HCID 178510122, compound → 3-Chloro-5-fluoro-2-(7-fluoropyrazolo[4,3-c]pyridin-2-yl)-benzonitrile

HRID 626782Notes

Reaction equation

HRID 626782 reaction equation
[N:1]([C:4]1[C:9]([F:10])=[CH:8][N:7]=[CH:6][C:5]=1/[CH:11]=[N:12]/[C:13]1[C:20]([Cl:21])=[CH:19][C:18]([F:22])=[CH:17][C:14]=1[C:15]#[N:16])=[N+]=[N-]>C1(C)C=CC=CC=1>[Cl:21][C:20]1[C:13]([N:12]2[CH:11]=[C:5]3[CH:6]=[N:7][CH:8]=[C:9]([F:10])[C:4]3=[N:1]2)=[C:14]([CH:17]=[C:18]([F:22])[CH:19]=1)[C:15]#[N:16]

Participants

3

Reactant 1

HCID 178510122HCID 178510122, compound

Product 1

HCID 696715683-Chloro-5-fluoro-2-(7-fluoropyrazolo[4,3-c]pyridin-2-yl)-benzonitrileYield 93%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-{[1-(4-azido-5-fluoropyridin-3-yl)-meth-(E)-ylidene]-amino}-3-chloro-5-fluorobenzonitrile (1.67 g, 5.25 mmol) in anhydrous toluene (25 mL) was heated under reflux for 4.5 hours. The resultant mixture was allowed to cool to room temperature and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (0-5% methanol in DCM) to afford the title compound as a yellow solid (1.41 g, 93% yield). LCMS (Method C): RT=2.71 min, m/z: 291 [M+H+].

Workup

  1. temperatureunder reflux for 4.5 hours
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by silica gel flash chromatography (0-5% methanol in DCM)

Sources & evidence

ORD record
ord-514e778e05a64fccaa7634d7029e9b2d
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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