Pd(0)-Catalyzed Direct Inter- and Intramolecular C–H Functionalization of 4-Carboxyimidazoles

Steven Frippiat; Antoine Peresson; Thibaut Perse; Yvan Ramondenc; Cédric Schneider; Olivier Querolle; Patrick Angibaud; Virginie Poncelet; Lieven Meerpoel; Vincent Levacher; Laurent Bischoff; Christine Baudequin; Christophe Hoarau

doi:10.1055/s-0040-1708003

Synlett, Inhaltsverzeichnis

Synlett 2020; 31(10): 1015-1021
DOI: 10.1055/s-0040-1708003

letter

Pd(0)-Catalyzed Direct Inter- and Intramolecular C–H Functionalization of 4-Carboxyimidazoles

Authors

Steven Frippiat‡

^aNormandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France eMail: christine.baudequin@univ-rouen.fr eMail: christophe.hoarau@insa-rouen.fr
Antoine Peresson

^aNormandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France eMail: christine.baudequin@univ-rouen.fr eMail: christophe.hoarau@insa-rouen.fr
Thibaut Perse

^bJanssen Research & Development, Division of Janssen-Cilag S.A. Campus de Maigremont, BP615, 27106 Val de Reuil Cedex, France
Yvan Ramondenc

^aNormandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France eMail: christine.baudequin@univ-rouen.fr eMail: christophe.hoarau@insa-rouen.fr
Cédric Schneider

^aNormandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France eMail: christine.baudequin@univ-rouen.fr eMail: christophe.hoarau@insa-rouen.fr
Olivier Querolle

^bJanssen Research & Development, Division of Janssen-Cilag S.A. Campus de Maigremont, BP615, 27106 Val de Reuil Cedex, France
Patrick Angibaud

^bJanssen Research & Development, Division of Janssen-Cilag S.A. Campus de Maigremont, BP615, 27106 Val de Reuil Cedex, France
Virginie Poncelet

^bJanssen Research & Development, Division of Janssen-Cilag S.A. Campus de Maigremont, BP615, 27106 Val de Reuil Cedex, France
Lieven Meerpoel

^cJanssen Research & Development, Division of Janssen-Cilag a division of Janssen Pharmaceutica NV, Turnhoutseweg 30, 2340 Beerse, Belgium
Vincent Levacher

^aNormandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France eMail: christine.baudequin@univ-rouen.fr eMail: christophe.hoarau@insa-rouen.fr
Laurent Bischoff

^aNormandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France eMail: christine.baudequin@univ-rouen.fr eMail: christophe.hoarau@insa-rouen.fr
Christine Baudequin∗

^aNormandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France eMail: christine.baudequin@univ-rouen.fr eMail: christophe.hoarau@insa-rouen.fr
Christophe Hoarau∗

^aNormandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France eMail: christine.baudequin@univ-rouen.fr eMail: christophe.hoarau@insa-rouen.fr

Abstract

Alle Artikel dieser Rubrik

Abstract

The palladium-catalyzed arylation and alkenylation of N-substituted methyl imidazole-4-carboxylates are described through inter- and intramolecular pathways. Both direct C2–H and C5–H arylation and alkenylation proceed under Pd(0)/Cu(I) cooperative catalysis and Pd(0) catalysis, respectively, in low-polarity 1,4-dioxane solvent. The methodology gives access to C2 (hetero)aryl or alkenyl imidazoles as well as innovative C2- and C5-arylated fused imidazoles tricycles with a five- to seven-membered middle ring.

Key words

C–H functionalization - palladium catalysis - imidazole - arylation - alkenylation

Volltext

Referenzen

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21 See the Supporting Information for more details.
22 General Procedure for Pd-Catalyzed Intermolecular Direct C2–H Arylation of Methyl N-Benzyl-1H-imidazole 4-carboxylate under Thermic ConditionsMethyl 1-benzyl-1H-imidazole-4-carboxylate (1a, 80 mg, 0.37 mmol, 1 equiv), the requisite halide 2 (1.2 equiv), Pd(OAc)₂ (18 μmol, 5 mol%), PPh₃ (37 μmol, 10 mol%), CuI (0.74 mmol, 2 equiv), and anhydrous DBU (0.74 mmol, 2 equiv) were placed in a dry sealed tube containing a magnetic stir bar. The tube was evacuated and back-filled with nitrogen three times before adding anhydrous 1,4-dioxane (2.5 mL). The tube was sealed and heated to 140 °C for 18 h. The reaction was filtered through a Celite^® pad (washing with DCM and EtOAc). The solvents were removed under reduced pressure, and the crude product was then purified by column chromatography (DCM to DCM/EtOAc, 9:1).
23 Compound 3a was prepared according to the general procedure. The crude product was purified by flash chromatography to afford 3a in 76% yield using the aryl bromide and 95% yield using the aryl iodide as a pale yellow solid; mp 89–90 °C. ¹H NMR (300 MHz, CDCl₃): δ = 7.64 (s, 1 H_im, H5), 7.46 (d, J = 8.0 Hz, 2 H_arom), 7.35–7.33 (m, 3 H_benzyl), 7.22 (d, J = 8.0 Hz, 2 H_arom), 7.09–7.07 (m, 2 H_benzyl), 5.19 (s, 2 H), 3.89 (s, 3 H, OMe), 2.38 (s, 3 H, CH₃). ¹³C NMR (75 MHz, CDCl₃): δ = 163.5 (C=O), 149.5 (C2, Cq_im), 139.7 (C4′, Cq_arom), 135.9 (C1′, Cq_benzyl), 132.9 (C4_im, Cq), 129.3 (2 × CH), 129.2 (2 × CH), 129.1 (2 × CH), 128.4 (CH_benzyl), 127.1 (C5, CH_im), 126.9 (2 × CH_benzyl), 126.5 (Cq), 51.8 (OCH₃), 51.0 (NCH₂), 21.4 (CH₃). IR (ATR): 3125, 3079, 2920, 2850, 1689, 1549, 1330, 1227, 1004, 725 cm^–1. HRMS: Anal. Calcd for C₁₉H₁₉N₂O₂ [M + H]⁺: 307.1447; found: 307.1455.

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Zusatzmaterial

Supporting Information (PDF)