HCID 178514512, compound → 2-(2,6-dichloro-4-fluorophenyl)-2H-pyrazolo[4,3-c]pyridine

HRID 626700Notes

Reaction equation

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

Participants

Conditions

Temperature: 105 °C

Procedure

A mixture of [1-(4-azidopyridin-3-yl)meth-(E)-ylidene]-(2,6-dichloro-4-fluorophenyl)amine (2.09 g, 6.75 mmol) in toluene (20 mL) was heated to 105° C. for 45 minutes. The reaction was cooled 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 yellow solid (1.60 g, 84% yield). 1H NMR (300 MHz, CDCl3): δ 9.38 (s, 1H), 8.45-8.30 (m, 2H), 7.70 (d, J=6.5 Hz, 1H), 7.32 (d, J=7.7 Hz, 2H).

Workup

temperatureThe reaction was cooled
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel flash chromatography (50-100% ethyl acetate in cyclohexane)

Sources & evidence

ORD record: ord-3c1d8c49400741bfb6e25eb3a5341fd7
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309240B2

Reaction notes

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