Dichloromethane → 6-[(5-Chloro-thiophen-2-yl)-hydroxy-(3-methyl-3h-imidazol-4-yl)-methyl]-4-(3-hydroxy-phenyl)-1-methyl-1h-quinolin-2-one

HRID 1384362Notes

Reaction equation

[Cl:1][C:2]1[S:6][C:5]([C:7]([OH:33])([C:27]2[N:28]([CH3:32])[CH:29]=[N:30][CH:31]=2)[C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13](=[O:18])[CH:12]=[C:11]3[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25]C)[CH:20]=2)=[CH:4][CH:3]=1.B(Br)(Br)Br.[CH2:38](Cl)Cl>>[Cl:1][C:2]1[S:6][C:5]([C:7]([OH:33])([C:27]2[N:28]([CH3:32])[CH:29]=[N:30][CH:31]=2)[C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH3:38])[C:13](=[O:18])[CH:12]=[C:11]3[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([OH:25])[CH:20]=2)=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 6344Dichloromethane

HCID 25134Boron tribromide

HCID 224654366-[(5-Chloro-thiophen-2-yl)-hydroxy-(3-methyl-3h-imidazol-4-yl)-methyl]-4-(3-methoxy-phenyl)-1h-quinolin-2-one

Product 1

HCID 224653946-[(5-Chloro-thiophen-2-yl)-hydroxy-(3-methyl-3h-imidazol-4-yl)-methyl]-4-(3-hydroxy-phenyl)-1-methyl-1h-quinolin-2-oneYield 67%

Procedure

Following the same procedure as that described in Example 34A, the title compound of example 31 (100 mg, 0.203 mmol) was treated with BBr3 in CH2Cl2 (1M, 1.02 ml, 1.02 mmol) to give the title compound (64 mg, 67% yield).

Sources & evidence

ORD record: ord-a5932720ac6e4698bae982caced219c7
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06258824B1

Reaction notes

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