HCID 178509965, compound → 3,5-Dichloro-4-(7-fluoro-pyrazolo[4,3-c]pyridin-2-yl)-benzonitrile

HRID 626719Notes

Reaction equation

HRID 626719 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:16]([C:17]#[N:18])=[CH:15][C:14]=1[Cl:22])=[N+]=[N-]>C1(C)C=CC=CC=1>[Cl:22][C:14]1[CH:15]=[C:16]([CH:19]=[C:20]([Cl:21])[C:13]=1[N:12]1[CH:11]=[C:5]2[CH:6]=[N:7][CH:8]=[C:9]([F:10])[C:4]2=[N:1]1)[C:17]#[N:18]

Participants

3

Reactant 1

HCID 178509965HCID 178509965, compound

Product 1

HCID 696716113,5-Dichloro-4-(7-fluoro-pyrazolo[4,3-c]pyridin-2-yl)-benzonitrileYield 75.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 4-{[1-(4-azido-5-fluoro-pyridin-3-yl)-meth-(E)-ylidene]-amino}-3,5-dichlorobenzonitrile (4.0 g, 12.0 mmol) in toluene (50 mL) was heated under reflux for 1 hour and then cooled to room temperature. The precipitated solid was removed by filtration and washed sequentially with toluene, ethyl acetate, and 1:1 ethyl acetate:DCM. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel flash chromatography (0-100% ethyl acetate in cyclohexane) to afford the title compound as an off-white solid (2.77 g, 75% yield). 1H NMR (300 MHz, CDCl3): δ 9.11 (d, J=2.2 Hz, 1H), 8.36 (d, J=2.4 Hz, 1H), 8.24 (d, J=3.4 Hz, 1H), 7.85 (s, 2H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. customThe precipitated solid was removed by filtration
  4. washwashed sequentially with toluene, ethyl acetate, and 1:1 ethyl acetate
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by silica gel flash chromatography (0-100% ethyl acetate in cyclohexane)

Sources & evidence

ORD record
ord-c10443036b5944c98e7222bd54771f29
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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