1-(4-Bromo-2-fluoro-phenyl)-6,7-difluoro-4-methoxy-5-nitro-1,3-dihydro-benzoimidazol-2-one → 5-Amino-1-(4-bromo-2-fluoro-phenyl)-6,7-difluoro-4-methoxy-1,3-dihydro-benzoimidazol-2-one

HRID 1914874Notes

Reaction equation

HRID 1914874 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3[C:13]([F:23])=[C:14]([F:22])[C:15]([N+:19]([O-])=O)=[C:16]([O:17][CH3:18])[C:11]=3[NH:10][C:9]2=[O:24])=[C:4]([F:25])[CH:3]=1>[Zn]>[NH2:19][C:15]1[C:14]([F:22])=[C:13]([F:23])[C:12]2[N:8]([C:5]3[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=3[F:25])[C:9](=[O:24])[NH:10][C:11]=2[C:16]=1[O:17][CH3:18]

Participants

3

Reactant 1

HCID 683134131-(4-Bromo-2-fluoro-phenyl)-6,7-difluoro-4-methoxy-5-nitro-1,3-dihydro-benzoimidazol-2-one

Product 1

HCID 683134025-Amino-1-(4-bromo-2-fluoro-phenyl)-6,7-difluoro-4-methoxy-1,3-dihydro-benzoimidazol-2-oneYield 95%

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

Intermediate I-12a was prepared from 1-(4-bromo-2-fluoro-phenyl)-6,7-difluoro-4-methoxy-5-nitro-1,3-dihydro-benzoimidazol-2-one (2 g, 0.00478 mol) and zinc powder (1.9 g, 0.0287 mol) using procedures analogous to those described above for the preparation of Intermediate I-11a to afford 1.7 g of the product (95% yield). H1NMR (DMSO-d6, 300 MHz): δ 11.52 (s, 114), 7.83 (dd, 1H), 7.62-7.55 (m, 2H), 4.99 (s, 2H), 3.75 (s, 3H).

Workup

  1. customthose described above for the preparation of Intermediate I-11a

Sources & evidence

ORD record
ord-101507161241455e8d6f6386b42efa65
Source dataset
uspto-grants-2013_12
Patent number
US08614239B2

Reaction notes

Loading…