Cesium carbonate → HCID 86686024, compound

HRID 2277729Notes

Reaction equation

HRID 2277729 reaction equation
Br[C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][C:7]3([O:16][CH2:15][C:14]([CH3:18])([CH3:17])[CH2:13][O:12]3)[C:6]=2[CH:5]=[N:4][CH:3]=1.[Cl:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[C:25](=[O:29])[NH:24][CH2:23]2.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.O.[Cu]I>[Cl:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[C:25](=[O:29])[N:24]([C:2]1[C:11]3[CH2:10][CH2:9][CH2:8][C:7]4([O:16][CH2:15][C:14]([CH3:18])([CH3:17])[CH2:13][O:12]4)[C:6]=3[CH:5]=[N:4][CH:3]=1)[CH2:23]2

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 197881085-Chloro-2,3-dihydro-1H-isoindol-1-oneHCID 86686023HCID 86686023, compound

Product 1

HCID 86686024HCID 86686024, compoundYield 86.2%

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

A mixture of 4′-bromo-5,5-dimethyl-6′,7′-dihydro-5′H-spiro[1,3-dioxane-2,8′-isoquinoline](5.0 g, 16 mmol), 5-chloro-2,3-dihydro-isoindol-1-one (2.7 g, 16 mmol), (+)-(1S,1S)-1,2-diaminocyclohexane (0.576 mL, 4.8 mmol), copper (I) iodide (456 mg, 2.4 mmol) and Cs2CO3 (10.4 g, 32 mmol) in dioxane (80 mL) was heated at 150° C. for 4 hours. After cooling to room temperature, it was diluted with water (50 mL) and extracted with EtOAc (200 mL×2). The combined organic layers were dried over anhy. Na2SO4, filtered and concentrated in vacuo to afford a crude product (5.5 g, 86%) as light yellow solid. MS: 399.1 (M+H+).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with EtOAc (200 mL×2)
  3. customThe combined organic layers were dried over anhy
  4. filtrationNa2SO4, filtered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3af573f4cfc54b49a24dccb1f095aeb2
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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