[ CAS No. 504437-66-5 ] {[proInfo.proName]}

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Quality Control of [ 504437-66-5 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 504437-66-5 ]

CAS No. :	504437-66-5	MDL No. :
Formula :	C₁₈H₂₄BFN₂O₅	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	378.20	Pubchem ID :	-
Synonyms :

Safety of [ 504437-66-5 ]

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Precautionary Statements:	P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330	UN#:
Hazard Statements:	H302-H315-H319	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 504437-66-5 ]

* 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 [ 504437-66-5 ]

[ 504437-66-5 ] Synthesis Path-Downstream 1~10

1
[ 504437-66-5 ]
[ 153747-97-8 ]
[ 1188335-25-2 ]

Yield	Reaction Conditions	Operation in experiment
69%	With potassium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In ethanol; N,N-dimethyl-formamide; toluene; at 90℃; for 1h;Inert atmosphere;	A mixture of tert- Butyl 4-(5-bromo-2-pyridinyl)-l-piperazinecarboxylate (0.203 g, 0.593 mmol) and7V-({(55)- 3-[3-fluoro-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl]-2-oxo-l,3-oxazolidin-5- yl}methyl)acetamide (0.270 g, 0.714 mmol) in dmf (4 niL), EtOH (1.5 niL), toluene (2.5 mL) and K2CO3 (1 mL, 2 M, 2 mmol) was purged with nitrogen. PdCl2(dppf) (24 mg, 0.03 mmol) was added and the mixture was heated to 900C under nitrogen for 1 h, then partitioned between EtOAc and water. Column chromatography (EtOAc) gave the titled compound (0.21O g, 69%) as a white solid. APCI MS m/z 514 (M + H). 1H NMR (400 MHz, DMSO-J6) delta 8.32 (bs, IH), 8.27 (t, J= 5.9 Hz, IH), 7.75 (ddd, J- 8.9, 2.4, 1.7 Hz, IH), 7.53-7.60 (m, 2H), 7.38 (dd, J- 8.6, 2.2 Hz, IH), 6.94 (d, J= 8.9 Hz, IH), 4.72-4.79 (m, IH), 4.15 (t, J= 9.1 Hz, IH), 3.77 (dd, J = 9.2, 6.5 Hz, IH), 3.52-3.57 (m, 4H), 3.40-3.46 (m, 6H), 1.84 (s, 3H), 1.43 (s, 9H).

Reference： [1]Patent: WO2009/120789,2009,A1 .Location in patent: Page/Page column 89

2
[ 504437-66-5 ]
[ 374930-88-8 ]
[ 1188335-18-3 ]

Yield	Reaction Conditions	Operation in experiment
81%	With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In ethanol; toluene; for 5h;Inert atmosphere; Reflux;	A mixture of tert- butyl 4-(5-bromo-2-pyrimidinyl)-l-piperazinecarboxylate (57 mg, 0.165 mmol) (prepared as described in US 2007/0149561 Al), N-{3-[3-fluoro-4-(4,4,5,5-tetramethyl- [l,3,2]dioxaborolan-2-yl)-phenyl]-2-oxo-oxazolidin-5-ylmethyl}acetamide (75 mg, 1.98 mmol) (prepared as described by Chen, S. et al: US Pat. No. US7129259 or Gravestock et. al. WO 2004/078753), PdCl2(dppf) (7.0 mg, 0.08 mmol) and 2N Na2CO3 (1.O mL , 2.00 mmol) in a mixture of toluene (5.0 mL) and ethanol (2.0 mL) was purged with nitrogen, then refluxed under an atmosphere of nitrogen for 5 h. The product was extracted with EtOAc and the extract was washed well with water, then worked up and chromatographed on silica. EtOAc eluted fore fractions, while MeOH/EtOAc (1 :19) eluted the title product as a cream solid (69.4 mg, 81%), APCI MS m/z 515.5 (M + H+); 1H NMR (400 MHz, DMSO) delta 8.59 (d, J=I.4 Hz, 2H), 8.22 (t,J=5.8 Hz, IH), 7.63-7.57 (m, 2H), 7.40 (dd,J=8.6, 2.1 Hz, IH), 4.80- 4.70 (m, IH), 4.16 (t, J=9.1 Hz, IH), 3.79-3.76 (m, 5H), 3.45-3.40 (m, 6H), 1.84 (s, 3H), 1.43 (s, 9H).

Reference： [1]Patent: WO2009/120789,2009,A1 .Location in patent: Page/Page column 85

3
[ 504437-66-5 ]
[ 6188-23-4 ]
[ 1202701-37-8 ]

Yield	Reaction Conditions	Operation in experiment
29%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; for 6h;Reflux;	(2) Preparation of (S)-n-((3-(3-fluoro-4-(imidazo[1,2-a]pyridine-6-yl)phenyl)-2-oxooxazolidine-5-yl)methyl)acetamide 172 mg of <strong>[6188-23-4]6-bromoimidazo[1,2-a]pyridine</strong> (4), 300 mg of (S)-n-((3-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)phenyl)-2-oxooxazolidine-5-yl)methyl)acetamide, 92 mg of tetrakis (triphenylphosphine)palladium (0) and 420 mg of sodium carbonate were suspended in 1,4-dioxane (3 mL) and water (0.3 mL), and the suspension was heated at reflux for 6 hours. The reaction mixture was poured into saturated aqueous NaHCO3, and extracted with ethyl acetate. After conventional workup, the resulting residue was washed with ethyl acetate to afford 85 mg of the titled compound as a brown powder (yield: 29%). LCMS (ESI) m/z (M+H)+: 368.93 1H-NMR (DMSO-d6) delta: 1.83 (3H, s), 3.41 (2H, t, J=5.7 Hz), 3.78 (1H, dd, J=8.7, 6.3 Hz), 4.17 (1H, t, J=8.7 Hz), 4.73-4.78 (1H, m), 7.39-7.45 (2H, m), 7.60-7.68 (3H, m), 7.99 (1H, s), 8.26 (1H, t, J=5.4 Hz), 8.79 (1H, s).

Reference： [1]Patent: US2011/98471,2011,A1 .Location in patent: Page/Page column 57

4
[ 504437-66-5 ]
[ 67625-37-0 ]
[ 1202701-43-6 ]

Yield	Reaction Conditions	Operation in experiment
74%	With potassium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In ethanol; water; toluene; for 4h;Reflux;	(2) Preparation of (S)-ethyl 6-(4-(5-(acetamidomethyl)-2-oxooxazolidine-3-yl)-2-fluorophenyl)imidazo[1,2-a]pyridine-2-carboxylate 4.00 g of <strong>[67625-37-0]ethyl 6-bromoimidazo[1,2-a]pyridine-2-carboxylate</strong> (5), 2.85 g of (S)-n-((3-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)phenyl)-2-oxooxazolidine-5-yl)methyl)acetamide, 0.542 g of PdCl2 (dppf) and 4.39 g of potassium carbonate were suspended in toluene (15 mL)-ethanol (15 mL)-water (5 mL), and the suspension was heated at reflux for 4 hours. The resulting precipitate was isolated and washed with water and ethyl acetate to afford 3.46 g of the titled compound as colorless powder (yield: 74%). LCMS (ESI) m/z (M+H)+: 441.10

Reference： [1]Patent: US2011/98471,2011,A1 .Location in patent: Page/Page column 57-58

5
[ 504437-66-5 ]
[ 7169-95-1 ]
[ 1202701-51-6 ]

Yield	Reaction Conditions	Operation in experiment
76%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 90 - 100℃; for 1h;	To boronic acid ester compound having acetamide side chain (15, 1.902 g), and 6-bromo-2-methyltriazolopyridine compound (14, 1.162 g) in dioxane (40 mL) and water (10 mL), Na2CO3 (1.85 g) and Pd(Ph3P)4 (588 mg) were added and the solution was stirred at 90 to 100 C. for 1 hour. Then, the solvent was removed under reduced pressure. The residue was dissolved in ethanol, and 1.246 g of colorless compound 16 precipitated. The mother liquid was purified by column chromatography (chloroform-methanol (9:1)). 223 mg of colorless compound 16 was precipitated from ethanol. Total: 1.469 g (76%).Compound 16: 1H-NMR (300 MHz, CDCl3-CD3OD (9:1)) 2.04 (s, 3H), 2.62 (s, 3H), 3.60-3.72 (m, 2H), 3.87 (dd, 9, 7, 1H), 4.14 (dd, 9, 9, 1H), 4.81-4.90 (m, 1H), 7.34 (dd, 8.5, 2, 1H), 7.49 (dd, 8.5, 8.5, 1H), 7.62 (dd, 13, 2, 1H), 7.66-7.75 (m, 2H), 8.69 (d, 1, 1H);LRMS m/z 383 (M+, 44), 339 (18), 311 (7), 280 (19), 255 (56), 242 (27), 158 (26), 85 (26), 73 (20), 56 (52), 43 (100).

Reference： [1]Patent: US2011/98471,2011,A1 .Location in patent: Page/Page column 59

6
[ 504437-66-5 ]
[ 288067-35-6 ]
(S)-N-((3-(4'-cyano-2-fluoro-3'-hydroxy-[1,1'-biphenyl]-4-yl)-2-oxooxazolidin-5-yl)methyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; ethanol; water; at 90 - 95℃; for 3h;Inert atmosphere;	General procedure: A mixture of the desired aryl boronic ester/ or acid (1 mmol) and the desired aryl bromide (1 mmol), Pd(dppf)2Cl2 (0.05 mmol) and K2CO3 (4 mmol) in dioxane (3 mL), EtOH (1 mL) and H2O ( 1 mL) was added to a nitrogen purged 25 mL flask. The mixture was heated to 90-95 C and stirred for 3 hrs. Then cooled to room temperature, filtrated and evaporated to dryness. Then the crude was dissolved in DMF (1 mL), and then it was purified by reversed phase column chromatography on prep- HPLC using gradient of (water/acetonitrile/ 0.1 %TFA). Those fractions containing pure product were pooled and lyophilized to give the pure products.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 5310 - 5321

7
[ 504437-66-5 ]
[ 112204-58-7 ]
(S)-N-((3-(2,4'-difluoro-3'-hydroxy-[1,1'-biphenyl]-4-yl)-2-oxooxazolidin-5-yl)methyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; ethanol; water; at 90 - 95℃; for 3h;Inert atmosphere;	General procedure: A mixture of the desired aryl boronic ester/ or acid (1 mmol) and the desired aryl bromide (1 mmol), Pd(dppf)2Cl2 (0.05 mmol) and K2CO3 (4 mmol) in dioxane (3 mL), EtOH (1 mL) and H2O ( 1 mL) was added to a nitrogen purged 25 mL flask. The mixture was heated to 90-95 C and stirred for 3 hrs. Then cooled to room temperature, filtrated and evaporated to dryness. Then the crude was dissolved in DMF (1 mL), and then it was purified by reversed phase column chromatography on prep- HPLC using gradient of (water/acetonitrile/ 0.1 %TFA). Those fractions containing pure product were pooled and lyophilized to give the pure products.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 5310 - 5321

8
[ 149524-42-5 ]
[ 504437-66-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 5310 - 5321

9
[ 504437-66-5 ]
[ 43192-33-2 ]
(S)-N-(3-(2-fluoro-3'-methoxy-4'-formylbiphenyl-4-yl)-2-oxo-1,3-oxazolidine-5-ylmethyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With bis-triphenylphosphine-palladium(II) chloride; In water; N,N-dimethyl-formamide; at 75℃; for 10h;Alkaline conditions; Inert atmosphere;	General procedure: To a well-stirred solution of intermediate 4 (2.0 g, 5.29 mmol)and sodium carbonate (2.24 g, 21.16 mmol) in DMF (20 mL) andwater (2 mL) was added 4-bromo-2-hydroxybenzaldehyde (1.06 g,5.29 mmol) and Pd(PPh3)2Cl2 (0.18 g, 0.26 mmol), then the mixturewas stirred at 75 C for 10 h under nitrogen. After completion of thereaction monitored by TLC, water (50 mL) was added and themixture was extracted with DCM (15mL 3) for three times. Theorganic phase was washed with brine and concentrated in vacuo toyield 5a as a white solid in 73% yield.

Reference： [1]European Journal of Medicinal Chemistry,2020,vol. 185

10
[ 504437-66-5 ]
[ 24078-12-4 ]
(S)-N-(3-((2-fluoro-3'-methyl-40-formyl)biphenyl-4-yl)-2-oxo-1,3-oxazolidine-5-ylmethyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With bis-triphenylphosphine-palladium(II) chloride; In water; N,N-dimethyl-formamide; at 75℃; for 10h;Alkaline conditions; Inert atmosphere;	General procedure: To a well-stirred solution of intermediate 4 (2.0 g, 5.29 mmol)and sodium carbonate (2.24 g, 21.16 mmol) in DMF (20 mL) andwater (2 mL) was added 4-bromo-2-hydroxybenzaldehyde (1.06 g,5.29 mmol) and Pd(PPh3)2Cl2 (0.18 g, 0.26 mmol), then the mixturewas stirred at 75 C for 10 h under nitrogen. After completion of thereaction monitored by TLC, water (50 mL) was added and themixture was extracted with DCM (15mL 3) for three times. Theorganic phase was washed with brine and concentrated in vacuo toyield 5a as a white solid in 73% yield.

Reference： [1]European Journal of Medicinal Chemistry,2020,vol. 185

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[ CAS No. 504437-66-5 ] {[proInfo.proName]}

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[ 504437-66-5 ] Synthesis Path-Downstream 1~10

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