Methyl iodide → HCID 86766954, compound

HRID 2410132Notes

Reaction equation

HRID 2410132 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:38])=[C:6]([N:8]2[C:15](=[O:16])[C:14]3[N:13]=[C:12]([C:17]4[C:18]([O:25][CH3:26])=[N:19][C:20]([O:23][CH3:24])=[N:21][CH:22]=4)[N:11]([CH:27]([CH3:29])[CH3:28])[C:10]=3[C@H:9]2[C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=2[CH3:37])[CH:7]=1.[CH3:39][Si]([N-][Si](C)(C)C)(C)C.[K+].CI>C1COCC1.CCOC(C)=O>[Cl:36][C:33]1[CH:34]=[CH:35][C:30]([C:9]2([CH3:39])[C:10]3[N:11]([CH:27]([CH3:28])[CH3:29])[C:12]([C:17]4[C:18]([O:25][CH3:26])=[N:19][C:20]([O:23][CH3:24])=[N:21][CH:22]=4)=[N:13][C:14]=3[C:15](=[O:16])[N:8]2[C:6]2[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[CH3:38])=[C:31]([CH3:37])[CH:32]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 86766904HCID 86766904, compound

Product 1

HCID 86766954HCID 86766954, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of the product from example 76 (100 mg, 0.18 mmol) in THF (2 mL) at −78° C. was added KHMDS (217 μL, 0.22 mmol, 1M in THF) and the mixture was stirred at −78° C. for 15 min. Methyl iodide (34 μL, 0.54 mmol) was added and the mixture was allowed to warm to rt and the mixture was stirred at rt for 20 h. The reaction mixture was diluted with EtOAc and extracted with a 5% citric acid solution. The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated. The residue was purified by preparative HPLC, then the residue was lyophilized in dioxane. tR: 1.25 min (LC-MS 2); ESI-MS: 566.3/568.2 [M+H]+ (LC-MS 2).

Workup

  1. temperatureto warm to rt
  2. stirringthe mixture was stirred at rt for 20 h
  3. extractionextracted with a 5% 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 by preparative HPLC

Sources & evidence

ORD record
ord-1ec95fb1232643a6bf1326fee5ed6f53
Source dataset
uspto-grants-2014_08
Patent number
US08815926B2

Reaction notes

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