Remarkably selective palladium-catalyzed amination process: Rapid assembly of multiamino based structures

Tetrahedron Letters

Volumn 39, Issue 20, 1998, Pages 3121-3124

  Hong, Yaping ^a   Senanayake, Chris H ^a   Xiang, Tingjian ^a   Vandenbossche, Charles P ^a   Tanoury, Gerald J ^a   Bakale, Roger P ^a   Wald, Stephen A ^a  

^a SUNOVION PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC AMINE; NORASTEMIZOLE; PALLADIUM; POLYAMINE;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; DRUG DESIGN; LIGAND BINDING; METAL BINDING; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032516312     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00517-6     Document Type: Article

References (12)

1. (1) (a) Wolfe, J. P.; Wagaw, S.; Buchwald, L. S. J Am. Chem. Soc. 1996, 118, 7215.
2. (b) Wagaw, S.; Buchwald, L. S. J. Org. Chem. 1996, 61, 7240.
3. (c) Wolfe, J. P.; Buchwald, L. S. J. Org. Chem. 1996, 61, 1133.
4. (2) (a) Paul, F.; Patt, J.; Hartwig, J. F. J. Am. Chem. Soc. 1994, 116, 5969.
5. (b) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 4708.
6. (c) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 7217.
7. (3) Togni, A.; Venanzi, L. M. Ang. Chem., Int. Ed. Eng. 1994, 33, 497.
8. (4) Hong, Y.; Tanoury, G. T.; Wilkinson, H. S.; Bakale, R. P.; Wald, S. A.; Senanayake, C. H. Tetrahedron Lett. 1997, 38, 5607.
9. 4 and concentrated in vacuo. Silica gel column chromatography was performed using EtOAc:MeOH (8:2, v/v) to afford the desired product in 81% yield (see Table 2, Entry 3).
10. (6) Chen, S.; Junda, K.D. J. Am. Chem. Soc. 1997, 119, 8724.
11. 2O (0.11 g) with stirring. The resulting mixture was heated at 55 °C for 3 h (monitored by HPLC). After cooling to 0-5 °C, NaH ( 100 mg, 60% ) was added and stirred for 10 min. Heptane (100 mL) was added and stirred for 10 min at 0-10 °C. The mixture was passed through a pad of silica gel to remove insolubles. The filtrate was concentrated under vacuum at 30-40 °C to provide crude product, which was dried at 30-40 °C/5-10 mmHg for 10 h to afford 5 g of the desired prodcut 14 in essentially quantitative yield.
12. (8) Under thermal conditions the coupling was sluggish, and the THP group was partially cleaved to provide a mixture of 15, THP deprotected 15, 14, THP deprotected 14, and the corresponding urea analogue.