Methyl iodide → HCID 58986357, compound

HRID 420812Notes

Reaction equation

HRID 420812 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=2)[C:10]([C:18]([O:20][CH3:21])=[O:19])=[C:9]1[CH:22]([CH3:24])[CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CI.[C:27]([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:27])=[CH:14][CH:15]=2)[C:10]([C:18]([O:20][CH3:21])=[O:19])=[C:9]1[CH:22]([CH3:24])[CH3:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 58986341HCID 58986341, compound2×

Product 1

HCID 58986357HCID 58986357, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 1-benzyl-5-hydroxy-2-isopropyl-1H-indole-3-carboxylate (Compound 32, 560 mg, 1.73 mmol) in DMF (6.0 ml) was added methyl iodide (0.32 ml, 5.20 mmol) and K2CO3 (718 mg, 5.20 mmol). The mixture was stirred at room temperature for 16 h, diluted with EtOAc, washed with H2O, brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with 0-20% EtOAc-hexanes to yield methyl 1-benzyl-2-isopropyl-5-methoxy-1H-indole-3-carboxylate (Compound 33) as a yellow solid.

Workup

  1. washwashed with H2O, brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography on silica gel eluting with 0-20% EtOAc-hexanes

Sources & evidence

ORD record
ord-32dd4fd4b34b414fa69e55c404063aef
Source dataset
uspto-grants-2012_01
Patent number
US08097644B2

Reaction notes

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