Methyl iodide → HCID 82490717, compound

HRID 1475452Notes

Reaction equation

HRID 1475452 reaction equation
[Li][CH2:2]CCC.[Cl:6][C:7]1[CH:15]=[C:14]2[C:10]([CH2:11][C:12](=[O:16])[NH:13]2)=[CH:9][CH:8]=1.CN(CCN(C)C)C.CI>C1COCC1>[Cl:6][C:7]1[CH:15]=[C:14]2[C:10]([CH:11]([CH3:2])[C:12](=[O:16])[NH:13]2)=[CH:9][CH:8]=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

Conditions

Temperature
-20 °C

Procedure

BuLi (2.2 M in cyclohexane, 22 mL, 48 mmol) was added dropwise at −78° C. to a solution of 6-chloro-1,3-dihydro-indol-2-one (4 g, 24 mmol) and TMEDA (11.2 mL, 79 mmol) in THF (100 mL) under N2. The solution was stirred for 30 minutes at the same temperature and then MeI (2.2 mL, 36 mmol) was added. The reaction mixture was warmed to −20° C. and stirred at this temperature for 1.5 h. The reaction was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The organic phase was dried over MgSO4, filtered and concentrated in vacuo. Chromatography gave the title compound (2.7 g) as a pale pink solid. MS: [M+H]+=182.

Workup

  1. stirringstirred at this temperature 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 over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e3f3c835fa2b4f5ca78d226bb5a9b12e
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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