Cesium carbonate → HCID 86685987, compound

HRID 2277703Notes

Reaction equation

HRID 2277703 reaction equation
[C@H]1(N)[CH2:6][CH2:5][CH2:4][CH2:3][C@@H:2]1[NH2:7].[C:9]([O-:12])([O-])=O.[Cs+].[Cs+].[Cl:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[C:22](=[O:26])[NH:21][CH2:20][CH2:19]2.BrC1C(C=O)=CC=NC=1>O1CCOCC1.[Cu]I.O>[Cl:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[C:22](=[O:26])[N:21]([C:3]1[CH:4]=[C:5]([CH:9]=[O:12])[CH:6]=[N:7][CH:2]=1)[CH2:20][CH2:19]2

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 4793071,2-Diaminocyclohexane, (+)-HCID 27629973-Bromopyridine-4-carboxaldehydeHCID 193756376-Chloro-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 86685987HCID 86685987, compoundYield 348.8%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

CuI (190 mg, 1 mmol), (1S,2S)-cyclohexane-1,2-diamine (228 mg, 2 mmol) and Cs2CO3 (6.5 g, 20 mmol) were added to a solution of 6-chloro-3,4-dihydro-2H-isoquinolin-1-one (1.82 g, 10 mmol, intermediate A-2) and 5-bromo-pyridine-4-carbaldehyde (3.72 g, 20 mmol) in dioxane (15 mL). The reaction mixture was heated to 150° C. using microwave for 2.5 hours before it was poured into H2O (50 mL) and extracted with EtOAc (2×20 mL). The organic layers were washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude product (2.0 g, 70%) as brown oil. MS: 287.0 (M+H+).

Workup

  1. customfor 2.5 hours
  2. extractionextracted with EtOAc (2×20 mL)
  3. washThe organic layers were washed with brine
  4. customdried over anhy
  5. filtrationNa2SO4, filtered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-58b16153334a4180bd69e23a0e1eb83c
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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