N,N'-Dimethylethylenediamine → HCID 86685957, compound

HRID 2277665Notes

Reaction equation

HRID 2277665 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[Cl:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15](=[O:19])[NH:14][CH2:13][CH2:12]2.C(=O)([O-])[O-].[K+].[K+].CNCCNC>O1CCOCC1.[Cu]I>[Cl:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15](=[O:19])[N:14]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)[CH2:13][CH2:12]2

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 122863-BromopyridineHCID 193756376-Chloro-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 86685957HCID 86685957, compoundYield 65.3%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

In a sealed tube, 3-bromopyridine (0.1 g, 0.633 mmol) was combined with 6-chloro-3,4-dihydroisoquinolin-1(2H)-one (intermediate A-2) (0.115 g, 633 mmol), copper (I) iodide (0.012 g, 0.063 mmol), potassium carbonate (0.175 g, 1.27 mmol) and N,N′-dimethylethylenediamine (0.013 g, 0.127 mmol) in 1,4-dioxane (2 mL). The reaction mixture was heated at 110° C. overnight. The mixture was cooled to room temperature, filtered through dicalite and washed with DCM. The residue was purified by silica gel flash chromatography eluting with a 5 to 100% EtOAc-heptane gradient to give the title compound (0.107 g, 65%) as a white solid. MS: 259.1 (M+H+).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered through dicalite
  3. washwashed with DCM
  4. customThe residue was purified by silica gel flash chromatography
  5. washeluting with a 5 to 100% EtOAc-heptane gradient

Sources & evidence

ORD record
ord-7ca1c58e630644b5b72005aa55c1ae38
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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