Methyl iodide → HCID 86703196, compound

HRID 2204388Notes

Reaction equation

HRID 2204388 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([CH3:45])=[C:16]([N:18]2[C:25](=[O:26])[C:24]3[CH:23]=[C:22]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[O:33][CH3:34])[N:21]([CH:35]([CH3:37])[CH3:36])[C:20]=3[CH:19]2[C:38]2[CH:43]=[CH:42][C:41]([Cl:44])=[CH:40][CH:39]=2)[CH:17]=1.[CH3:46]I>C1COCC1.CCOC(C)=O>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([CH3:45])=[C:16]([N:18]2[C:25](=[O:26])[C:24]3[CH:23]=[C:22]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[O:33][CH3:34])[N:21]([CH:35]([CH3:37])[CH3:36])[C:20]=3[C:19]2([C:38]2[CH:39]=[CH:40][C:41]([Cl:44])=[CH:42][CH:43]=2)[CH3:46])[CH:17]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 72206099HCID 72206099, compound

Product 1

HCID 86703196HCID 86703196, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

KHMDS (1M/THF) (0.237) was added to a solution of 5-(5-chloro-2-methyl-phenyl)-6-(4-chloro-phenyl)-1-isopropyl-2-(2-methoxy-phenyl)-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one (Example 9) (0.198 mmol) in THF (2 mL) at −78° C. and the mixture was stirred at −78° C. for 15 min. Methyl iodide (0.594 mmol) was added and the mixture was allowed to warm to rt. After 2.5 h, the reaction mixture was diluted with EtOAc and washed with a 5% aqueous citric acid solution. The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated. The residue was purified using a RediSep® silica gel column to afford the title compound as a white solid. tR: 1.49 min (HPLC 3); ESI-MS: tR=1.43 min, [M]+ 519/521/523 (LC-MS 1); TLC: Rf=0.41 (1:1 EtOAc/heptanes).

Workup

  1. temperatureto warm to rt
  2. waitAfter 2.5 h
  3. washwashed with a 5% aqueous citric acid solution
  4. washThe organic layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified

Sources & evidence

ORD record
ord-0be3a0affa034ab68d9435c199bea2f0
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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