The high-pressure S(N)AR reaction of N-p-fluorobenzyl-2- chlorobenzimidazole with amines; an approach to norastemizole and analogues

Tetrahedron Letters

Volumn 40, Issue 13, 1999, Pages 2439-2442

  Barrett, Ian C ^a   Kerr, Michael A ^a  

^a ACADIA UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; ASTEMIZOLE; IMIDAZOLE DERIVATIVE; N 4 FLUOROBENZYL 2 CHLOROBENZIMIDAZOLE; NORASTEMIZOLE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CHEMICAL STRUCTURE; HYPERBARISM; REACTION ANALYSIS; REACTION TIME;

EID: 0033605810     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00290-7     Document Type: Article

References (13)

1. For leading references concerning norastemizole, and the nucleophilic substitution of 2-chlorobenzimidazoles see: Hong, Y.; Tanoury, G.J.; Wilkinson, S.; Bakale, R.P.; Wald, S.A.; Senanayake, C.H. Tetrahedron Lett. 1997, 38, 5607-5610.
2. Janssens, F.E.; Hens, J.F.; Torremans, J.L.G.; Heykants, J.J.P. European Patent No. 0 232 937 B1, 1992.
3. a) Wolfe, J.P.; Buchwald, S.L. J. Am Chem. Soc. 1997, 119, 6054-6058.
4. b) Wolfe, J.P.; Buchwald, S.L. Tetrahedron Lett. 1997, 38, 6359-6362.
5. c) Ahman, J.; Buchwald, S.L. Tetrahedron Lett. 1997, 38, 6363-6366.
6. d) Wolfe, J.P.; Buchwald S.L. J. Org. Chem. 1997, 62, 6066-6068.
7. Isaacs, N.S., Chemical transformations. In: Holzapfel, W.P.; Isaacs, N.S., editors. High-Pressure Techniques in Chemistry and Physics. Oxford University Press. 1997, p 308.
8. 13 NMR, ms, and infrared spectra.
9. 3, brine and was dried over anhydrous magnesium sulfate. The solvent was removed in vacuo to give a residue which was purified by flash chromatography on silica gel (eluted with 50% EtOAc/hexanes). The yield was 194 mg (91%), as a white solid.
10. Ramachandran, P.S.; Kampf, J.W.; Rasmussen, P.G. J. Org. Chem. 1994, 59, 4341-4345.
11. Finger, G.C.; Starr, L.D.; Dickerson, D.R.; Gutowsky, H.S.; Hamer, J. J. Org. Chem. 1963, 28, 1666-1668.
12. See ref. 3 p 314.
13. See ref. 3 p 325.