5-Bromofuran-2-carbonitrile → 5-(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)-furan-2-carbonitrile

HRID 413174

Reaction equation

HRID 413174 reaction equation
Br[C:2]1[O:3][C:4]([C:7]#[N:8])=[CH:5][CH:6]=1.[CH3:9][C:10]1([CH3:24])[C:15]2[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][C:14]=2[NH:13][C:12](=[O:23])[O:11]1>>[CH3:9][C:10]1([CH3:24])[O:11][C:12](=[O:23])[NH:13][C:14]2[CH:19]=[CH:18][C:17]([C:2]3[O:3][C:4]([C:7]#[N:8])=[CH:5][CH:6]=3)=[CH:16][C:15]1=2

Participants

3

Reactant 2

HCID 7086705-Bromofuran-2-carbonitrileHCID 10987806(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)boronic acid

Product 1

HCID 99652245-(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)-furan-2-carbonitrile

Procedure

The title compound was prepared according to the procedure B from 2-bromo-5-cyanofuran (1.0 g, 5.6 mmol) (J. Med. Chem. (1997), 40(23), 3804-3819) and (1,4-dihydro-4,4-dimethyl-2-oxo-2H-3,1-benzoxazin-6-yl)boronic acid (1.8 g, 8.18 mmol) as a white solid (0.39 g, 1.45 mmol, 17%): mp. 257-260° C.; 1H-NMR (DMSO-d6) □10.48 (s, 1H), 7.73-7.70 (m, 3H), 7.19 (d, 1H, J=3.8 Hz), 6.98 (d, 1H, J=8.9 Hz), 1.66 (s, 6H); MS ((+)−APCI) m/z=269 (M+H)+.

Sources & evidence

ORD record
ord-46a2eb52694b46ff98be170331321f06
Source dataset
uspto-grants-2003_05
Patent number
US06566358B2

Linked notes

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