Cesium carbonate → HCID 86760645, compound

HRID 902177Notes

Reaction equation

HRID 902177 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][N:9]=[C:8]2[CH:14]=[O:15])=[O:4].Br[CH2:17][C:18]1[CH:22]=[C:21]([C:23]2[S:24][C:25]([Cl:28])=[CH:26][CH:27]=2)[O:20][N:19]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:17][C:18]1[CH:22]=[C:21]([C:23]3[S:24][C:25]([Cl:28])=[CH:26][CH:27]=3)[O:20][N:19]=1)[N:9]=[C:8]2[CH:14]=[O:15])=[O:4]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 111501463-Bromomethyl-5-(5-chloro-thiophen-2-yl)-isoxazoleHCID 178497393HCID 178497393, compound

Product 1

HCID 86760645HCID 86760645, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 200 mg 3-Formyl-1H-indazole-5-carboxylic acid methyl ester in 4 mL DMF, 273 mg 3-Bromomethyl-5-(5-chloro-thiophen-2-yl)-isoxazole [prepared by adopting a procedure described by Ewing, William R.; Becker, Michael R.; Choi-Sledeski, Yong Mi; Pauls, Heinz W.; He, Wei; Condon, Stephen M.; Davis, Roderick S.; Hanney, Barbara A.; Spada, Alfred P.; Burns, Christopher J.; Jiang, John Z.; Li, Aiwen; Myers, Michael R.; Lau, Wan F.; Poli, Gregory B; PCT Int. Appl. (2001) 460 pp. WO 0107436 A2] and 320 mg Cs2CO3 were added and the mixture was stirred at room temperature for 1.5 h. This crude reaction mixture was subjected to the subsequent oxidation step.

Workup

  1. customThis crude reaction mixture

Sources & evidence

ORD record
ord-65ccefb546d64cdfbb36eb413be9212e
Source dataset
uspto-grants-2008_04
Patent number
US07365088B2

Reaction notes

Loading…