Cesium carbonate → tert-Butyl 2-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)-1-(1-(pyridin-2-ylmethyl)-1H-imidazol-2-yl)ethylcarbamate

HRID 2099822Notes

Reaction equation

HRID 2099822 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[CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH3:19][C:17]1[C:16]2[C:12](=[CH:13][N:14]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:25])([CH3:27])[CH3:26])[N:15]=2)[CH:11]=[C:10]([CH2:9][CH:8]([NH:7][C:6](=[O:33])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[C:28]2[N:29]([CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=3)[CH:30]=[CH:31][N:32]=2)[CH:18]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 23393Picolyl chlorideHCID 57794668tert-Butyl-1-(1H-imidazol-2-yl)-2-(7-methyl-2-[{2-[trimethylsilyl]ethoxy}methyl]-2H-indazol-5-yl)ethylcarbamate

Product 1

HCID 57794714tert-Butyl 2-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)-1-(1-(pyridin-2-ylmethyl)-1H-imidazol-2-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 (35.0 mg, 0.074 mmol), 2-(chloromethyl)pyridine (13.3 mg, 0.082 mmol, 1.05 equiv), and cesium carbonate (72.3 mg, 0.22 mmol) were combined in dimethylformamide (1.5 mL). After stirring at room temperature for 16 h, the solvents were removed and the residue purified by column chromatography to afford 35.2 mg (77%). Mass spec.: 563.3 (MH)+.

Workup

  1. customthe solvents were removed
  2. customthe residue purified by column chromatography
  3. customto afford 35.2 mg (77%)

Sources & evidence

ORD record
ord-ee986aaf27484c368e2726f35d8d861d
Source dataset
uspto-grants-2009_08
Patent number
US07569578B2

Reaction notes

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