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 50174Notes

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 mmol0 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-034c97ca203e42caad32e8623d4bcc73
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06710209B2

Reaction notes

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