Water → HCID 57423968, compound

HRID 1875327Notes

Reaction equation

HRID 1875327 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C@H:6]([CH3:13])[CH2:5]2.[H-].[Na+].[CH3:16]I.O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH3:16])[C@H:6]([CH3:13])[CH2:5]2

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57423967HCID 57423967, compound

Product 1

HCID 57423968HCID 57423968, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

426 mg (1.7 mmol) (R)-6-bromo-3-methyl-3,4-dihydro-2H-isoquinolin-1-one are dissolved in 3 ml DMF and at 0° C. combined with 80 mg (2 mmol) sodium hydride (60% in mineral oildispersion). After 10 minutes 122 μl (1.9 mmol) methyl iodide are added dropwise, and the mixture is stirred for 16 hours at RT. Then the reaction mixture is mixed with water and extracted three times with ethyl acetate. The combined organic phases are dried on sodium sulphate, filtered and evaporated down i. vac. The residue is purified by flash chromatography on silica gel (eluant DCM/MeOH 20:1).

Workup

  1. extractionextracted three times with ethyl acetate
  2. customThe combined organic phases are dried on sodium sulphate
  3. filtrationfiltered
  4. customevaporated down i
  5. customThe residue is purified by flash chromatography on silica gel (eluant DCM/MeOH 20:1)

Sources & evidence

ORD record
ord-17c7ffa907814c2c807a8cd571f6f917
Source dataset
uspto-grants-2012_11
Patent number
US08309542B2

Reaction notes

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