Expeditious synthesis of 1,1-diarylethylenes related to isocombretastatin A-4 (isoCA-4) via palladium-catalyzed arylation of N-tosylhydrazones with aryl triflates

Tetrahedron Letters

Volumn 50, Issue 47, 2009, Pages 6549-6552

  Tréguier, Bret ^a   Hamze, Abdallah ^a   Provot, Olivier ^a   Brion, Jean Daniel ^a   Alami, Mouâd ^a  

^a UNIVERSITÉ PARIS SACLAY   (France)

Author keywords

1, 1 Diarylethylenes; Aryl triflates; Isocombretastatin A 4; Palladium Xphos ligand; Tosylhydrazones

Indexed keywords

ALKENE DERIVATIVE; ANTINEOPLASTIC AGENT; DIOXANE; HYDRAZONE DERIVATIVE; ISOCOMBRETASTATIN A4 DERIVATIVE; PALLADIUM; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; BARLUENGA REACTION; CATALYSIS; CROSS COUPLING REACTION; DRUG SYNTHESIS; REACTION OPTIMIZATION;

HYDRA;

EID: 77955550424     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.09.046     Document Type: Article

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39. General procedure for the synthesis of 1. To a dioxane (6 mL) solution of N-tosylhydrazone 2 (0.5 mmol), tBuOLi (1 mmol), Pd(OAc) 2 (0.025 mmol), and X-Phos (0.05 mmol) was added the aryl triflate 3 (0.5 mmol) in dioxane (2 mL). The reaction vessel was sealed, and then heated at 90 °C for 3 h. The resulting suspension was cooled to room temperature and filtered through a pad of Celite eluting with AcOEt, and the inorganic salts were removed. The filtrate was concentrated and purification of the residue by silica gel column chromatography gave the desired product. Diarylethylene 1a: Yield: 91%. Rf (cyclohexane/EtO Ac: 6/4) = 0.60. IR (crrr-1): 1579, 1507, 1454, 1411, 1346, 1299, 1233, 1174, 1122, 1030, 1004. 1H NMR: (δ ppm, CD3COCD3, 300 MHz): 3.75 (s, 3H, OCH3), 3.78 (s, 6H, OCH3), 3.82 (s, 3H, OCH3), 5.34 (m, 2H, CH2), 6.60 (s, 2H), 6.92 (d, 2H, J= 8.7 Hz), 7.29 (d, 2H, J= 8.7 Hz). 13C NMR (δ ppm, 75 MHz, CD3COCD3): 55.5, 56.4 (2), 60.5, 106.8 (2), 112.7, 114.4 (2), 130.1 (2), 134.4, 138.2 (2), 150.6, 154.1 (2), 160.5. Diarylethylene 1d: Yield: 69%. Rf (cyclohexane/EtOAc: 9/1) = 0.58. IR (cm-1): 1579, 1504, 1462, 1410, 1344, 1235, 1125, 1007. 1H NMR: (δ ppm, CDCl3, 300 MHz): 3.73 (s, 6H, OCH3), 3.80 (s, 3H, OCH3), 5.34 (d, 2H, J= 1.0 Hz, CH2), 6.44 (s, 2H, CH), 7.22 (s, 4H, CH). 13C NMR (δ ppm, 75 MHz, CDCl3): 56.1 (2), 60.9, 105.5 (2), 114.3, 128.4 (2), 129.6 (2), 133.7, 136.8, 137.8, 139.7, 149.0, 153.0 (2). Diarylethylene 1i: Yield: 75%. Rf (cyclohexane/EtOAc: 7/3) = 0.28. Mp: 143-145 °C. IR(cm-1): 1719, 1574, 1508, 1453, 1411, 1350, 1221, 1177, 1124, 996. 1H NMR: (δ ppm, CDCl3, 300 MHz): 3.82 (s, 6H), 3.89 (s, 3H), 5.54 (s, 1H), 5.56 (s, 1H), 6.42 (d, 1H, J = 9.5 Hz), 6.51 (s, 2H), 7.27 (dd, 1H, J = 1.6 Hz, J = 8.0 Hz), 7.35 (d, 1H, J = 1.5 Hz), 7.44 (d, 1H, J = 8.0 Hz), 7.71 (d, 1H, J = 9.5 Hz).13C NMR (δ ppm, 75 MHz, CDCl3): 56.0 (2), 60.8, 105.6 (2), 116.1, 116.2, 116.4, 118.2, 124.3, 127.4, 136.0, 138.1, 142.9, 145.1, 148.6, 153.0 (2), 153.9, 160.6.
40. The reaction was conducted according to the general method described above. The reaction vessel was sealed, then placed in the Emrys Optimizer and exposed to microwave irradiation according to the following specifications: temperature: 120 °C; time: 30 min; fixed hold time: on; sample absorption: high; pre-stirring: 60 s.