Palladium-Catalyzed Arylation of Aromatic Amides Directed by a [4-Chloro-2-(1H-pyrazol-1-yl)phenyl]amine Auxiliary

Ya-Hua Hu; Zhi Xu; Ling-Yan Shao; Ya-Fei Ji

doi:10.1055/s-0037-1609558

Synlett, Inhaltsverzeichnis

Synlett 2018; 29(14): 1875-1880
DOI: 10.1055/s-0037-1609558

letter

Palladium-Catalyzed Arylation of Aromatic Amides Directed by a [4-Chloro-2-(1H-pyrazol-1-yl)phenyl]amine Auxiliary

Ya-Hua Hu ◊

School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. of China eMail: jyf@ecust.edu.cn

,

Zhi Xu ◊

School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. of China eMail: jyf@ecust.edu.cn

,

Ling-Yan Shao

School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. of China eMail: jyf@ecust.edu.cn

,

Ya-Fei Ji*

School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. of China eMail: jyf@ecust.edu.cn

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

^◊ Ya-Hua Hu and Zhi Xu are equal first authors.

Abstract

A palladium-catalyzed ortho-arylation of aromatic amides directed by [4-chloro-2-(1H-pyrazol-1-yl)phenyl]amine as a bidentate auxiliary has been established. The reaction is characterized by normal working conditions, a broad substrate scope, and a wide functional-group tolerance. In particular, the protocol is compatible with highly sterically demanding ortho-substituted anilides and aryl iodide partners, with good yields.

Key words

C–H activation - arylation - amides - directing groups - palladium catalysis - biaryls

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Referenzen

References and Notes

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9 Products 3 and 4; General Procedure A mixture of substrate 1 (0.3 mmol), (het)aryl iodide 2 (0.9 mmol), Pd(OAc)₂ (6.7 mg, 10 mol%), and Ag₃PO₄ (125.6 mg, 1.0 equiv) in p-xylene (2.5 mL) was stirred and then heated at 120 °C for 12 h. Upon completion of the reaction, the mixture was cooled to r.t. and filtered through a pad of Celite. The filtrate was washed with EtOAc (3 × 15 mL) and the organic layers were combined, dried (MgSO₄), and concentrated in vacuo to provide a crude product that was purified by column chromatography [silica gel, PE–EtOAc (40:1)] to give the desired product 3 or 4. N-[4-Chloro-2-(1H-pyrazol-1-yl)phenyl]-4′-methoxy-3-methylbiphenyl-2-carboxamide (3f) Yellow oil; yield: 106 mg (85%). ¹H NMR (400 MHz, CDCl₃): δ = 9.94 (s, 1 H), 8.43 (d, J = 8.8 Hz, 1 H), 7.57 (d, J = 1.6 Hz, 1 H), 7.54 (d, J = 2.8 Hz, 1 H), 7.33 (t, J = 7.6 Hz, 1 H), 7.30 (dd, J ₁ = 8.0, J ₂ = 2.4 Hz, 1 H), 7.19–7.23 (m, 3 H), 7.19 (d, J = 4.0 Hz, 1 H), 7.17 (d, J = 8.4 Hz, 1 H), 6.70 (d, J = 8.8 Hz, 2 H), 6.39 (t, J = 2.4 Hz, 1 H), 3.73 (s, 3 H), 2.40 (s, 3 H). ¹³C NMR (100 MHz, CDCl₃): δ = 168.5, 158.7, 141.5 (2 C), 138.9, 136.4, 135.5, 132.5, 130.0, 129.9, 129.8, 129.4 (2 C), 129.2, 129.1, 127.7, 127.4, 124.4, 122.5, 113.7 (2 C), 107.5, 55.2, 19.5. HRMS (EI): m/z [M⁺] calcd for C₂₄H₂₀ClN₃O₂: 417.1244; found: 417.1243.

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