5-Bromo-2-fluorobenzonitrile → 5-(5,5-Dimethyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-7-yl)-2-fluorobenzonitrile

HRID 1816918Notes

Reaction equation

HRID 1816918 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]([CH3:14])([CH3:13])[C:6]=2[CH:15]=1.Br[C:17]1[CH:18]=[CH:19][C:20]([F:25])=[C:21]([CH:24]=1)[C:22]#[N:23]>>[CH3:13][C:7]1([CH3:14])[C:6]2[CH:15]=[C:2]([C:17]3[CH:18]=[CH:19][C:20]([F:25])=[C:21]([CH:24]=3)[C:22]#[N:23])[CH:3]=[CH:4][C:5]=2[NH:11][C:10](=[O:12])[CH2:9][O:8]1

Participants

3

Reactant 2

HCID 27249005-Bromo-2-fluorobenzonitrileHCID 688658147-bromo-5,5-dimethyl-1,5-dihydro-4,1-benzoxazepin-2(3H)-one

Product 1

HCID 249570985-(5,5-Dimethyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-7-yl)-2-fluorobenzonitrile

Procedure

Prepared from 7-bromo-5,5-dimethyl-1,5-dihydro-4,1-benzoxazepin-2(3H)-one and 5-bromo-2-fluorobenzonitrile generally according to the coupling procedure described in examples 82 and 1. 1H-NMR (DMSO-d6) δ 10.02 (s, 1H), 8.32 (dd, J=6.3, 2.4 Hz, 1H), 8.11 (m, 1H), 7.62 (m, 1H), 7.58 (m, 2H), 7.19 (d, J=8.8 Hz, 1H), 4.26 (s, 2H), 1.62 (s, 6H); MS (ES) m/z 311 (M+H)+.

Sources & evidence

ORD record
ord-0d95572e1f2e4504a68c2187ed1bfa6a
Source dataset
uspto-grants-2009_10
Patent number
US07598237B2

Reaction notes

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