Methyl iodide → HCID 21887961, compound

HRID 719784Notes

Reaction equation

HRID 719784 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].CI.[NH:9]1[C:17]2[C:12](=[CH:13][C:14]([C:18](=[O:41])[CH2:19][CH2:20][CH2:21][CH2:22][N:23]([CH2:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[O:39][CH3:40])[C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:15][CH:16]=2)[CH2:11][CH2:10]1>CN(C)C=O>[CH3:1][N:9]1[C:17]2[C:12](=[CH:13][C:14]([C:18](=[O:41])[CH2:19][CH2:20][CH2:21][CH2:22][N:23]([CH2:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[O:39][CH3:40])[C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:15][CH:16]=2)[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 21886799HCID 21886799, compound

Product 1

HCID 21887961HCID 21887961, compoundYield 33.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

Potassium carbonate (166 mg) and methyl iodide (170 mg) were added to a solution of tert-butyl 5-(2,3-dihydro-1H-indol-5-yl)-5-oxopentyl[2-(2-methoxyphenyl)ethyl]carbamate (362 mg) obtained in Reference Example 50 in dimethylformamide (2 ml), and the mixture was stirred at 60 to 70° C. for 5 hours. The solvent was evaporated under reduced pressure, water was added to the resulting residue, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel chromatography (eluting solvent; hexane:ethyl acetate=1:1) to give the title compound as a pale yellow oil (125 mg).

Workup

  1. customThe solvent was evaporated under reduced pressure, water
  2. additionwas added to the resulting residue
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe resulting residue was purified by silica gel chromatography (eluting solvent; hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-659f87c9a661403982e9cb75a87a8bc8
Source dataset
uspto-grants-2006_11
Patent number
US07132547B2

Reaction notes

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