Preparation and reactions of 4-, 5-, and 6-methoxy substituted 3-lithioindoles and 3-indolylzinc derivatives

Authors
Amat, M Seffar, F Llor, N Bosch, J
Citation
M. Amat et al., Preparation and reactions of 4-, 5-, and 6-methoxy substituted 3-lithioindoles and 3-indolylzinc derivatives, SYNTHESIS-S, (2), 2001, pp. 267-275
Citations number
52
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
SYNTHESIS-STUTTGART
ISSN journal
00397881 → ACNP
Issue
2
Year of publication
2001
Pages
267 - 275
Database
ISI
SICI code
0039-7881(200102):2<267:PARO45>2.0.ZU;2-R
Abstract
The preparation of 4-, 5-, and 6-methoxy substituted 3-lithio-1-(trialkylsi lyl)indoles 4b-d by metalation of the corresponding 3-bromoindoles, and the ir reactions with iodomethane, DMF, ethylene oxide and aziridines are repor ted. Transmetalation of 3-lithioindoles 4b-d with ZnCl2 afforded 3-indolylz ine chlorides 11b-d, which underwent Pd(0)-catalyzed cross-coupling reactio ns with 2-halopyridines to give 4-, 5-, and 6-methoxy substituted 3-(2-pyri dyl)indoles.