No renderable structure data available
FC1=CC=C(C(=O)OC)C(B(O)O)=C1Chemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 5-FLUORO-2-METHOXYCARBONYLPHENYLBORONIC ACID |
|---|---|
| IUPAC Name | — |
| CAS Number | 850568-05-7 |
| Database ID | 4374269 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
5-FLUORO-2-METHOXYCARBONYLPHENYLBORONIC ACID (CAS 850568-05-7) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 4374269
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-7ac0847d974043b3b3cb1e0f03baf611Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 5-Fluoro-2-(methoxycarbonyl)phenylboronic acid (1.00 g), benzyl bromide (0.50 mL), K2CO3 (1.75 g), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (PdCl2(dppf)) (0.17 g) were stirred in tetrahydrofuran (20 mL) at 60° C. for 24 hours. The reaction mixture was chromatographed on silica gel with 2% ethyl acetate/hexanes. The reaction mixture was chromatographed on silica gel with 2% ethyl acetate/hexanes
Source ID: ord-db7e34dd6a7a4c1899b00b02ced84e4aConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 5-Fluoro-2-(methoxycarbonyl)phenylboronic acid (1.00 g), 2-(phenylthio)isoindoline-1,3-dione (0.86 g), and (2-hydroxy-3,5-diisopropylbenzoyloxy)copper (0.29 g) were stirred in dioxane (15 mL) at 50° C. for 24 hours. The reaction mixture was chromatographed on silica gel with 5% ethyl acetate/hexanes. The reaction mixture was chromatographed on silica gel with 5% ethyl acetate/hexanes
Source ID: ord-5d6defc25b3c41e3a77ac7ed416445c2Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 5-Fluoro-2-(methoxycarbonyl)phenylboronic acid (1.00 g), 2-(phenylthio)isoindoline-1,3-dione (0.86 g), and (2-hydroxy-3,5-diisopropylbenzoyloxy)copper (0.29 g) were stirred in dioxane (15 mL) at 50° C. for 24 hours. The reaction mixture was chromatographed on silica gel with 5% ethyl acetate/hexanes. The reaction mixture was chromatographed on silica gel with 5% ethyl acetate/hexanes
Source ID: ord-5d6defc25b3c41e3a77ac7ed416445c2Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The title compound was synthesized according to the procedure described for the preparation of Example 1 using 4-chloro-3-iodopyridin-2-amine (1.20 g, 4.72 mmol) and 5-fluoro-2-methoxycarbonylphenylboronic acid (1.03 g, 5.19 mmol) to provide 410 (250 mg, 21% yield) as a solid. LC-MS (M+H=249, obsd.=249). The title compound was synthesized
Source ID: ord-4fc0e2d2e2c14e918ad31f629431d5b2Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 2-Amino-3-bromopyridine (87 mg, 0.50 mmol), 5-fluoro-2-methoxycarbonylphenylboronic acid (149 mg, 0.75 mmol), palladium(II) acetate (5 mg, 0.02 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (16 mg, 0.04 mmol), and potassium carbonate (207 mg, 1.50 mmol) were dissolved in dioxane/H2O (1.65 mL, 10/1, v/v), and stirred overnight at 100° C. The reaction mixture was concentrated, suspended in EtOAc/H2O, and filtered. The precipitate was washed with EtOAc/H2O, and dried under vacuum to provide 3 (35 mg, 33% yield) as a solid. LC-MS (M+H=215, obsd.=215). 1H NMR (400 MHz, d6-DMSO): δ 12.12 (s, 1H), 8.84 (d, 1H), 8.53 (d, 1H), 8.43 (d, 1H), 8.38 (dd, 1H), 7.53 (t, 1H), 7.33 (dd, 1H). The reaction mixture was concentrated filtered The precipitate was washed with EtOAc/H2O dried under vacuum
Source ID: ord-93e1057d3cc4487d9d036dd28fff8528Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 5-Fluoro-2-(methoxycarbonyl)phenylboronic acid (1.00 g), benzyl bromide (0.50 mL), K2CO3 (1.75 g), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (PdCl2(dppf)) (0.17 g) were stirred in tetrahydrofuran (20 mL) at 60° C. for 24 hours. The reaction mixture was chromatographed on silica gel with 2% ethyl acetate/hexanes. The reaction mixture was chromatographed on silica gel with 2% ethyl acetate/hexanes
Source ID: ord-353048824e734bd6acd84d0e4a301db0Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 5-Fluoro-2-(methoxycarbonyl)phenylboronic acid (1.00 g), benzyl bromide (0.50 mL), K2CO3 (1.75 g), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (PdCl2(dppf)) (0.17 g) were stirred in tetrahydrofuran (20 mL) at 60° C. for 24 hours. The reaction mixture was chromatographed on silica gel with 2% ethyl acetate/hexanes. The reaction mixture was chromatographed on silica gel with 2% ethyl acetate/hexanes
Source ID: ord-353048824e734bd6acd84d0e4a301db0Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 5-Fluoro-2-(methoxycarbonyl)phenylboronic acid (1.00 g), 2-(phenylthio)isoindoline-1,3-dione (0.86 g), and (2-hydroxy-3,5-diisopropylbenzoyloxy)copper (0.29 g) were stirred in dioxane (15 mL) at 50° C. for 24 hours.
Source ID: ord-32031f97c65543f4bb9e66761d5a355eConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-7ac0847d974043b3b3cb1e0f03baf611Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 5-Fluoro-2-(methoxycarbonyl)phenylboronic acid (1.00 g), benzyl bromide (0.50 mL), K2CO3 (1.75 g), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (PdCl2(dppf)) (0.17 g) were stirred in tetrahydrofuran (20 mL) at 60° C. for 24 hours. The reaction mixture was chromatographed on silica gel with 2% ethyl acetate/hexanes. The reaction mixture was chromatographed on silica gel with 2% ethyl acetate/hexanes
Source ID: ord-75f72bcb67de4d22b39b09faf9df0113Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 5-Fluoro-2-(methoxycarbonyl)phenylboronic acid (1.00 g), benzyl bromide (0.50 mL), K2CO3 (1.75 g), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (PdCl2(dppf)) (0.17 g) were stirred in tetrahydrofuran (20 mL) at 60° C. for 24 hours. The reaction mixture was chromatographed on silica gel with 2% ethyl acetate/hexanes. The reaction mixture was chromatographed on silica gel with 2% ethyl acetate/hexanes
Source ID: ord-75f72bcb67de4d22b39b09faf9df0113PubChem References
These sources are listed in the compound's public database record.
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