HCID 178514520, compound → 2-(2,6-Dichloro-4-nitrophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine

HRID 626764Notes

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:18]([Cl:19])=[CH:17][C:16]([N+:20]([O-:22])=[O:21])=[CH:15][C:14]=1[Cl:23])=[N+]=[N-]>C1(C)C=CC=CC=1>[Cl:23][C:14]1[CH:15]=[C:16]([N+:20]([O-:22])=[O:21])[CH:17]=[C:18]([Cl:19])[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

Participants

Conditions

Temperature: 105 °C

Procedure

A suspension of [1-(4-azido-5-fluoropyridin-3-yl)-meth-(E)-ylidene]-(2,6-dichloro-4-nitrophenyl)-amine (5.89 g, 16.6 mmol) in toluene (80 mL) was heated at 105° C. 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 (0-5% methanol in DCM) to afford the title compound (4.78 g, 81% yield). 1H NMR (300 MHz, CDCl3): δ 9.13 (d, J=2.2 Hz, 1H), 8.43 (s, 2H), 8.39 (d, J=2.4 Hz, 1H), 8.26 (d, J=3.4 Hz, 1H).

Workup

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

Sources & evidence

ORD record: ord-3759d056b63b47f38c81f7f8d3ce2772
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309240B2

Reaction notes

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