Methyl iodide → Methyl 2-[5-cyano-2-methyl-4-(trifluoromethyl)-1H-indol-1-yl]-2-methylpropanoate

HRID 913530Notes

Reaction equation

HRID 913530 reaction equation
[C:1]([C:3]1[C:4]([C:19]([F:22])([F:21])[F:20])=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH:12]([CH3:17])[C:13]([O:15][CH3:16])=[O:14])[C:7]([CH3:18])=[CH:6]2)#[N:2].IC.[CH3:25]C([O-])(C)C.[K+]>C1COCC1>[C:1]([C:3]1[C:4]([C:19]([F:22])([F:21])[F:20])=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]([CH3:25])([CH3:17])[C:13]([O:15][CH3:16])=[O:14])[C:7]([CH3:18])=[CH:6]2)#[N:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 57800182Methyl 2-[5-cyano-2-methyl-4-(trifluoromethyl)-1H-indol-1-yl]propanoate

Product 1

HCID 57800496Methyl 2-[5-cyano-2-methyl-4-(trifluoromethyl)-1H-indol-1-yl]-2-methylpropanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-[5-cyano-2-methyl-4-(trifluoromethyl)-1H-indol-1-yl]propanoate (0.065 g, 0.209 mmol) in THF (1 mL) was added iodomethane (0.59 g, 4.18 mmol), followed by dropwise addition of t-BuOK (1M in THF, 0.63 mL, 6.3 mmol). After 10 min, the mixture was partitioned between EtOAc and 0.1N HCl. The organic phase was washed with sat'd brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography (0-25% EtOAc-hexanes gradient) to afford the title compound: MS (ES) m/z 325 (M+1).

Workup

  1. customthe mixture was partitioned between EtOAc and 0.1N HCl
  2. washThe organic phase was washed with sat'd brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (0-25% EtOAc-hexanes gradient)

Sources & evidence

ORD record
ord-f418c2691ef24c5d82ac4da4ae5fa52f
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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