Potassium Carbonate → (+/-)-tert-Butyl 2-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)-1-(1-(2-nitrophenyl)-1H-imidazol-2-yl)ethylcarbamate

HRID 2099798Notes

Reaction equation

HRID 2099798 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].F[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[N+:41]([O-:43])=[O:42].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[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]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[N+:41]([O-:43])=[O:42])[CH:30]=[CH:31][N:32]=2)[CH:18]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 738951-Fluoro-2-nitrobenzeneHCID 57794668tert-Butyl-1-(1H-imidazol-2-yl)-2-(7-methyl-2-[{2-[trimethylsilyl]ethoxy}methyl]-2H-indazol-5-yl)ethylcarbamate

Product 1

HCID 57794697(+/-)-tert-Butyl 2-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)-1-(1-(2-nitrophenyl)-1H-imidazol-2-yl)ethylcarbamate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
125 °C

Procedure

tert-Butyl-1-(1H-imidazol-2-yl)-2-(7-methyl-2-[{2-[trimethylsilyl]ethoxy}methyl]-2H-indazol-5-yl)ethylcarbamate (25 mg, 0.53 mmol), 1-fluoro-2-nitrobenzene (14 mg, 0.13 mmol), and potassium carbonate (18.2 mg, 0.13 mmol) were combined in acetonitrile (1.0 mL) and heated via microwave at 125° C. for 30 h. The reaction was concentrated, dissolved in methylene chloride, and washed with water (2×), brine (2×), dried over sodium sulfate, and concentrated. Purification by column chromatography afforded 20.4 mg (65%).

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutiondissolved in methylene chloride
  3. washwashed with water (2×), brine (2×)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customPurification by column chromatography
  7. customafforded 20.4 mg (65%)

Sources & evidence

ORD record
ord-63c1ae77b23143d591e1e3b9c6a0ddc2
Source dataset
uspto-grants-2009_08
Patent number
US07569578B2

Reaction notes

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