N,N'-Dimethylethylenediamine → HCID 90417386, compound

HRID 588268Notes

Reaction equation

HRID 588268 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.CNCCNC.[C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)#[CH:19].[N-:26]=[N+:27]=[N-:28].[Na+].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>CCO.O.[Cu]I>[C:20]1([C:18]2[N:26]=[N:27][N:28]([C:2]3[CH:3]=[C:4]4[C:8](=[CH:9][CH:10]=3)[NH:7][C:6](=[O:11])[CH2:5]4)[CH:19]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

9

Reactant 5

HCID 8070N,N'-DimethylethylenediamineHCID 10821PhenylacetyleneHCID 33557Sodium AzideHCID 6111935-Bromo-2-oxindoleHCID 23667548Sodium Ascorbate

Product 1

HCID 90417386HCID 90417386, compoundYield 65.1%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

The mixture of 5-bromoindolin-2-one (530 mg, 2.5 mmol), N,N′-dimethylethylenediamine (44 mg, 0.5 mmol), ethynylbenzene (274 μl, 2.5 mmol), CuI (48 mg, 0.25 mmol), sodium azide (325 mg, 5 mmol) and sodium ascorbate (99 mg, 0.5 mmol) in EtOH (7 ml), H2O (3 ml) was heated to 80° C. for 18 h. All reagents were re-added and heated to 80° C. for 10 h. After confirming the reaction complete, reaction mixture was cooled to room temperature and EtOH was removed under reduced pressure. 20 ml of water was added and filtered. The filtrate was washed with water and hexane and dried under vacuo to give 5-(4-phenyl-1H-1,2,3-triazol-1-yl)indolin-2-one (450 mg).

Workup

  1. additionAll reagents were re-added
  2. temperatureheated to 80° C. for 10 h
  3. customreaction mixture
  4. temperaturewas cooled to room temperature
  5. customEtOH was removed under reduced pressure
  6. addition20 ml of water was added
  7. filtrationfiltered
  8. washThe filtrate was washed with water and hexane
  9. customdried under vacuo

Sources & evidence

ORD record
ord-24697c3086c049e7ae02141995b1f45d
Source dataset
uspto-grants-2016_01
Patent number
US09227962B2

Reaction notes

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