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
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 hewitt10 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
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