HCID 178509786, compound → 3-Fluoro-2-(7-fluoropyrazolo[4,3-c]pyridin-2-yl)-benzonitrile

HRID 626788Notes

Reaction equation

HRID 626788 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]([F:21])=[CH:19][CH:18]=[CH:17][C:14]=1[C:15]#[N:16])=[N+]=[N-]>C1(C)C=CC=CC=1>[F: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 178509786HCID 178509786, compound

Product 1

HCID 696719503-Fluoro-2-(7-fluoropyrazolo[4,3-c]pyridin-2-yl)-benzonitrileYield 86.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-{[1-(4-azido-5-fluoropyridin-3-yl)meth-(E)-ylidene]amino}-3-fluorobenzonitrile (5.19 g, 18.2 mmol) in toluene (90 mL) was heated under reflux for 4 hours. The resultant mixture was cooled to room temperature and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (50-100% ethyl acetate in cyclohexane) to afford the title compound as a beige solid (4.02 g, 86% yield). LCMS (Method C): RT=2.41 min, m/z: 257 [M+H+].

Workup

  1. temperatureunder reflux for 4 hours
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by silica gel flash chromatography (50-100% ethyl acetate in cyclohexane)

Sources & evidence

ORD record
ord-72d46d16d34a4b749355b8407fbe235f
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

Loading…