Methyl iodide → HCID 69036273, compound

HRID 2415443Notes

Reaction equation

HRID 2415443 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[CH:5]([N:7]1[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[CH:13]=2)[C:8]1=[O:26])[CH3:6])[CH3:2].[CH3:28][Si]([N-][Si](C)(C)C)(C)C.[K+].CI.[Cl-].[NH4+]>C1COCC1>[CH2:1]([O:3][C:4](=[O:27])[C:5]([N:7]1[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH2:18][C:19]3[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=3)[CH:13]=2)[C:8]1=[O:26])([CH3:28])[CH3:6])[CH3:2]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 69035867HCID 69035867, compound

Product 1

HCID 69036273HCID 69036273, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

The 2-[6-(4-fluoro-benzyloxy)-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl]-propionic acid ethyl ester (Example 10b, 365 mg, 0.983 mmol) was solved in THF (3.5 ml) and at −78° C. was added potassium bis(trimethylsilyl)amide (7.8 mL, 3.9 mmol), followed 15 min later by methyl iodide (0.368 mL, 5.89 mmol). The reaction mixture was stirred at −78° C. for 5 hours. Ammonium chloride was added and the reaction extracted with dichloromethane. The organic phases were dried over sodium sulfate and evaporated. The crude product was purified by column chromatography (hexane to hexane/ethyl acetate 1:1) to give 288 mg (76%) of the product. MS: m/e=386.2 (M+H+).

Workup

  1. extractionthe reaction extracted with dichloromethane
  2. dry with materialThe organic phases were dried over sodium sulfate
  3. customevaporated
  4. customThe crude product was purified by column chromatography (hexane to hexane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-131df637f26c4bd08cc7ecaf4c5da021
Source dataset
uspto-grants-2004_11
Patent number
US06818774B2

Reaction notes

Loading…