Methyl iodide → HCID 67272220, compound

HRID 250251Notes

Reaction equation

HRID 250251 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]([C:8]1[C:16]2[C:11](=[CH:12][C:13]([Br:18])=[C:14]([OH:17])[CH:15]=2)[N:10]([CH:19]2[CH2:21][CH2:20]2)[C:9]=1[CH3:22])=[O:7])[CH3:4].[CH3:23]I>CN(C=O)C.O.CCOCC>[CH2:3]([O:5][C:6]([C:8]1[C:16]2[C:11](=[CH:12][C:13]([Br:18])=[C:14]([O:17][CH3:23])[CH:15]=2)[N:10]([CH:19]2[CH2:20][CH2:21]2)[C:9]=1[CH3:22])=[O:7])[CH3:4]

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67271637HCID 67271637, compound

Product 1

HCID 67272220HCID 67272220, compoundYield 88.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% in mineral oil, 71 mg, 1.8 mmol) is added to a solution of 6-bromo-1-cyclopropyl-5-hydroxy-2-methyl-1H-indole-3-carboxylic acid ethyl ester (200 mg, 0.590 mmol) in DMF (4.0 mL). The mixture is stirred for 20 minutes at room temperature. Methyl iodide (110 μL, 1.77 mmol) is added and the mixture is stirred for 1 h at room temperature. The mixture is diluted with water and ether. The layers are separated. The ether layer is washed with water and brine, dried over MgSO4, and concentrated under reduced pressure. The residue is triturated in ethyl acetate-hexane to give the title compound as an off-white solid (183 mg, 88%). ES/MS m/e 353.8 (M+1).

Workup

  1. stirringthe mixture is stirred for 1 h at room temperature
  2. customThe layers are separated
  3. washThe ether layer is washed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is triturated in ethyl acetate-hexane

Sources & evidence

ORD record
ord-91bac89da30e4ac787919930c5a55dc3
Source dataset
uspto-grants-2011_01
Patent number
US07863302B2

Reaction notes

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