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

HRID 1914876Notes

Reaction equation

HRID 1914876 reaction equation
[NH2:1][C:2]1[C:19]([F:20])=[C:18]([F:21])[C:5]2[N:6]([C:10]3[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][C:11]=3[F:17])[C:7](=[O:9])[NH:8][C:4]=2[C:3]=1[O:22]C.C(Cl)Cl>>[NH2:1][C:2]1[C:19]([F:20])=[C:18]([F:21])[C:5]2[N:6]([C:10]3[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][C:11]=3[F:17])[C:7](=[O:9])[NH:8][C:4]=2[C:3]=1[OH:22]

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 683134025-Amino-1-(4-bromo-2-fluoro-phenyl)-6,7-difluoro-4-methoxy-1,3-dihydro-benzoimidazol-2-one

Product 1

HCID 683137725-Amino-1-(4-bromo-2-fluoro-phenyl)-6,7-difluoro-4-hydroxy-1,3-dihydro-benzoimidazol-2-oneYield 88%

Procedure

Intermediate I-14a was prepared from 5-amino-1-(4-bromo-2-fluoro-phenyl)-6,7-difluoro-4-methoxy-1,3-dihydro-benzoimidazol-2-one (I-12a: 1.7 g, 0.00438 mol) and borontribromide using procedures analogous to those used for the preparation of Intermediate I-13a in DCM (10.9 mL, 0.0109 mol) to afford 850 mg of the product (88% yield).

Sources & evidence

ORD record
ord-71c327e3ffaf493f9ae5ebc7fccffb99
Source dataset
uspto-grants-2013_12
Patent number
US08614239B2

Reaction notes

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