Methyl iodide → HCID 117599820, compound

HRID 513226Notes

Reaction equation

HRID 513226 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:6]([CH3:12])[CH:5]2[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH3:19][Si]([N-][Si](C)(C)C)(C)C.[K+].IC>O1CCCC1.CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:6]([CH3:12])[C:5]2([CH3:19])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 117599742HCID 117599742, compound

Product 1

HCID 117599820HCID 117599820, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-30 °C

Procedure

To a solution of 5-Bromo-2-methyl-3-phenyl-2,3-dihydro-isoindol-1-one (250 mg; 0.83 mmol) in 2.5 ml of anhydrous tetrahydrofuran at −30° C. is added an 0.5 mol/l potassium bis(trimethylsilyl)amide (2.5 ml; 1.24 mmol) solution. After 30 minutes iodomethane (77 μl; 1.24 mmol) is added and stirred for 16 hours at −30° C. The reaction mixture is diluted with methanol and purified via reversed phase chromatography under basic conditions.

Workup

  1. custompurified via reversed phase chromatography under basic conditions

Sources & evidence

ORD record
ord-51ff53fb861b4ce2b1fe3b872135781e
Source dataset
uspto-grants-2015_08
Patent number
US09102684B2

Reaction notes

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