HCID 178509963, compound → 3,5-Dichloro-4-pyrazolo[4,3-c]pyridine-2-ylbenzonitrile

HRID 626688Notes

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:19]([Cl:20])=[CH:18][C:15]([C:16]#[N:17])=[CH:14][C:13]=1[Cl:21])=[N+]=[N-]>C1(C)C=CC=CC=1>[Cl:21][C:13]1[CH:14]=[C:15]([CH:18]=[C:19]([Cl:20])[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)[C:16]#[N:17]

Participants

Conditions

Temperature: 105 °C

Procedure

A mixture of 4-{[1-(4-azidopyridin-3-yl)meth-(E)-ylidene]amino}-3,5-dichlorobenzonitrile (21.4 mmol) in toluene (80 mL) was heated to 105° C. for 1 hour. The reaction mixture was cooled and concentrated under reduced pressure. The resultant residue was purified by silica gel flash chromatography (0-100% ethyl acetate in cyclohexane) to afford the title compound as a yellow solid (4.10 g, 66% yield). 1H NMR (300 MHz, CDCl3): δ 9.36 (d, J=1.4 Hz, 1H), 8.39 (d, J=6.5 Hz, 1H), 8.35 (d, J=1.0 Hz, 1H), 7.85 (s, 2H), 7.68-7.66 (m, 1H). LCMS (Method D): RT=1.66 min, m/z: 289 [M+H+].

Workup

temperatureThe reaction mixture was cooled
concentrationconcentrated under reduced pressure
customThe resultant residue was purified by silica gel flash chromatography (0-100% ethyl acetate in cyclohexane)

Sources & evidence

ORD record: ord-4037d18cca0441cfbd620d418c94b90e
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309240B2

Reaction notes

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