Diketene → HCID 86068758, compound

HRID 734728Notes

Reaction equation

HRID 734728 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[F:7][C:8]1[CH:16]=[C:15]2[C:11]([CH:12]=[N:13][NH:14]2)=[CH:10][C:9]=1[NH2:17]>C(#N)C.C(OCC)C.S([O-])([O-])(=O)=O.[Cu+2]>[F:7][C:8]1[CH:16]=[C:15]2[C:11]([CH:12]=[N:13][NH:14]2)=[CH:10][C:9]=1[NH:17][C:4](=[O:5])[CH2:3][C:2](=[O:6])[CH3:1]

Participants

6

Reactant 2

HCID 12661DiketeneHCID 450905046-fluoro-1H-indazol-5-amine

Product 1

HCID 86068758HCID 86068758, compound

Reagents, catalysts & solvents 3

HCID 24462Copper SulfateCatalystHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

Diketene (stabilized w/copper sulfate, 1.0 mL, 12.9 mmol, 1.5 equiv) was added to a suspension of 6-fluoro-1H-indazol-5-amine (1.3 g, 8.6 mmol, 1 equiv) in acetonitrile (8 mL) at 0° C. over 30 minutes. The reaction mixture was then stirred at room temperature for 16 hours. The mixture was diluted with cold diethyl ether (20 mL) and the solid product was collected by filtration and washed several times with cold diethyl ether. The title compound was isolated as a pale brown powder (1.49 g, 74%). MS m/z 236 [M+H]+

Workup

  1. filtrationthe solid product was collected by filtration
  2. washwashed several times with cold diethyl ether

Sources & evidence

ORD record
ord-2983887ef14a424785a359a724734877
Source dataset
uspto-grants-2009_09
Patent number
US07592357B2

Reaction notes

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