Methyl iodide → HCID 82490717, compound

HRID 1475394Notes

Reaction equation

HRID 1475394 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[CH3:12]N(CCN(C)C)C.[Li]CCCC.IC>C1COCC1>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]([CH3:12])[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 7363446-Chloro-1,3-dihydroindol-2-oneHCID 178418339Butyllithium

Product 1

HCID 82490717HCID 82490717, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (−78° C.) solution of 6-chloro-1,3-dihydro-indol-2-one (4.0 g, 24 mmol) and TMEDA (11.2 mL, 79 mmol) in THF (100 mL) was slowly added BuLi (2.2 M solution in cyclohexane, 22 mL, 48 mmol). The solution was stirred for 30 minutes at the same temperature and then iodomethane (2.2 mL, 36 mmol) was slowly added. The reaction was stirred at −20° C. for 1.5 h. The reaction was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The organic phase was dried (MgSO4), filtered and concentrated in vacuo. Chromatography (SiO2, EtOAc/Petrol 2:8) gave the title compound (2.7 g) as a pale pink solid. MS: [M+H]+=182.

Workup

  1. stirringThe reaction was stirred at −20° C. for 1.5 h
  2. customThe reaction was quenched with saturated aqueous NH4Cl
  3. extractionextracted with EtOAc
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-99bc449dab2b42c3ba0fe5caa7826e03
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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