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 1936308Notes

Reaction equation

HRID 1936308 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])[CH2:12][CH: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

4

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 22465457HCID 22465457, compound

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-2f9940dcb07e4c9cbfd784b06c99ab14
Source dataset
uspto-grants-2002_05
Patent number
US06388092B2

Reaction notes

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