[ CAS No. 900174-60-9 ] {[proInfo.proName]}

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Quality Control of [ 900174-60-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 900174-60-9 ]

SDS Specification

Alternatived Products of [ 900174-60-9 ]

Product Details of [ 900174-60-9 ]

CAS No. :	900174-60-9	MDL No. :	MFCD05664321
Formula :	C₈H₁₀BFO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ISJGNUFTQTZLEZ-UHFFFAOYSA-N
M.W :	183.97	Pubchem ID :	16217468
Synonyms :

Safety of [ 900174-60-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313	UN#:	N/A
Hazard Statements:	H315-H319	Packing Group:	N/A
GHS Pictogram:

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 1~10

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)+.

Reference： [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).

Reference： [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).

Reference： [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 ]

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

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