Methyl iodide → HCID 23559703, compound

HRID 705946Notes

Reaction equation

HRID 705946 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13].[H-].[Na+].[CH3:18]I>CN(C=O)C>[CH3:18][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 12770688HCID 12770688, compound

Product 1

HCID 23559703HCID 23559703, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 3-(1H-indol-2-yl)propanoate (800 mg, 3.94 mmol) in dry DMF (10 mL) was added NaH (300 mg, 7.50 mmol) at 0° C. After 15 min, MeI (0.40 mL, 6.40 mmol) was added dropwise. The mixture was stirred at room temperature for 1 h. The reaction was quenched with water (50 mL) and extracted with EA (50 mL×3). The combined organic phase was dried over sodium sulfate, filtered, and concentrated. Purification via flash chromatography then afforded the title compound (332 mg, 1.299 mmol, 85% purity, 33% yield). LCMS: rt=3.17 min, [M+H+]=218.

Workup

  1. customThe reaction was quenched with water (50 mL)
  2. extractionextracted with EA (50 mL×3)
  3. dry with materialThe combined organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification via flash chromatography

Sources & evidence

ORD record
ord-7adde262ba234e189ffa20a3622d3db2
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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