Methyl iodide → HCID 117778654, compound

HRID 1527067Notes

Reaction equation

HRID 1527067 reaction equation
[OH:1][CH:2]([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[CH3:26]>C1COCC1.C(OCC)(=O)C>[CH3:26][O:1][CH:2]([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]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 117778794HCID 117778794, compound

Product 1

HCID 117778654HCID 117778654, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of tert-butyl 1-(3-hydroxybutan-2-yl)-2-methyl-1H-indole-3-carboxylate (500 mg, 1.65 mmol) in THF (8 mL) was added sodium hydride (330 mg, 8.25 mmol) at 30° C. under N2. The reaction was stirred for 20 min. Then iodomethane (0.4 mL) was added and the reaction was stirred at 60° C. for 3 hrs. Then the mixture was diluted with ethyl acetate, washed with water and saturated aqueous NaHCO3. The crude product was purified by column chromatography on silica gel eluted with petroleum ether:ethyl acetate=80:1 to afford the title compound as a yellow solid which was used directly (400 mg, 76.8%).

Workup

  1. stirringthe reaction was stirred at 60° C. for 3 hrs
  2. washwashed with water and saturated aqueous NaHCO3
  3. customThe crude product was purified by column chromatography on silica gel
  4. washeluted with petroleum ether

Sources & evidence

ORD record
ord-1512d09e4b15406ab90662a537ac9956
Source dataset
uspto-grants-2015_07
Patent number
US09085583B2

Reaction notes

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