(3-Cyano-5-fluorophenyl)boronic acid → 3-Fluoro-5-(5-methyl-2-oxo-5-thien-2-yl-1,2,3,5-tetrahydro-4,1-benzoxazepin-7-yl)benzonitrile

HRID 1816914Notes

Reaction equation

HRID 1816914 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[CH2:9][O:8][C:7]([CH3:18])([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)[C:6]=2[CH:19]=1.[F:20][C:21]1[CH:22]=[C:23]([C:30]#[N:31])[CH:24]=[C:25](B(O)O)[CH:26]=1>>[F:20][C:21]1[CH:22]=[C:23]([CH:24]=[C:25]([C:2]2[CH:3]=[CH:4][C:5]3[NH:11][C:10](=[O:12])[CH2:9][O:8][C:7]([CH3:18])([C:13]4[S:14][CH:15]=[CH:16][CH:17]=4)[C:6]=3[CH:19]=2)[CH:26]=1)[C:30]#[N:31]

Participants

3

Reactant 2

HCID 23435605(3-Cyano-5-fluorophenyl)boronic acidHCID 688661097-Bromo-5-methyl-5-thien-2-yl-1,5-dihydro-4,1-benzoxazepin-2(3H)-one

Product 1

HCID 111648303-Fluoro-5-(5-methyl-2-oxo-5-thien-2-yl-1,2,3,5-tetrahydro-4,1-benzoxazepin-7-yl)benzonitrile

Procedure

Prepared from 7-bromo-5-methyl-5-thien-2-yl-1,5-dihydro-4,1-benzoxazepin-2(3H)-one and 5-fluoro-3-cyanobenzeneboronic acid generally according to the coupling procedure described in example 1. 1H-NMR (DMSO-d6) δ 10.18 (s, 1H), 8.09 (s, 1H), 7.96 (dt, J=9.8, 2.4 Hz, 1H), 7.80 (dt, J=8.3, 1.5 Hz, 1H), 7.76 (dd, J=8.3, 2.0 Hz, 1H), 7.72 (d, J=2.0 Hz, 1H), 7.55 (dd, J=5.4, 1.5 Hz, 1H), 7.28 (d, J=8.3 Hz, 1H), 6.99 (dd, J=4.9, 3.4 Hz, 1H), 6.89 (dd, J=3.4, 1.5 Hz, 1H), 4.17 (d, J=16.1 Hz, 1H), 4.04 (d, J=16.1 Hz, 1H), 2.12 (s, 3H); MS (ES) m/z 379 (M+H)+.

Sources & evidence

ORD record
ord-a2a45ea67d9046f3b0d0a1b5028da5c8
Source dataset
uspto-grants-2009_10
Patent number
US07598237B2

Reaction notes

Loading…