Reaction #1904085

ord-eabae0b77ab347dab4981792cf9ce559

Reaction equation

CCC1(c2cccs2)OCC(=O)Nc2ccc(Br)cc21
7-bromo-5-ethyl-5-thien-2-yl-1,5-dihydro-4,1-benzoxazepin-2(3H)-one
OB(O)c1ccc(F)c(Cl)c1
3-chloro-4-fluorobenzeneboronic acid
CCC1(c2cccs2)OCC(=O)Nc2ccc(-c3ccc(F)c(Cl)c3)cc21
7-(3-Chloro-4-fluoro-phenyl)-5-ethyl-5-thiophen-2-yl-1,5-dihydro-benzo[e][1,4]oxazepin-2-one

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

Prepared from 7-bromo-5-ethyl-5-thien-2-yl-1,5-dihydro-4,1-benzoxazepin-2(3H)-one and 3-chloro-4-fluorobenzeneboronic acid using the coupling procedure described in example 1. 1H-NMR (DMSO-d6) δ 10.08 (s, 1H), 7.85 (dd, J=7.1, 2.2 Hz, 1H), 7.65 (m, 2H), 7.57 (dd, J=5.0, 1.0 Hz, 1H), 7.52 (m, 2H), 7.26 (d, J=8.5 Hz, 1H), 7.01 (m, 2H), 4.11 (d, J=15.4 Hz, 1H), 3.95 (d, J=15.4 Hz, 1H), 2.41 (m, 2H), 0.78 (t, J=7.0 Hz, 3H); MS (ES) m/z 400 (M−H)−.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07598237B2uspto-grants-2009_10