Cesium carbonate → 4-(5-Methyl-pyridin-2-yl)-1-phenyl-1H-indazole-6-carboxylic acid methyl ester

HRID 59811Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[N:10][NH:11]2)=[C:7]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][N:15]=2)[CH:6]=1)=[O:4].I[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CN[C@H]1CCCC[C@@H]1NC.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.[Cu]I>[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[N:10][N:11]2[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:7]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][N:15]=2)[CH:6]=1)=[O:4]

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 4-(5-methyl-pyridin-2-yl)-1H-indazole-6-carboxylic acid methyl ester (0.183 g, 0.684 mmol) in DMF (5 mL) was added iodobenzene (0.15 g, 0.753 mmol), CuI (0.028 g, 0.137 mmol), (1S,2S)—N,N′-dimethylcyclohexane-1,2-diamine (0.04 g, 0.274 mmol), and Cs2CO3 (0.15 g, 1.36 mmol). The reaction mixture was stirred at 110° C. overnight, then cooled to room temperature and partitioned between water and ethyl acetate. The organic layer was separated, dried over MgSO4, filtered and concentrated under reduced pressure. Purification of the residue by column chromatography gave 0.12 g (53%) of 4-(5-Methyl-pyridin-2-yl)-1-phenyl-1H-indazole-6-carboxylic acid methyl ester.

Workup

temperaturecooled to room temperature
custompartitioned between water and ethyl acetate
customThe organic layer was separated
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customPurification of the residue by column chromatography

Sources & evidence

ORD record: ord-4b99091bc42d43fdb7266c35cddf836f
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440956B2

Reaction notes

Loading…