Methyl iodide → HCID 70980248, compound

HRID 1475456Notes

Reaction equation

HRID 1475456 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([Br:19])[CH:17]=2)[C:12]([CH2:21][OH:22])([CH3:20])[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH3:23]I>CN(C=O)C>[C:3]([O:7][C:8]([N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([Br:19])[CH:17]=2)[C:12]([CH2:21][O:22][CH3:23])([CH3:20])[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58221859HCID 58221859, compound

Product 1

HCID 70980248HCID 70980248, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (60% dispersion in mineral oil, 60 mg, 1.5 mmol) was added to a solution of 6-bromo-3-hydroxymethyl-3-methyl-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester (360 mg, 1.05 mmol) in dry DMF (5 mL). After 10 minutes MeI (66 μL, 1.1 mmol) was added and the stirring was maintained for 2 h. The reaction was quenched with water and extracted with EtOAc. The organic phase was dried over MgSO4 and concentrated in vacuo. Chromatography (20% EtOAc in 40-60 petroleum ether) gave the title compound (300 mg) as a colourless liquid. MS: [M−tBu]+=300.

Workup

  1. temperaturethe stirring was maintained for 2 h
  2. customThe reaction was quenched with water
  3. extractionextracted with EtOAc
  4. dry with materialThe organic phase was dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-acf088939b58487a9b4b3b87f0738cea
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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