N,N'-Dimethylethylenediamine → 5-(1-phenyl-1H-1,2,3-triazol-4-yl)indolin-2-one

HRID 588270Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:8]=[N+:9]=[N-:10].[Na+].C(=O)([O-])[O-].[Na+].[Na+].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+].CNCCNC.C[Si]([C:41]#[C:42][C:43]1[CH:44]=[C:45]2[C:49](=[CH:50][CH:51]=1)[NH:48][C:47](=[O:52])[CH2:46]2)(C)C>CCO.O.[Cu]I>[C:2]1([N:8]2[CH:41]=[C:42]([C:43]3[CH:44]=[C:45]4[C:49](=[CH:50][CH:51]=3)[NH:48][C:47](=[O:52])[CH2:46]4)[N:10]=[N:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of iodobenzene (204 mg, 1 mmol), sodium azide (130 mg, 2 mmol), sodium carbonate (53 mg, 0.5 mmol), CuI (19 mg, 0.1 mmol), sodium ascorbate (20 mg) and N,N′-dimethylethylenediamine (18 ul, 0.2 mmol) in EtOH (1.5 ml) and water (0.5 ml) were added 5-((trimethylsilyl)ethynyl)indolin-2-one (115 mg, 0.5 mmol), and stirred at 80° C. for 2 h. After cooling to ambient temp, EtOH was removed under reduced pressure. The residue was suspended in EtOH and stirred for 1 h at rt and filtered. The filtrate was washed with water and hexane and dried under vacuo to give 5-(1-phenyl-1H-1,2,3-triazol-4-yl)indolin-2-one (106 mg).

Workup

temperatureAfter cooling to ambient temp
customEtOH was removed under reduced pressure
stirringstirred for 1 h at rt
filtrationfiltered
washThe filtrate was washed with water and hexane
customdried under vacuo

Sources & evidence

ORD record: ord-082e19c0c39b4f7b9eed21deada74a06
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09227962B2

Reaction notes

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