[ CAS No. 352530-22-4 ] {[proInfo.proName]}

Name: 352530-22-4|4-Fluoro-3-nitrophenylboronic acid|95%
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SKU: A108032
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Quality Control of [ 352530-22-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 352530-22-4 ]

SDS Specification

Alternatived Products of [ 352530-22-4 ]

Product Details of [ 352530-22-4 ]

CAS No. :	352530-22-4	MDL No. :	MFCD08277236
Formula :	C₆H₅BFNO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JDPKQZFQCPEJNH-UHFFFAOYSA-N
M.W :	184.92	Pubchem ID :	24901765
Synonyms :

Calculated chemistry of [ 352530-22-4 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	5.0
Num. H-bond donors :	2.0
Molar Refractivity :	45.05
TPSA :	86.28 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) :	-6.89 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	0.76
Log Po/w (WLOGP) :	-0.17
Log Po/w (MLOGP) :	-0.39
Log Po/w (SILICOS-IT) :	-2.38
Consensus Log Po/w :	-0.44

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.67
Solubility :	3.91 mg/ml ; 0.0211 mol/l
Class :	Very soluble
Log S (Ali) :	-2.15
Solubility :	1.3 mg/ml ; 0.00705 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-0.95
Solubility :	20.8 mg/ml ; 0.112 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	3.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.25

Safety of [ 352530-22-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 352530-22-4 ]

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

Upstream synthesis route of [ 352530-22-4 ]
Downstream synthetic route of [ 352530-22-4 ]

[ 352530-22-4 ] Synthesis Path-Upstream 1~3

1
[ 352530-22-4 ]
[ 873566-75-7 ]

Yield	Reaction Conditions	Operation in experiment
80.7%	With palladium on activated charcoal; hydrogen In methanol at 55℃; Sealed tube	Hydrogenation of 3-nitro-4-fluorobenzeneboronic acid (63 g) was placed in a 500 mL single-necked flask. Methanol (100 mL) and palladium carbon (6.3 g, 10percent) were added and sealed with a stopper. Water chestnut vacuum, needle into the hydrogen. The reaction flask was placed in an oil bath at 55 ° C and the reaction was stirred. Hydrogen balloon reaction after the replacement until no longer absorb hydrogen. The reaction solution was filtered through a Buchner funnel to remove palladium-carbon, dried to dryness, beaten with n-heptane, and dried in vacuo. The solid was dissolved in methanol (30 mL), 150 mL of water was added, a large amount of solid was precipitated, the methanol was distilled off and a portion of water was distilled off and the temperature was lowered to 5 ° C. The Buchner funnel was filtered off as a pale gray solid and dried in vacuo to give The final product was 42.6 g, the yield was 80.7percent, the structure was confirmed by 1Hz NMR, and the HPLC was 99.1percent.

Reference： [1] Patent: CN103626791, 2016, B, . Location in patent: Paragraph 0024; 0025; 0030

2
[ 1765-93-1 ]
[ 352530-22-4 ]

Yield	Reaction Conditions	Operation in experiment
31.5%	With nitric acid In ethanol at -45 - -35℃;	fuming nitric acid (140 mL) was placed in a 250 mL four-necked flask and stirred at -35 ° C to -45 ° C with a dry ethanol bath. Fluorobenzene boric acid (20 g) was thoroughly dried and pulverized in batches and slowly added to a four-necked flask to maintain the reaction temperature between -35 ° C and -45 ° C. After the addition of p-fluorobenzene boronic acid, the reaction was complete by TLC. The reaction solution into 200g crushed ice, rapid and stirring, a yellow solid precipitation, Buchner funnel filter, ice water 20mL washing 2 times, drained. The resulting filtrate was adjusted to pH 6 with sodium bicarbonate and extracted with ethyl acetate. The oil phase was combined, dried over magnesium sulfate, dried to dryness, n-heptane beating, To give a pale yellow solid, 8.3 g, yield 31.5percent

Reference： [1] Patent: CN103626791, 2016, B, . Location in patent: Paragraph 0024; 0029

3
[ 460-00-4 ]
[ 352530-22-4 ]

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

[ 352530-22-4 ] Synthesis Path-Downstream 1~60

1
[ 352530-22-4 ]
[ 1020174-07-5 ]
[ 1020173-81-2 ]

Yield	Reaction Conditions	Operation in experiment
44%		Example B27 <strong>[352530-22-4]4-Fluoro-3-nitrophenylboronic acid</strong> (0.9 g, 4.9 mmol) was dissolved in CH2Cl2 (10 mL) and pyridine (1 mL) with MS (activated 4A) and dried for 6 hours. A mixture of <strong>[352530-22-4]4-fluoro-3-nitrophenylboronic acid</strong>, tert-butyl 3-isopropyl-1H-pyrazole-5-carboxylate (1.0 g, 4.9 mmol), copper(II) acetate (0.88 g, 4.9 mmol) and molecular sieves (4A activated, powder) was stirred at RT for 7 days open to the air. The reaction mixture was filtered through a pad of Celite. The filtrate was concentrated in vacuo and purified by silica gel column chromatography (EtOAc/hexane) to obtain tert-butyl 1-(4-fluoro-3-nitrophenyl)-3-isopropyl-1H-pyrazole-5-carboxylate (0.74 g, 44% yield). MS (ESI) m/z: 350.3 (M+H+).
44%	With pyridine; copper diacetate; In dichloromethane; at 20℃; for 168h;Molecular sieve;	<strong>[352530-22-4]4-Fluoro-3-nitrophenylboronic acid</strong> (0.9 g, 4.9 mmol) was dissolved in CH2CI2 (10 mL) and pyridine (1 mL) with MS (activated 4A) and dried for 6 hours. A mixture of <strong>[352530-22-4]4-fluoro-3-nitrophenylboronic acid</strong>, tert-butyl 3-isopropyl-lH- pyrazole-5-carboxylate (1.0 g, 4.9 mmol), copper(II) acetate (0.88 g, 4.9 mmol) and molecular sieves (4A activated, powder) was stirred at RT for 7 days open to the air. The reaction mixture was filtered through a pad of Celite. The filtrate was concentrated in vacuo and purified by silica gel column chromatography (EtOAc/hexane) to obtain tert- butyl l-(4-fluoro-3-nitrophenyl)-3-isopropyl-lH-pyrazole-5-carboxylate (0.74 g, 44% yield). MS (ESI) m/z: 350.3 (M+H+).

Reference： [1]Patent: US2008/90856,2008,A1 .Location in patent: Page/Page column 47
[2]Patent: WO2013/36232,2013,A2 .Location in patent: Paragraph 00344

2
[ 352530-22-4 ]
[ 106-40-1 ]
[ 1414931-66-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; at 85℃; for 3h;	STEP A: 2',4'-dichloro-[1,1'-biphenyl]-4-amine 4-Bromoaniline (500 mg, 2.9 mmol), <strong>[352530-22-4](4-fluoro-3-nitrophenyl)boronic acid</strong> (720 mg, 3.8 mmol), Pd(dppf)Cl2 (721 mg, 0.9 mmol), and K2CO3 (2.4 g, 17.4 mmol) were dissolved in 1,4-dioxane (10 mL) and water (4 mL) and the resulting mixture was heated to 85 C. After 3 h the resulting mixture was cooled to room temperature and filtered. The filtrate was diluted with EtOAc, washed with water, dried (Na2SO4), concentrated and purified via column chromatography to yield the title compound.

Reference： [1]Patent: US2012/302641,2012,A1 .Location in patent: Page/Page column 26

3
[ 352530-22-4 ]
[ 1423134-92-2 ]
[ 1423135-10-7 ]

Yield	Reaction Conditions	Operation in experiment
40%	With potassium fluoride; tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 60 - 100℃; for 29h;	To 300.0 mg (0.49 mmol) tert-butyl 4-{3-[(3R)-3-[1-(5-bromopyridin-3-yl)-3-methoxy-3- oxopropyl]carbamoyl}piperidin-1-yl]-3-oxopropyl}piperidine-1-carboxylate (example 8c) in 12 ml toluene were added 11.4 mg (0.01 mmol) tetrakis(triphenylphosphine)palladium(0), 109.2 mg (0.59 mmol) <strong>[352530-22-4](4-fluoro-3-nitro-phenyl)boronic acid</strong> in 3.0 ml ethanol and 88.7 mg (1.53 mmol) potassium fluoride in 3.0 ml water. The mixture was stirred at 100 C for 9 hours and at 60 C for 20 hours, diluted with water and extracted with ethyl acetate. The organic phase was dried over sodium sulfate and concentrated in vacuum. Chromatography over 10 g silica gel (dichloromethane/ethanol 100/0-95/5-90/ 0) gave 147 mg (40 %) (erf-butyl 4-{3-[(3R)-3-({1-[5-(4-fluoro-3-nitrophenyl)pyridin-3-yl]-3-methoxy-3-oxopropyl}carbamoyl)piperidin-1-yl]- 3-oxopropyl}piperidine-1-carboxylate. UPLC (ACN-HCOOH): Rt. = 1.23 min MS (ES * ): m/e = 670.3 (M + H*) MS (ES ): m/e = 668.5 (M - H), 714.6 (M + HCOO )

Reference： [1]Patent: WO2013/23795,2013,A1 .Location in patent: Page/Page column 149; 150

4
[ 352530-22-4 ]
[ 1020174-07-5 ]
[ 1020173-82-3 ]

Reference： [1]Patent: WO2013/36232,2013,A2

5
[ 352530-22-4 ]
[ 1603845-21-1 ]
[ 1603845-23-3 ]

Yield	Reaction Conditions	Operation in experiment
85%	With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In 1,4-dioxane; water; at 80℃; for 2h;	To a solution of tert-butyl 4-(4-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)cyclohexyl)piperazine-1-carboxylate (360 mg, 0.68mmol) in dioxane (6 mL) were added <strong>[352530-22-4](4-fluoro-3-nitrophenyl)boronic acid</strong> (177 mg, 0.96mmol) and 1M aqueous solution of sodium carbonate (2 mL) at ambient temperature. The resulting suspension was degassed with argon for 3 min and bis(triphenylphosphine)palladium(II) dichloride (35 mg, 0.05 mmol) was added. The mixturewas heated to 80 C and stirred for 2 hr. It was diluted with dichloromethane (30 mL), washed with water (30 mL) and concentrated in vacuo. The residue was purified by flash column chromatography (10% methanol-dichloromethane) to provide tert-butyl 4-(4-(4-amino-3-(4-fluoro-3-nitrophenyl)-1H-pyrazolo[3,4-d]pyrimidin-lyl)cyclohexyl)piperazine- 1-carboxylate (312 mg, 85 %). MS m/z: 541.75 (M+l).

Reference： [1]Patent: WO2014/63061,2014,A1 .Location in patent: Paragraph 00341

6
[ 352530-22-4 ]
[ 1603845-26-6 ]

Reference： [1]Patent: WO2014/63061,2014,A1

7
[ 352530-22-4 ]
[ 1603845-30-2 ]

Reference： [1]Patent: WO2014/63061,2014,A1

8
[ 352530-22-4 ]
[ 1603845-31-3 ]

Reference： [1]Patent: WO2014/63061,2014,A1

9
[ 352530-22-4 ]
C₃₂H₃₆N₈O₃*C₂HF₃O₂ [ No CAS ]

Reference： [1]Patent: WO2014/63061,2014,A1

10
[ 352530-22-4 ]
C₄₂H₅₂N₈O₇ [ No CAS ]

Reference： [1]Patent: WO2014/63061,2014,A1

11
[ 352530-22-4 ]
1-(4-(4-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)cyclohexyl)piperazin-1-yl)ethan-1-one [ No CAS ]
[ 1603845-25-5 ]

Yield	Reaction Conditions	Operation in experiment
78%	With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In 1,4-dioxane; water; at 80℃; for 2h;	To a solution of tert-butyl 4-(4-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)cyclohexyl)piperazine-1-carboxylate (234 mg, 0.50mmol) in dioxane (6 mL) were added <strong>[352530-22-4](4-fluoro-3-nitrophenyl)boronic acid</strong> (136 mg, 0.74mmol) and 1M aqueous solution of sodium carbonate (2 mL) at ambient temperature. The resulting suspension was degassed with argon for 3 min and bis(triphenylphosphine)palladium(ll) dichloride (47 mg, 0.07 mmol) was added. The mixture was heated to 80 C and stirred for 2 hr. It was diluted with dichloromethane (30 mL),washed with water (30 mL) and concentrated in vacuo. The residue was purified by flash column chromatography (10% methanol-dichloromethane) to 1-(4-(4-(4-amino-3-(4-fluoro-3-nitrophenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)cyclohexyl)piperazin-1-yl)ethanone (188 mg, 78 %). MS m/z: 482.63 (M+l).

Reference： [1]Patent: WO2014/63061,2014,A1 .Location in patent: Paragraph 00343
[2]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 3382 - 3389

12
[ 330793-48-1 ]
[ 352530-22-4 ]
[ 1603845-34-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 3382 - 3389
[2]Patent: WO2014/63061,2014,A1 .Location in patent: Page/Page column 128

13
[ 922500-91-2 ]
[ 352530-22-4 ]
ethyl 2-(3-(4-fluoro-3-nitrophenyl)oxetan-3-yl)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
10.04%	With chloro(1,5-cyclooctadiene)rhodium(I) dimer; potassium hydroxide; In 1,4-dioxane; at 20 - 50℃; for 14h;	To a solution of [Rh(COD)2Cl]2 (26.0 mg, 0.053 mmol) in 1,4-dioxane (5 mL) was added potassium hydroxide (0.915 mL, 1.372 mmol) followed by 2A (150 mg, 1.055 mmol) (rinsed with 1 mL 1,4-dioxane) and a solution of (4-fluoro-3-nitrophenyl)boronic acid (293 mg, 1.583 mmol) in 1,4-dioxane (1.000 mL). After addition of potassium hydroxide, the solution turned into a yellow suspension. After addition of oxetane, it turned into a clear brown solution. After stirring at RT for 12 h, LC-MS showed a new peak. Heated at 50 C for 2 h, no change. After cooling to RT, it was diluted with 5 mL of brine and 10 mL of EtOAc. The aqueous layer was further extracted with EtOAc (3x 10 mL) and the combined organic extracts were washed with water, brine, dried over MgS04, filtered and concentrated. Purification via flash chromatography gave 2B (yellow solid, 30 mg, 0.106 mmol, 10.04 % yield). LC-MS Anal. Calc'd for Ci3H14FN05 283.09, did not show parent ion in MS, Tr = 2.48 min (Method A). XH NMR (400MHz, CHLOROFORM-d) delta 7.90 (dd, J=6.9, 2.5 Hz, 1H), 7.55 (ddd, J=8.6, 4.1, 2.4 Hz, 1H), 7.30 (dd, J=10.3, 8.6 Hz, 1H), 4.96 (d, J=6.4 Hz, 2H), 4.88 (d, J=6.6 Hz, 2H), 4.05 (q, J=7.0 Hz, 2H), 3.18 (s, 2H), 1.18 (t, J=7.2 Hz, 3H)

Reference： [1]Patent: WO2014/150646,2014,A1 .Location in patent: Page/Page column 54; 55

14
[ 717900-67-9 ]
[ 352530-22-4 ]
C₁₇H₁₆FN₅O₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 3382 - 3389

15
[ 352530-22-4 ]
4-[(7-Bromo-2,3-dihydro-1-benzofuran-5-yl)methyl]pyridine [ No CAS ]
4-[7-(4-fluoro-3-nitrophenyl)-2,3-dihydro-1-benzofuran-5-yl]methyl}pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; ethanol; water; at 80℃;Inert atmosphere;	4- [(7-Bromo-2,3 -dihydro- 1 -benzofuran-5 -yl)methyl]pyridine 4 (40 mg, 0.138 mmol, 1 eq.), <strong>[352530-22-4]3-nitro-4-fluorophenylboronic acid</strong> (60 mg, 0.32 mmol, 2.35 eq.), Pd(PPh3)4 (20 mg, 0.017 mmol, 0.12 eq.), and K3P04 (70 mg, 0.33 mmol, 2.4 eq.) were dissolved in DME (2 mL), EtOH (0.5 mL) and water (0.5 mL). The mixture was purged with Ar for 15 minutes and then stirred at 80C overnight. After cooling to rt, the reaction was concentrated, and the residue partitioned between water (10 mL) and DCM (15 mL). The organic layer was separated, dried over Na2SO4, and concentrated. The residue was purified by chromatography (SG, 1-2% MeOH/DCM) to give the title compound as a solid (30 mg, 63% yield). ?H NMR (CDC13, 400 MHz) oe 8.54 (d, J = 5.6Hz, 2H), 8.43 (dd, J = 7.2Hz, 2.4Hz, 1H), 7.98 (m, 1H), 7.33 (dd, J = 8.8Hz, 8.4Hz, 1H), 7.15 (d, J = 5.6Hz, 2H), 7.11 (s, 1H), 7.05 (s, 1H), 4.68 (t, J = 8.4 Hz, 2H), 3.98 (s, 2H), 3.28(t, J = 8.4 Hz, 2H).

Reference： [1]Patent: WO2016/49595,2016,A1 .Location in patent: Paragraph 0275

16
[ 460-00-4 ]
[ 352530-22-4 ]

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

17
[ 1765-93-1 ]
[ 352530-22-4 ]

Yield	Reaction Conditions	Operation in experiment
31.5%	With nitric acid; In ethanol; at -45 - -35℃;	fuming nitric acid (140 mL) was placed in a 250 mL four-necked flask and stirred at -35 C to -45 C with a dry ethanol bath. Fluorobenzene boric acid (20 g) was thoroughly dried and pulverized in batches and slowly added to a four-necked flask to maintain the reaction temperature between -35 C and -45 C. After the addition of p-fluorobenzene boronic acid, the reaction was complete by TLC. The reaction solution into 200g crushed ice, rapid and stirring, a yellow solid precipitation, Buchner funnel filter, ice water 20mL washing 2 times, drained. The resulting filtrate was adjusted to pH 6 with sodium bicarbonate and extracted with ethyl acetate. The oil phase was combined, dried over magnesium sulfate, dried to dryness, n-heptane beating, To give a pale yellow solid, 8.3 g, yield 31.5%

Reference： [1]Patent: CN103626791,2016,B .Location in patent: Paragraph 0024; 0029

18
[ 352530-22-4 ]
[ 873566-75-7 ]

Yield	Reaction Conditions	Operation in experiment
80.7%	With palladium on activated charcoal; hydrogen; In methanol; at 55℃;Sealed tube;	Hydrogenation of 3-nitro-4-fluorobenzeneboronic acid (63 g) was placed in a 500 mL single-necked flask. Methanol (100 mL) and palladium carbon (6.3 g, 10%) were added and sealed with a stopper. Water chestnut vacuum, needle into the hydrogen. The reaction flask was placed in an oil bath at 55 C and the reaction was stirred. Hydrogen balloon reaction after the replacement until no longer absorb hydrogen. The reaction solution was filtered through a Buchner funnel to remove palladium-carbon, dried to dryness, beaten with n-heptane, and dried in vacuo. The solid was dissolved in methanol (30 mL), 150 mL of water was added, a large amount of solid was precipitated, the methanol was distilled off and a portion of water was distilled off and the temperature was lowered to 5 C. The Buchner funnel was filtered off as a pale gray solid and dried in vacuo to give The final product was 42.6 g, the yield was 80.7%, the structure was confirmed by 1Hz NMR, and the HPLC was 99.1%.

Reference： [1]Patent: CN103626791,2016,B .Location in patent: Paragraph 0024; 0025; 0030

19
[ 352530-22-4 ]
(E)-N-(5-(1-methyl-2-oxopiperidin-3-yl)-1-(3-((triisopropylsilyl)oxy)propyl)-1H-benzo[d]imidazol-2(3H)-ylidene)-3-(trifluoromethyl)benzamide [ No CAS ]

Reference： [1]Patent: WO2017/49069,2017,A1

20
[ 352530-22-4 ]
(E)-N-(1-(3-hydroxypropyl)-5-(1-methyl-2-oxopiperidin-3-yl)-1H-benzo[d]imidazol-2(3H)-ylidene)-3-(trifluoromethyl)benzamide [ No CAS ]

Reference： [1]Patent: WO2017/49069,2017,A1

21
[ 352530-22-4 ]
(S,E)-N-(1-(3-hydroxypropyl)-5-(1-methyl-2-oxopiperidin-3-yl)-1H-benzo[d]imidazol-2(3H)-ylidene)-3-(trifluoromethyl)benzamide [ No CAS ]
(R,E)-N-(1-(3-hydroxypropyl)-5-(1-methyl-2-oxopiperidin-3-yl)-1H-benzo[d]imidazol-2(3H)-ylidene)-3-(trifluoromethyl)benzamide [ No CAS ]

Reference： [1]Patent: WO2017/49069,2017,A1

22
[ 352530-22-4 ]
3-(4-fluoro-3-nitro-phenyl)-pyridin-2-ol [ No CAS ]

Reference： [1]Patent: WO2017/49069,2017,A1

23
[ 352530-22-4 ]
3-(4-fluoro-3-nitrophenyl)-1-methylpyridin-2(1H)-one [ No CAS ]

Reference： [1]Patent: WO2017/49069,2017,A1

24
[ 352530-22-4 ]
3-(4-((3-hydroxypropyl)amino)-3-nitrophenyl)-1-methylpyridine-2(1H)-one [ No CAS ]

Reference： [1]Patent: WO2017/49069,2017,A1

25
[ 352530-22-4 ]
1-methyl-3-(3-nitro-4-((3-((triisopropylsilyl)oxy)propyl)amino)phenyl)pyridine-2(1H)-one [ No CAS ]

Reference： [1]Patent: WO2017/49069,2017,A1

26
[ 352530-22-4 ]
3-(3-amino-4-((3-((triisopropylsilyl)oxy)propyl)amino)phenyl)-1-methylpiperidin-2-one [ No CAS ]

Reference： [1]Patent: WO2017/49069,2017,A1

27
[ 352530-22-4 ]
3-(2-amino-1-(3-((triisopropylsilyl)oxy)propyl)-1H-benzo[d]imidazol-5-yl)-1-methylpiperidin-2-one [ No CAS ]

Reference： [1]Patent: WO2017/49069,2017,A1

28
[ 13472-59-8 ]
[ 352530-22-4 ]
3-(4-fluoro-3-nitro-phenyl)-2-methoxypyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium fluoride; palladium diacetate; In tetrahydrofuran; at 70℃; for 16h;Inert atmosphere; Sealed tube;	In a glass reaction vessel equipped with a Teflon-coated screw cap was combined (4-fluoro-3-nitro-phenyl)boronic acid (1.5 eq.), palladium(II) acetate (0.05 eq.), dicyclohexyl-(2'6'-dimethoxy-biphenyl-2-yl)- phosphine (0.1 eq.) and potassium fluoride (3 eq.) in THF (0.11 M). The reaction suspension was then sub-surface purged with nitrogen for 15 min before <strong>[13472-59-8]3-bromo-2-methoxy-pyridine</strong> (1 eq.) was added. The reaction vessel was then tightly sealed and heated at 70C for 16 h. The resulting brown reaction suspension was diluted with iBuOMe and washed sequentially with 10% aq. NaHC03, water and brine. The organic extract was then dried over MgS04, filtered and the filtrate concentrated in vacuo to furnish a dark brown solid. Purification of the crude product thus obtained by way of column chromatography (S1O2, gradient elution, Hex -> 3:7 (v/v) Hex: EtOAc) furnished the desired product as a white solid (98% yield).

Reference： [1]Patent: WO2017/49069,2017,A1 .Location in patent: Paragraph 00182

29
[ 352530-22-4 ]
[ 2927-71-1 ]
2-chloro-5-fluoro-4-(4-fluoro-3-nitrophenyl)pyrimidine [ No CAS ]