HCID 178514511, compound → 2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine

HRID 626657Notes

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][CH:15]=[CH:14][C:13]=1[Cl:19])=[N+]=[N-]>C1(C)C=CC=CC=1>[Cl:19][C:13]1[CH:14]=[CH:15][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-dichlorophenyl)amine (7.2 mmol) in toluene (20 mL) was heated to 105° C. for 18 hours. The reaction mixture was cooled and concentrated under reduced pressure. The resultant residue was purified by silica gel flash chromatography (0-70% ethyl acetate in cyclohexane) to afford the title compound as a yellow solid (1.30 g, 68% yield). 1H NMR (300 MHz, CDCl3): δ 9.31 (d, J=1.4 Hz, 1H), 8.36 (d, J=6.4 Hz, 1H), 8.30 (d, J=1.0 Hz, 1H), 7.65 (dt, J=6.4, 1.2 Hz, 1H), 7.54-7.52 (m, 2H), 7.46 (dd, J=9.5, 6.4 Hz, 1H). LCMS (Method D): RT=3.46 min, m/z: 264 [M+H+].

Workup

temperatureThe reaction mixture was cooled
concentrationconcentrated under reduced pressure
customThe resultant residue was purified by silica gel flash chromatography (0-70% ethyl acetate in cyclohexane)

Sources & evidence

ORD record: ord-1f157838291840809dac88b2603448ba
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309240B2

Reaction notes

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