Sodium Methoxide → 6-[2-Ethyl-5-fluoro-4-(2-trimethylsilanyl-ethoxymethoxy)-phenyl]-1-(tetrahydro-pyran-2-yl)-1H-indazole-3-carboximidic acid methyl ester

HRID 340061Notes

Reaction equation

HRID 340061 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([O:9][CH2:10][O:11][CH2:12][CH2:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[C:6]([F:18])=[CH:5][C:4]=1[C:19]1[CH:27]=[C:26]2[C:22]([C:23]([C:34]#[N:35])=[N:24][N:25]2[CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][O:29]2)=[CH:21][CH:20]=1)[CH3:2].[CH3:36][O-:37].[Na+]>CO>[CH3:36][O:37][C:34]([C:23]1[C:22]2[C:26](=[CH:27][C:19]([C:4]3[CH:5]=[C:6]([F:18])[C:7]([O:9][CH2:10][O:11][CH2:12][CH2:13][Si:14]([CH3:17])([CH3:15])[CH3:16])=[CH:8][C:3]=3[CH2:1][CH3:2])=[CH:20][CH:21]=2)[N:25]([CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][O:29]2)[N:24]=1)=[NH:35]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 866762696-[2-Ethyl-5-fluoro-4-(2-trimethylsilanyl-ethoxymethoxy)-phenyl]-1-(tetrahydro-pyran-2-yl)-1H-indazole-3-carbonitrile

Product 1

HCID 866762716-[2-Ethyl-5-fluoro-4-(2-trimethylsilanyl-ethoxymethoxy)-phenyl]-1-(tetrahydro-pyran-2-yl)-1H-indazole-3-carboximidic acid methyl esterYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-[2-ethyl-5-fluoro-4-(2-trimethylsilanyl-ethoxymethoxy)-phenyl]-1-(tetrahydro-pyran-2-yl)-1H-indazole-3-carbonitrile (Preparation 6, 37.42 g, 75.6 mmol) in methanol (700 mL) was added sodium methoxide (12.21 g, 226.8 mmol) and the reaction mixture was then stirred at room temperature for 18 hours. The solvent was removed in vacuo and the residue was partitioned between EtOAc (1 L) and water (500 mL). The organic layer was washed with water (500 mL), dried over MgSO4 and concentrated in vacuo to give the title compound as a gum (37.26 g) in a 94% yield.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between EtOAc (1 L) and water (500 mL)
  3. washThe organic layer was washed with water (500 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-adc603e9faa744c596fcace5e66a97bf
Source dataset
uspto-grants-2014_11
Patent number
US08895544B2

Reaction notes

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