Methyl iodide → HCID 131715179, compound

HRID 652450Notes

Reaction equation

HRID 652450 reaction equation
[H-].[Na+].[O:3]=[C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](=[O:13])[N:5]1[CH2:14][CH2:15][C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([CH2:25][NH:26][CH:27]=[O:28])[CH:23]=2)[NH:18][CH:17]=1.[CH3:29]I>CN(C)C=O.C(OCC)(=O)C>[OH2:3].[O:13]=[C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:4](=[O:3])[N:5]1[CH2:14][CH2:15][C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([CH2:25][NH:26][CH:27]=[O:28])[CH:23]=2)[N:18]([CH3:29])[CH:17]=1.[O:13]=[C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:4](=[O:3])[N:5]1[CH2:14][CH2:15][C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([CH2:25][NH:26][CH:27]=[O:28])[CH:23]=2)[N:18]([CH3:29])[CH:17]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 12803119HCID 12803119, compound

Product 1

HCID 131715179HCID 131715179, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride in oil (80%, 0.045 g) was added under nitrogen to a stirred solution of N-[[3-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]-1H-indol-5-yl]methyl]formamide (0.5 g) in dimethylformamide (20 ml) and stirring continued for 30 min. The solution was then treated with methyl iodide (0.2 ml). After 3 h, the solution was diluted with ethyl acetate (150 ml) washed with brine (10%, 3×50 ml), dried (sodium sulphate), filtered and evaporated to dryness giving a yellow solid which was crystallised from ethyl acetate to give the title compound (0.2 g) as an off-white solid m.p. 189°-191°.

Workup

  1. waitAfter 3 h
  2. washwashed with brine (10%, 3×50 ml)
  3. dry with materialdried (sodium sulphate)
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customgiving a yellow solid which
  7. customwas crystallised from ethyl acetate

Sources & evidence

ORD record
ord-76e51e32fe9c4fbf85f64526a8393967
Source dataset
uspto-grants-1987_06
Patent number
US04672067

Reaction notes

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