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

HRID 1816910Notes

Reaction equation

HRID 1816910 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]([CH2:18][CH3:19])([C:13]3[CH:17]=[CH:16][S:15][CH:14]=3)[C:6]=2[CH:20]=1.[C:21]([C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[C:27]([F:29])[CH:28]=1)#[N:22]>>[CH2:18]([C:7]1([C:13]2[CH:17]=[CH:16][S:15][CH:14]=2)[C:6]2[CH:20]=[C:2]([C:25]3[CH:24]=[C:23]([CH:28]=[C:27]([F:29])[CH:26]=3)[C:21]#[N:22])[CH:3]=[CH:4][C:5]=2[NH:11][C:10](=[O:12])[CH2:9][O:8]1)[CH3:19]

Participants

3

Reactant 2

HCID 23435605(3-Cyano-5-fluorophenyl)boronic acidHCID 688658237-bromo-5-ethyl-5-thien-3-yl-1,5-dihydro-4,1-benzoxazepin-2(3H)-one

Product 1

HCID 112463303-(5-Ethyl-2-oxo-5-thien-3-yl-1,2,3,5-tetrahydro-4,1-benzoxazepin-7-yl)-5-fluorobenzonitrile

Procedure

Prepared from 7-bromo-5-ethyl-5-thien-3-yl-1,5-dihydro-4,1-benzoxazepin-2(3H)-one and 3-cyano-5-fluorobenzeneboronic acid using the coupling procedure described in example 1. 1H-NMR (DMSO-d6) δ 10.07 (s, 1H), 8.07 (t, J=1.5 Hz, 1H), 7.94 (dt, J=10.3, 2.0 Hz, 1H), 7.80 (m, 1H), 7.73 (dd, J=8.3, 2.0 Hz, 1H), 7.63 (d, J=2.4 Hz, 1H), 7.57 (dd, J=4.9, 2.9 Hz, 1H), 7.27 (m, 2H), 7.17 (dd, J=4.9, 1.5 Hz, 1H), 4.02 (d, J=15.6 Hz, 1H), 3.96 (d, J=15.6 Hz, 1H), 2.54 (m, 1H), 2.49 (m, 1H), 0.74 (t, J=7.3 Hz, 3H); MS (ES) m/z 393 (M+H)+.

Sources & evidence

ORD record
ord-bb98015dbae74290af06f91c45aca1bd
Source dataset
uspto-grants-2009_10
Patent number
US07598237B2

Reaction notes

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