Synthesis of 2-phenyl indoxyls

Synthesis of 2-phenyl indoxyls 

ARKIVOC 2006 (xi) 37-46 pp. 37 - 46 

Synthesis of 2-phenylindoxyls
Michael C. Hewitt* and Liming Shao
Drug Discovery, Sepracor Inc., 84 Waterford Drive, Marlborough MA 01752, USA
E-mail: michael.hewitt@sepracor.com
http://www.arkat-usa.org/get-file/23564/


Michael hewitt






10 a  n=1
10a: HPLC Rt = 9.87 min,

1 H NMR (400 MHz, CDCl3)
7.66-7.60 (m, 4H),
7.41-7.37 (m, 3H),
7.11-7.05 (m, 2H),
4.10-4.04 (m, 2H), NCH2
3.69-3.63 (m, 1H), 1H OF OCH2
3.58-3.51 (m, 1H); 1H OF OCH2


13C NMR (100 MHz, CDCl3) 197.2,C=0,  163.9, 137.8, 136.0, 128.9, 128.4, 126.5, 125.7, 122.8, 122.6, 114.8, 99.6, 67.9, 50.1;

http://www.nmrdb.org/13c/index.shtml?v=v2.14.1  PREDICT 13 C NMR

http://www.nmrdb.org/cosy/index.shtml?v=v2.14.1 COSY

GC-MS 13.4 min, M+ 251.

Selected gHMBC couplings (see above): 200 → 7.62, 7.64; 164 → 3.65, 3.5, 7.64; 99 → 3.65, 4.05.



1H NMR PREDICTION BELOW

Michael hewitt

• www.linkedin.com/pub/michael-hewitt/4/580/bb8/en