Reference： [1]Patent: WO2008/151211,2008,A1 .Location in patent: Page/Page column 137-138

21
[ 14559-88-7 ]
[ 1092447-82-9 ]
[ 1092447-84-1 ]

Yield	Reaction Conditions	Operation in experiment
78%	With caesium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; at 110℃; for 2h;Microwave irradiation;	EXAMPLE 134; 2-r3-Methyl-2-(7-methyl-propenyl)-benzoylaminol-indan-2-carboxylic acid ethyl esterTo a solution of 2-(2-iodo-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester (400mg, 0.89mmol) and 2,2-dimethyethylenelboronic acid (133mg, 1.34mmol) in dioxane (15mL) is added PdCl2(dppf) ([l,r-bis(diphenylphosphine)ferrocene]-dichloropalladium(II), 73mg, 8.9%mmol) and 2M aqueous solution Of CsCO3 (1.34mL, 2.67mmol). The resulting reaction mixture is covered with argon and run in a microwave reaction: 1100C, 2h. After concentration in vacuo, the residue is purified by flash column chromatography (12Og silica gel, gradient elution: 5-50% EtOAc in heptane) to give a pure product (134) as a pale yellow solid (523mg, 78%).1H NMR (CDCl3, 300MHz): delta 1.27(t, 3H), 1.30(s, 3H), 1.65(s, 3H), 2.14(s, 3H), 3.24(br d, 2H), 3.70(br d, 2H), 4.25(q, 2H), 6.10(s, IH), 7.02(s, IH), 7.17-7.26(m, 6H), 7.69(d, IH) LC/MS (ES+) m/z = 378.22

Reference： [1]Patent: WO2008/151211,2008,A1 .Location in patent: Page/Page column 125

22
[ 14559-88-7 ]
[ 1092448-25-3 ]
[ 1092448-26-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;palladium anchored homogeneous catalyst, FibreCatPd(0) (4.84percentPd); In ethanol; water; at 110℃; for 5h;Microwave irradiation;	EXAMPLE 224; 2- [6- Amino-3-methyl-2-( 2-methyl-pr openyD-benzoylaminol -indan-2-carboxylic acid ethyl ester (224) To a solution of (223) (278mg, 0.67mmol) and 2,2-dimethylethyleneboronic acid (134mg,1.34mmol) in 10ml EtOH is added palladium anchored homogeneous catalyst, FibreCatPd(O), (4.84%Pd, 195mg, 0.089mmol) and 2M aqueous solution OfK2SO4 (1.78mL, 3.56mmol). The resulting reaction mixture is covered with argon and run in a microwave reaction: 1100C, 5h. After concentration in vacuo, the residue is purified by HPLC to give 380mg brown semi- solid (224).

Reference： [1]Patent: WO2008/151211,2008,A1 .Location in patent: Page/Page column 184-185

23
[ 14559-88-7 ]
[ 1092449-74-5 ]
[ 1092449-75-6 ]

Yield	Reaction Conditions	Operation in experiment
92%	With sodium hydrogencarbonate;tetrakis(triphenylphosphine) palladium(0); In water; N,N-dimethyl-formamide; at 110℃; for 5h;	Example 294; 2-r2-methyl-3-(^-methyl-l-propenyl)benzoylaminolindan-2-carboxylic acid ethyl ester (294)A suspension of 2-(3-bromo-2-methylbenzoylamino)indan-2-carboxylic acid ethyl ester (293) (402mg-lmmol) and 2-methyl-l-propenylboronic acid (200mg, 2mmol, 2eq) in dry DMF (2OmL) and saturated NaHCObeta (5mL) is degassed for lOmin and then treated with tetrakis(triphenylphosphine)palladium(0) (400mg). The mixture is stirred at 1100C for 5h. The reaction is cooled and the DMF removed in vacuo and the residue diluted with water (8OmL). The aqueous is filtered through celite and extracted with EtOAc (3 x 5OmL). The organic extracts are washed with water (2 x 3OmL) and brine (2 x 3OmL), and dried over MgSO4. The organic phase is then concentrated in vacuo and purified by flash chromatography (12Og silica gel, 30% EtOAc in heptane) to give pale yellow oil (350mg, 92%).LC/MS (E/S+) m/z 378

Reference： [1]Patent: WO2008/151211,2008,A1 .Location in patent: Page/Page column 224-295

24
[ 14559-88-7 ]
[ 1124382-78-0 ]
N-[5-(2-methylprop-1-en-1-yl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide dihydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%		Example 94 : N-[5-(2-methylprop-l-en-l-yl)[l.,2,41triazolo[l,5-alpyridin-2- yll nicotinamide dihydrochloride; <n="112"/>(94)N-(5-chloro[l,2,4]triazolo[l,5-a]pyridin-2-yl)nicotinamide ((B4), 141.00 mg; 0.52 mmol; 1.00 eq.), <strong>[14559-88-7]2,2-dimethylethenylboronic acid</strong> (Synthonix, 102.96 mg; 1.03 mmol; 2.00 eq.), cesium fluoride (156.53 mg; 1.03 mmol; 2.00 eq.) and bis(triphenylphosphine)palladium(II) chloride (36.16 mg; 0.05 mmol; 0.10 eq.) were flushed with nitrogen in a sealed vial. THF (degassed with nitrogen, 1.50 mL) and water (1 mL) were then added and the mixture was heated at 1200C O/N in an oil bath. A solution of saturated NH4Cl was added and the reaction mixture was extracted with EtOAc (twice). Combined Organic phases were washed with brine, dried over magnesium sulfate, filtered and concentrated to give 186 mg of a yellow foam. Hydrochloride salt was then obtained by addition of Et2OZHCl (1 M solution) to a solution of this crude in DCM. The precipitate obtained was filtered and dried under vacuum at 400C to give the title compound as a beige solid (181 mg, 96%). HPLC, Rt: 2.05 min. (purity 92.3%). LC/MS, M+(ESI): 293.9, M (ESI): 291.9.

Reference： [1]Patent: WO2009/27283,2009,A1 .Location in patent: Page/Page column 110-111

25
C₁₀H₂₁BO₂ [ No CAS ]
[ 14559-88-7 ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 3850 - 3851

26
[ 14559-88-7 ]
potassium 2,2-dimethylethenyltrifluoroborate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 3850 - 3851
[2]Organic Letters,2010,vol. 12,p. 2004 - 2007

27
[ 14559-88-7 ]
[ 123043-88-9 ]
[ 1160739-89-8 ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 5118 - 5121

28
[ 14559-88-7 ]
[ 134074-41-2 ]
[ 1160739-92-3 ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 5118 - 5121

29
[ 14559-88-7 ]
[ 329689-23-8 ]
[ 1160739-96-7 ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 5118 - 5121

30
[ 14559-88-7 ]
[ 1142224-41-6 ]
[ 1142225-87-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate;palladium diacetate; In water; N,N-dimethyl-formamide; at 70℃; for 23h;Inert atmosphere;	Methyl 3-(2-methyl-1-propenyl)-4-(tetrahydro-2H-pyran-2- yloxy)benzoate (T23.1). A mixture of methyl 3-bromo-4-(tetrahydro-2H-pyran-2- yloxy)benzoate T3.2 (0.500 g, 1.6 mmol), palladium acetate (0.036 g, 0.16 mmol), S- Phos (0.13 g, 0.32 mmol) and tripotassium phosphate (0.32 niL, 4.0 mmol) in DMF (10.00 mL, 129 mmol) and water (0.40 mL, 22 mmol) was stirred. The mixture was purged with nitrogen and placed under vacuum and the process repeated three times. Before heating, 2-methylprop- 1 -enylboronic acid (0.24 g, 2.4 mmol, commercially available from Synthonix, Cat. No. D3007G1) was added, and the mixture was heated to 70C and stirred for 23 hours. The mixture was then cooled to room temperature, diluted with brine, and extracted three times with EtOAc. After drying over anhydrous magnesium sulfate and filtering, the organic solvent was removed under reduced pressure and the product was then purified on silica gel (0-10% EtOAc in hexanes) to yield T23.1 as a colorless oil (0.460 g, 100% yield).
100%	With potassium phosphate;2-dicyclohexylphosphino-2?,6?-dimethoxybiphenyl; palladium diacetate; In water; N,N-dimethyl-formamide; at 70℃; for 23h;Inert atmosphere;	Methyl 3-(2-methyl-1-propenyl)-4-(tetrahydro-2H-pyran-2- yloxy)benzoate (T13.1). A mixture of methyl 3-bromo-4-(tetrahydro-2H-pyran-2- yloxy)benzoate T6.6 (0.500 g, 1.6 mmol), palladium acetate (0.036 g, 0.16 mmol), S- Phos (0.13 g, 0.32 mmol) and tripotassium phosphate (0.32 mL, 4.0 mmol) in DMF (10.00 mL, 129 mmol) and water (0.40 mL, 22 mmol) was stirred. The mixture was purged with nitrogen and placed under vacuum and the process repeated three times. Before heating, 2-methylprop-1-enylboronic acid (0.24 g, 2.4 mmol, commercially available from Synthonix, Cat. No. D3007G1) was added, and the mixture was heated to 70C and stirred for 23 hours. The mixture was then cooled to room temperature, diluted with brine, and extracted three times with EtOAc. After drying over anhydrous magnesium sulfate and filtering, the organic solvent was removed under reduced pressure and the product was then purified on silica gel (0-10% EtOAc in hexanes) to yield T13.1 as a colorless oil (0.460 g, 100% yield).

Reference： [1]Patent: WO2010/45258,2010,A2 .Location in patent: Page/Page column 200
[2]Patent: WO2009/111056,2009,A1 .Location in patent: Page/Page column 179-180

31
[ 14559-88-7 ]
[ 1055880-27-7 ]
[ 1055880-88-0 ]

Yield	Reaction Conditions	Operation in experiment
89.1%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 85℃; for 12h;Inert atmosphere; Saturated solution;	Example 51; 9-(2-methylpropyl)-2,3,4,5-tetrahydro-1,4-benzoxazepine hydrochloride; (1) tert-butyl 9-(2-methylpropa-1-ene-1-yl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate; A mixture of tert-butyl 9-bromo-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (328 mg, 1.00 mmol), <strong>[14559-88-7]2,2-dimethylethenylboronic acid</strong> (98.0 mg, 1.00 mmol), saturated aqueous sodium carbonate solution (14 ml) and tetrakis(triphenylphosphine)palladium(0) (32.6 mg, 0.0282 mmol) in dimethoxyethane (10 ml) was stirred at 85C for 12 hr under a nitrogen atmosphere. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to give the desired product (270 mg, 89.1%) as an oil. 1H-NMR (CDCl3) delta; 1.42 (9H, s), 1.79 (3H, s), 1.92 (3H, s), 3.77-3.80 (2H, m), 4.00-4.03 (2H, m), 4.40-4.46 (2H, m), 6.29 (1H, s), 6.93-7.14 (3H, m).

Reference： [1]Patent: EP2123644,2009,A1 .Location in patent: Page/Page column 70

32
[ 38614-36-7 ]
[ 14559-88-7 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 6104 - 6107
[2]Organic Letters,2011,vol. 13,p. 4958 - 4961
[3]Organic Letters,2010,vol. 12,p. 2004 - 2007
[4]Journal of the American Chemical Society,2011,vol. 133,p. 13774 - 13777

33
[ 14559-88-7 ]
[ 1228504-07-1 ]
[ 1228504-08-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; ethanol; water; at 150℃; for 0.0833333h;Microwave irradiation;	Example 4 Preparation of [5-(2-Methyl-propenyl)-7-p-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(4-methyl-pyrazin-2-ylmethyl)-amine The mixture of (5-bromo-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-(5-methyl-pyrazin-2-ylmethyl)-amine (0.36 g, 1.00 mmol), <strong>[14559-88-7]2,2-dimethylethenylboronic acid</strong> (0.13 g, 1.2 mmol), Pd(PPh3)4 (60 mg g, 0.05 mmol), Na2CO3 (2N, 2 mL, 4 mmol) in ethanol-H2O-DME (3 mL-4 mL-12 mL) was heated to 150 C. for 5 min in microwave reactor. After filtration, the solvent was removed and the residue obtained was purified by silica gel chromatography to afford 0.29 g of [5-(2-methyl-propenyl)-7-p-tolyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-(5-methyl-pyrazin-2-ylmethyl)-amine. MS (ESI) 385.6 (M+H)+

Reference： [1]Patent: US2010/144758,2010,A1 .Location in patent: Page/Page column 61; 63

34
[ 90011-02-2 ]
[ 14559-88-7 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 3147 - 3150

35
[ 14559-88-7 ]
[ 4408-64-4 ]
[ 1104637-50-4 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 3147 - 3150

36
[ 14559-88-7 ]
[ 1330780-51-2 ]
(CH₃)2CCHB(OCOCH₂)2NC₇H₈(CH₃)3 [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2011,vol. 133,p. 13774 - 13777

37
[ 14559-88-7 ]
[ 1330579-56-0 ]
[ 1330579-19-5 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 4958 - 4961

38
[ 31951-75-4 ]
[ 14559-88-7 ]
[ 1330579-20-8 ]
4-(1H-indol-3-yl)-6-methylhept-5-en-2-one [ No CAS ]

Reference： [1]Organic Letters,2011,vol. 13,p. 4958 - 4961

39
[ 14559-88-7 ]
[ 1336967-02-2 ]
[ 1336967-04-4 ]