HCID 178509759, compound → 3-Chloro-2-(7-fluoropyrazolo[4,3-c]pyridin-2-yl)-benzonitrile

HRID 626754Notes

Reaction equation

HRID 626754 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][CH:18]=[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]=[CH:18][CH:19]=1)[C:15]#[N:16]

Participants

3

Reactant 1

HCID 178509759HCID 178509759, compound

Product 1

HCID 696715363-Chloro-2-(7-fluoropyrazolo[4,3-c]pyridin-2-yl)-benzonitrileYield 55%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-{[1-(4-azido-5-fluoropyridin-3-yl)-meth-(E)-ylidene]-amino}-3-chlorobenzonitrile (5.16 g, 17.2 mmol) in toluene (60 mL) was heated at 105° C. for 5 hours. The resultant mixture was cooled 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 beige solid (2.57 g, 55% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.42 (d, J=2.6 Hz, 1H), 9.26 (d, J=2.5 Hz, 1H), 8.33 (d, J=3.8 Hz, 1H), 8.24-8.19 (m, 2H), 7.92 (t, J=8.1 Hz, 1H).

Workup

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

Sources & evidence

ORD record
ord-71397315a65b4df888e5f1beb3b634ce
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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