900174-60-9|(5-Ethoxy-2-fluorophenyl)boronic acid| Ambeed

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Quality Control of [ 900174-60-9 ] Purity: 98% SDS Specification

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Product Details of [ 900174-60-9 ]

CAS No. :	900174-60-9
Formula :	C₈H₁₀BFO₃
M.W :	183.97
SMILES Code :	CCOC1=CC(B(O)O)=C(F)C=C1
MDL No. :	MFCD05664321
InChI Key :	ISJGNUFTQTZLEZ-UHFFFAOYSA-N
Pubchem ID :	16217468

Safety of [ 900174-60-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319
Precautionary Statements:	P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313

Application In Synthesis of [ 900174-60-9 ]

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

Downstream synthetic route of [ 900174-60-9 ]

[ 900174-60-9 ] Synthesis Path-Downstream 1~31

1
[ 900174-60-9 ]
[ 900174-92-7 ]
[ 298-12-4 ]
2-(4-((tert-butoxycarbonyl)methyl)-3-fluorophenylamino)-2-(5-ethoxy-2-fluorophenyl)acetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	In 1,2-dichloro-ethane; at 100℃; for 0.166667h;Microwave irradiation;	[00295] A mixture of 77B (120 mg, 0.500 mmol), 5-ethoxy-2- fluorophenylboronic acid (146 mg, 0.793 mmol) and glyoxylic acid monohydrate (55 mg, 0.60 mmol) in 1,2-dichloroethane (4 niL) was heated at 100C for 10 min in a microwave. The reaction mixture was purified by silica gel chromatography (dichloromethane/methanol) to give 77C (0.181 g, 83%) as a brown oil. MS (ESI) m/z 437.3 (M+H)+.

References: [1]Patent: WO2006/76246,2006,A2 .Location in patent: Page/Page column 142.

2
[ 900174-60-9 ]
[ 745020-22-8 ]
[ 298-12-4 ]
[ 900174-59-6 ]

Yield	Reaction Conditions	Operation in experiment
25%	In N,N-dimethyl-formamide; acetonitrile; at 85℃; for 0.5h;Microwave irradiation;	[00219] A mixture of 5-etlioxy-2-fluorophenylboronic acid (43 mg, 0.23 mmol), IB (72 mg, 0.2 mmol) and glyoxylic acid monohydrate (21 mg, 0.23 mmol) in acetonitrile (0.7 mL) and DMF (0.07 mL) was heated at 850C for 30 min in a Microwave Reactor. The crude product was purified by flash column chromatography (CH2Cl2 : MeOH= 100 : 15) to give 28 mg (25%) of 3OA as a solid.1H NMR (400 MHz, Methanol-d4) δ ppm 1.14 (s, 18 H) 1.19 (t, J=6.81 Hz, 3 H) 3.83(q, J=7.03 Hz, 2 H) 5.39 (s, 1 H) 6.59 (d, J=2.20 Hz, 1 H) 6.70 - 6.77 (m, 1 H) 6.89 - 7.00 (m, 2 H) 7.16 (dd, J=9.23, 2.20 Hz, 1 H) 7.33 (d, J=5.71 Hz5 1 H) 7.52 (d, J=9.23 Hz, 1 H) 7.85 (s, 1 H) 7.91 (d, J=6.15 Hz, 1 H); LC-MS: 556 (M + H)+.
25%	In N,N-dimethyl-formamide; acetonitrile; at 85℃; for 0.5h;	A mixture of <strong>[900174-60-9]5-ethoxy-2-fluorophenylboronic acid</strong> (43 mg, 0.23 mmol), Intermediate 1 (72 mg, 0.2 mmol) and glyoxylic acid monohydrate (21 mg, 0.23 mmol) in acetonitrile (0.7 mL) and DMF (0.07 mL) was heated at 85 C. for 30 min in a Microwave Reactor. The crude product was purified by flash column chromatography (CH2Cl2:MeOH=100:15) to give 28 mg (25%) of 73A as a solid. 1H NMR (400 MHz, Methanol-d4) δ ppm 1.14 (s, 18 H) 1.19 (t, J=6.81 Hz, 3 H) 3.83 (q, J=7.03 Hz, 2 H) 5.39 (s, 1 H) 6.59 (d, J=2.20 Hz, 1 H) 6.70-6.77 (m, 1 H) 6.89-7.00 (m, 2 H) 7.16 (dd, J=9.23, 2.20 Hz, 1 H) 7.33 (d, J=5.71 Hz, 1 H) 7.52 (d, J=9.23 Hz, 1 H) 7.85 (s, 1 H) 7.91 (d, J=6.15 Hz, 1 H); LC MS 556 (M+H).

References: [1]Patent: WO2006/76246,2006,A2 .Location in patent: Page/Page column 96.
[2]Patent: US2007/3539,2007,A1 .Location in patent: Page/Page column 74.
[3]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 188 - 192.

3
[ 900174-60-9 ]
[ 1142224-45-0 ]
[ 1142226-22-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 23 - 90℃;	Methyl 2-(5,5-dimethyl-1-cyclopenten-1-yl)-5'-(ethyloxy)-2'-fluoro- l,l'-biphenyl-4-carboxylate (T25.1). To a stirred solution of methyl 3-(5,5- dimethylcyclopent-1-enyl)-4-(trifluoromethylsulfonyloxy)benzoate T3.5 (0.400 g, 1.1 mmol) in DMF (4.00 mL) at 23C was added <strong>[900174-60-9]5-ethoxy-2-fluorophenylboronic acid</strong> (0.29 g, 1.6 mmol, commercially available from Sigma-Aldrich, St. Louis, MO, USA), potassium carbonate (0.44 g, 3.2 mmol), and then tetrakis(triphenylphosphine)palladium (0.12 g, 0.11 mmol). The mixture was heated to 90 C and stirred for 21 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 T25.1 as a colorless oil (0.350 g, 90% yield).
90%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 23 - 90℃; for 21h;	Methyl 2-(5,5-dimethyl-1-cyclopenten-1-yl)-5'-(ethyIoxy)-2f-fluoro- l,l'-biphenyl-4-carboxylate (T16.1). To a stirred solution of methyl 3-(5,5- dimethylcyclopent-1-enyl)-4-(trifluoromethylsulfonyloxy)benzoate T6.9 (0.400 g, 1.1 mmol) in DMF (4.00 mL) at 23C was added <strong>[900174-60-9]5-ethoxy-2-fluorophenylboronic acid</strong> (0.29 <n="193"/>g, 1.6 mmol, commercially available from Aldrich), potassium carbonate (0.44 g, 3.2 mmol), and then tetrakis(triphenylphosphine)palladium (0.12 g, 0.11 mmol). The mixture was heated to 90 C and stirred for 21 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 T16.1 as a colorless oil (0.350 g, 90% yield).

References: [1]Patent: WO2010/45258,2010,A2 .Location in patent: Page/Page column 206; 207.
[2]Patent: WO2009/111056,2009,A1 .Location in patent: Page/Page column 190-191.

4
[ 900174-60-9 ]
[ 1224883-40-2 ]
[ 1224883-55-9 ]

References: [1]Bioorganic and medicinal chemistry letters,2012,vol. 22,p. 5876 - 5884,9.

5
[ 900174-60-9 ]
[ 1520082-91-0 ]

References: [1]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 188 - 192.

6
[ 900174-60-9 ]
C₄₆H₅₆FN₅O₁₂S [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 188 - 192.

7
[ 900174-60-9 ]
methyl 3-((R)-1-((R)-2-(1-aminoisoquinolin-6-ylamino)-2-(5-ethoxy-2-fluorophenyl)acetyl)pyrrolidin-2-yl)-4-(isopropylsulfonyl)phenylcarbamate trifluoroacetic acid salt [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 188 - 192.

8
[ 900174-60-9 ]
(2R,3S)-methyl 2-(5-acetamido-2-(isopropylsulfonyl)phenyl)-1-((R)-2-(1-aminoisoquinolin-6-ylamino)-2-(5-ethoxy-2-fluorophenyl)acetyl)pyrrolidine-3-carboxylate trifluoroacetic acid salt [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 188 - 192.

9
[ 900174-60-9 ]
(2R,3S)-1-((R)-2-(1-aminoisoquinolin-6-ylamino)-2-(5-ethoxy-2-fluorophenyl)acetyl)-2-(2-(isopropylsulfonyl)-5-(methoxycarbonyl)phenyl)-pyrrolidine-3-carboxylic acid trifluoroacetic acid salt [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 188 - 192.

10
[ 900174-60-9 ]
[ 1569320-04-2 ]
[ 1569319-76-1 ]

Yield	Reaction Conditions	Operation in experiment
20 mg	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,2-dimethoxyethane; water; at 90℃; for 0.666667h;Microwave irradiation; Inert atmosphere;	2-(5-Bromo-pyridin-3-ylamino)-2-phenyl-acetamide (60 mg, 0.2 mmol), 5-ethoxy-2- fluorophenylboronic acid (48 mg, 0.26 mmol), tetrakis(triphenylphosphine)-palladium (11 mg, 0.01 mmol) and potassium carbonate (81 mg, 0.6 mmol) were added into a 10 mL microwave vial containing a magnetic stirrer bar, followed by DME (1 mL) and H20 (0.2 mL). The vessel was sealed with a cap under an argon atmosphere, and then the resulting mixture was heated to 90 C for 40 mins under microwave. The mixture was cooled to room temperature and diluted with water (5 mL), extracted with ethyl acetate (10 mL x 3), the combined organic layers were washed with brine (10 mL), dried over anhydrous sodium sulfate, concentrated in vacuo to give crude product. The crude product was purified by C-18 reversed phase HPLC column to give desired 2-[5-(5-ethoxy-2-fluoro-phenyl)-pyridin-3-ylamino]-2-phenyl-acetamide (20 mg) as a white solid.
20 mg	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,2-dimethoxyethane; water; at 90℃; for 0.666667h;Microwave irradiation; Inert atmosphere;	2-(5-Bromo-pyridin-3-ylamino)-2-phenyl-acetamide (60 mg, 0.2 mmol), <strong>[900174-60-9]5-ethoxy-2-fluorophenylboronic acid</strong> (48 mg, 0.26 mmol), tetrakis(triphenylphosphine)-palladium (11 mg, 0.01 mmol) and potassium carbonate (81 mg, 0.6 mmol) were added into a 10 mL microwave vial containing a magnetic stirrer bar, followed by DME (1 mL) and H2O (0.2 mL). The vessel was sealed with a cap under an argon atmosphere, and then the resulting mixture was heated to 90 C. for 40 mins under microwave. The mixture was cooled to room temperature and diluted with water (5 mL), extracted with ethyl acetate (10 mL*3), the combined organic layers were washed with brine (10 mL), dried over anhydrous sodium sulfate, concentrated in vacuo to give crude product. The crude product was purified by C-18 reversed phase HPLC column to give desired 2-[5-(5-ethoxy-2-fluoro-phenyl)-pyridin-3-ylamino]-2-phenyl-acetamide (20 mg) as a white solid.

References: [1]Patent: WO2014/29726,2014,A1 .Location in patent: Page/Page column 27.
[2]Patent: US2015/158815,2015,A1 .Location in patent: Paragraph 0185.

11
[ 900174-60-9 ]
[ 1610034-12-2 ]

References: [1]Patent: WO2014/78609,2014,A1 .
[2]Patent: US9133163,2015,B2 .

12
[ 900174-60-9 ]
(3,4-cis)-1-(5-ethoxy-2-fluorophenyl)-3-ethylpiperidin-4-ol [ No CAS ]
(3,4-trans)-1-(5-ethoxy-2-fluorophenyl)-3-ethylpiperidin-4-ol [ No CAS ]

References: [1]Patent: WO2014/78609,2014,A1 .

13
[ 900174-60-9 ]
2-((2R,4R)-4-(difluoromethoxy)-1-(4-(((3,4-trans)-1-(5-ethoxy-2-fluorophenyl)-3-methylpiperidin-4-yl)oxy)phenyl)pyrrolidin-2-yl)acetic acid trifluoroacetate [ No CAS ]

References: [1]Patent: WO2014/78609,2014,A1 .

14
[ 900174-60-9 ]
[ 1190075-01-4 ]

Yield	Reaction Conditions	Operation in experiment
48%	With copper(I) oxide; ammonium hydroxide; In methanol; water; for 7h;	[00300j 43E. 5-Ethoxy-2-fluoroaniline: To a solution of (5-ethoxy-2- fluorophenyl)boronic acid (10.1 g, 55.0 mmol) in MeOH (220 mL) was added 14.8 M aq.NH4OH (18.6 mL, 275 mmol) and cuprous oxide (1.57 g, 11.0 mmol). The reaction mixture was stirred under air for 7 h. The reaction mixture was concentrated. The crude product was dissolved in EtOAc/hexanes (2:1). The material was filtered through CELITE and concentrated. The crude material was purified by silica chromatography to provide 43E (4.10 g, 26.4 mmol, 48% yield) as a brown oil. LC-MS Anal. Calc’d for C8H20FNO: 155.17, found [M+H] 156.1. ‘HNMR(400 MHz, CDC13) ö 6.86 (dd,J=10.9, 8.8 Hz, 1H), 6.32 (dd, J=7.5, 2.9 Hz, 1H), 6.20 (dt, J=8.8, 3.3 Hz, 1H), 3.94 (q, J=6.9 Hz, 2H), 3.68 (br. s, 2H), 1.37 (t, J=6.9 Hz, 3H).
48%	With copper(I) oxide; ammonium hydroxide; In methanol; water; for 7h;	29A. 5-Ethoxy-2-fluoroaniline To a solution of (5-ethoxy-2-fluorophenyl)boronic acid (10.1 g, 55.0 mmol) in MeOH (220 mL) was added 14.8 M aqueous NH4OH (18.6 mL, 275 mmol), and then cuprous oxide (1.57 g, 11.0 mmol). The reaction mixture was stirred under air for 7 h. The reaction mixture was concentrated. The crude material was dissolved in EtOAc/Hex (2:1). The material was filtered through CELITE and concentrated. The crude material was purified by flash chromatography to provide 5-ethoxy-2-fluoroaniline (4.10 g, 26.4 mmol, 48% yield) as a brown oil. LC-MS Anal. Calc'd for C8H20FNO 155.17. found [M+H] 156.1. 1H NMR (400 MHz, CDCl3) δ 6.86 (dd, J=10.9, 8.8 Hz, 1H), 6.32 (dd, J=7.5, 2.9 Hz, 1H), 6.20 (dt, J=8.8, 3.3 Hz, 1H), 3.94 (q, J=6.9 Hz, 2H), 3.68 (br. s., 2H), 1.37 (t, J=6.9 Hz, 3H).
48%	With copper(I) oxide; ammonium hydroxide; In methanol; for 7h;	To a solution of (5-ethoxy-2-fluorophenyl) boronic acid (10.1 g, 55.0 mmol) in MeOH (220 mL) was added 14.8 M aq. NH4OH (18.6 mL, 275 mmol) and then cuprous oxide (1.57 g, 11.0 mmol). The reaction mixture was stirred under air for 7 h. The reaction mixture was concentrated. The crude product was dissolved in EtOAc/hexanes (2: 1). The material was filtered through CELITE and concentrated. The crude material was purified by silica chromatography to provide 9A (4.10 g, 26.4 mmol, 48% yield) as a brown oil. LC-MS Anal. Calc'd for C8Hi0FNO: 155.17, found [M+H] 156.1. 1H NMR (400 MHz, CDC13) δ 6.86 (dd, J=10.9, 8.8 Hz, IH), 6.32 (dd, J=7.5, 2.9 Hz, IH), 6.20 (dt, J=8.8, 3.3 Hz, IH), 3.94 (q, J=6.9 Hz, 2H), 3.68 (br. s, 2H), 1.37 (t, J=6.9 Hz, 3H).

References: [1]Patent: WO2014/78609,2014,A1 .Location in patent: Paragraph 00300.
[2]Patent: US9133163,2015,B2 .Location in patent: Page/Page column 63.
[3]Patent: WO2015/171722,2015,A1 .Location in patent: Page/Page column 91; 92.
[4]Journal of Medicinal Chemistry,2018,vol. 61,p. 681 - 694.

15
[ 900174-60-9 ]
[ 1610034-42-8 ]

References: [1]Patent: WO2014/78609,2014,A1 .
[2]Patent: US9133163,2015,B2 .
[3]Patent: WO2015/171722,2015,A1 .
[4]Journal of Medicinal Chemistry,2018,vol. 61,p. 681 - 694.

16
[ 900174-60-9 ]
(3,4-cis)-1-(5-ethoxy-2-fluorophenyl)-3-ethylpiperidin-4-ol [ No CAS ]

References: [1]Patent: WO2014/78609,2014,A1 .

17
[ 900174-60-9 ]
[ 1610034-44-0 ]

References: [1]Patent: WO2014/78609,2014,A1 .

18
[ 900174-60-9 ]
[ 1610036-16-2 ]

References: [1]Patent: WO2014/78609,2014,A1 .

19
[ 873-32-5 ]
[ 900174-60-9 ]
5'-ethoxy-2'-fluorobiphenyl-2-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%		No. I.7-10: 2-Ethoxyphenanthridin-6(5H)-one Under argon, <strong>[900174-60-9]5-ethoxy-2-fluorophenylboronic acid</strong> (300 mg, 1.63 mmol), potassium phosphate (433 mg, 2.04 mmol) and tetrakis(triphenylphosphine)palladium(0) (57 mg, 0.05 mmol) were dissolved in abs. N,N-dimethylformamide (8 ml), and the mixture was stirred at room temperature for 5 minutes. 2-Chlorobenzonitrile (112 mg, 0.82 mmol) was then added, and the reaction mixture was stirred at 160 C. for 4 h. After cooling to room temperature, water (>100 ml) was added and the aqueous phase was repeatedly extracted thoroughly with ethyl acetate. The combined organic phases were dried over magnesium sulphate, filtered off and concentrated under reduced pressure. Purification of the residue that remained by column chromatography (gradient ethyl acetate/n-heptane) gave 5'-ethoxy-2'-fluorobiphenyl-2-carbonitrile (150 mg, 76% of theory) in the form of a colourless solid. 5'-Ethoxy-2'-fluorobiphenyl-2-carbonitrile (150 mg, 0.62 mmol) was then dissolved in methanol (5 ml), finely powdered potassium hydroxide (174 mg, 3.10 mmol) was added and the mixture was stirred under reflux conditions for 2 h. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure, water was added and the resulting precipitated solid was filtered off and dried. This gave 2-ethoxyphenanthridin-6(5H)-one (72 mg, 46% of theory) as a colourless solid. 1H-NMR (400 MHz, d6-DMSO δ, ppm) 11.58 (br. s, 1H, NH), 8.56 (d, 1H), 8.32 (d, 1H), 7.86 (d, 1H), 7.82 (dd, 1H), 7.64 (dd, 1H), 7.29 (d, 1H), 7.13 (dd, 1H), 4.17 (q, 2H), 1.39 (t, 3H).

References: [1]Patent: US2014/302987,2014,A1 .Location in patent: Paragraph 0221-022.

20
[ 873-32-5 ]
[ 900174-60-9 ]
2-ethoxyphenanthridin-6(5H)-one [ No CAS ]

References: [1]Patent: US2014/302987,2014,A1 .

21
[ 900174-60-9 ]
methyl 2-((4S,5S)-1-(4-(((3R,4R)-1-(5-ethoxy-2-fluorophenyl)-3-methylpiperidin-4-yl)oxy)phenyl)-4-methyl-3-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-5-yl)acetate [ No CAS ]