Diethylamine → HCID 67281918, compound

HRID 1616158Notes

Reaction equation

HRID 1616158 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:22]=[CH:23][CH:24]=1)[CH2:6][N:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][C:11]([C:17]([O:19][CH3:20])=[O:18])=[CH:12][CH:13]=2)[C:8]1=[O:21].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:31]([NH:33][CH2:34][CH3:35])[CH3:32]>O1CCCC1.O>[CH2:31]([N:33]([CH2:2][C:3]1[CH:4]=[C:5]([CH:22]=[CH:23][CH:24]=1)[CH2:6][N:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][C:11]([C:17]([O:19][CH3:20])=[O:18])=[CH:12][CH:13]=2)[C:8]1=[O:21])[CH2:34][CH3:35])[CH3:32]

Participants

6

Reactant 3

HCID 8021DiethylamineHCID 10796Cesium carbonateHCID 67281879HCID 67281879, compound

Product 1

HCID 67281918HCID 67281918, compoundYield 72.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-[3-(bromomethyl)benzyl]-1-oxo-1,2-dihydroisoquinoline-7-carboxylate (0.10 g, 0.26 mmol) in tetrahydrofuran (7 mL) was added cesium carbonate (0.25 g, 0.78 mmol) and diethylamine (40 μL, 0.39 mmol). The reaction mixture was stirred at rt overnight. The mixture was diluted with water and extracted with EtOAc (2×). The combined organic phases were then washed with water, and brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by flash silica gel chromatography (0% to 5% MeOH/DCM) to afford methyl 2-{3-[(diethylamino)methyl]benzyl}-1-oxo-1,2-dihydroisoquinoline-7-carboxylate (71 mg, 72%). LC-MS: (FA) ES+ 379.

Workup

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic phases were then washed with water, and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash silica gel chromatography (0% to 5% MeOH/DCM)

Sources & evidence

ORD record
ord-4ddd34a4f8cc4c00abafc588edbc0c32
Source dataset
uspto-grants-2014_07
Patent number
US08765773B2

Reaction notes

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