Methyl iodide → HCID 89740593, compound

HRID 2206578Notes

Reaction equation

HRID 2206578 reaction equation
[OH:1][C:2]([CH3:23])([CH3:22])[CH:3]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[C:6]1[CH3:21])[CH3:4].[H-].[Na+].I[CH3:27]>C1COCC1>[CH3:27][O:1][C:2]([CH3:22])([CH3:23])[CH:3]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[C:6]1[CH3:21])[CH3:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 89740020HCID 89740020, compound

Product 1

HCID 89740593HCID 89740593, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of (±)-tert-butyl 1-(3-hydroxy-3-methylbutan-2-yl)-2-methyl-1H-indole-3-carboxylate (0.2594 g, 0.817 mmol) and THF (8 mL), in a 50 mL round bottom flask, cooled to 0° C. was added sodium hydride (0.065 g, 1.634 mmol). The reaction was then heated at 45° C. for 2 h then iodomethane (0.102 ml, 1.634 mmol) was added and the reaction was heated at that temperature overnight. The reaction was quenched with 1N HCl and brine, extracted with EtOAc, dried over Na2SO4, filtered, concentrated, deposited onto silica gel with aid of DCM, and purified by column chromatography using 5% EtOAc in Hex as eluent to provide (±)-tert-butyl 1-(3-methoxy-3-methylbutan-2-yl)-2-methyl-1H-indole-3-carboxylate (257.8 mg, 95%). LRMS (M+H+) m/z: calcd 332.45. found 332.2.

Workup

  1. temperaturethe reaction was heated at that temperature overnight
  2. customThe reaction was quenched with 1N HCl and brine
  3. extractionextracted with EtOAc
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-98ac91b83e2d49aea65a92bf0e416163
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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