Cesium carbonate → tert-Butyl 1-(1-((2-chloro-6-methylpyridin-4-yl)methyl)-1H-imidazol-2-yl)-2-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)ethylcarbamate

HRID 2099826Notes

Reaction equation

HRID 2099826 reaction equation
[C:1]([O:5][C:6](=[O:33])[NH:7][CH:8]([C:28]1[NH:29][CH:30]=[CH:31][N:32]=1)[CH2:9][C:10]1[CH:18]=[C:17]([CH3:19])[C:16]2[C:12](=[CH:13][N:14]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[N:15]=2)[CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:34][C:35]1[CH:40]=[C:39]([CH2:41]Cl)[CH:38]=[C:37]([CH3:43])[N:36]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[Cl:34][C:35]1[CH:40]=[C:39]([CH2:41][N:32]2[CH:31]=[CH:30][N:29]=[C:28]2[CH:8]([NH:7][C:6](=[O:33])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:9][C:10]2[CH:18]=[C:17]([CH3:19])[C:16]3[C:12](=[CH:13][N:14]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:25])([CH3:27])[CH3:26])[N:15]=3)[CH:11]=2)[CH:38]=[C:37]([CH3:43])[N:36]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 216981672-Chloro-4-(chloromethyl)-6-methylpyridineHCID 57794668tert-Butyl-1-(1H-imidazol-2-yl)-2-(7-methyl-2-[{2-[trimethylsilyl]ethoxy}methyl]-2H-indazol-5-yl)ethylcarbamate

Product 1

HCID 57794619tert-Butyl 1-(1-((2-chloro-6-methylpyridin-4-yl)methyl)-1H-imidazol-2-yl)-2-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)ethylcarbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-Butyl-1-(1H-imidazol-2-yl)-2-(7-methyl-2-[{2-[trimethylsilyl]ethoxy}methyl]-2H-indazol-5-yl)ethylcarbamate (0.1 g, 0.212 mmol), 2-chloro-4-(chloromethyl)-6-methylpyridine (39.0 mg, 0.222 mmol, 1.05 equiv), and cesium carbonate (0.21 g, 0.64 mmol) were combined in dimethylformamide (2.0 mL). After stirring at room temperature for 16 h, the solvents were removed and the residue purified by column chromatography to afford 0.1 g (77%). Mass spec.: 611.21 (MH)+.

Workup

  1. customthe solvents were removed
  2. customthe residue purified by column chromatography
  3. customto afford 0.1 g (77%)

Sources & evidence

ORD record
ord-e3f201f8d5514f7ebef75b755a0d0313
Source dataset
uspto-grants-2009_08
Patent number
US07569578B2

Reaction notes

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