HCID 178504782, compound → 2-(2,6-dichloro-4-methanesulfonylphenyl)-2H-pyrazolo[4,3-c]pyridine

HRID 626683Notes

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]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:14][C:13]=1[Cl:23])=[N+]=[N-]>C1(C)C=CC=CC=1>[Cl:23][C:13]1[CH:14]=[C:15]([S:19]([CH3:22])(=[O:21])=[O:20])[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-methanesulfonylphenyl)amine (4.21 mmol) in toluene (15 mL) was heated to 105° C. for 18 hours. The reaction mixture was allowed to cool and then concentrated under reduced pressure. The residue was recrystallised from ethyl acetate and the solid was collected by filtration to afford the title compound as a beige solid (0.75 g, 52% yield). 1H NMR (300 MHz, DMSO-d6): δ 9.38 (d, J=1.4 Hz, 1H) 9.15 (d, J=1.0 Hz, 1H), 8.34 (s, 2H) 8.31 (d, J=6.4 Hz, 1H) 7.68 (dt, J=6.4, 1.2 Hz, 1H) 3.49 (s, 3H). LCMS (Method D): RT=1.72 min, m/z: 342 [M+H+].

Workup

temperatureto cool
concentrationconcentrated under reduced pressure
customThe residue was recrystallised from ethyl acetate
filtrationthe solid was collected by filtration

Sources & evidence

ORD record: ord-821cbe6d2f6c4d0eaf8316b6c2b19e23
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309240B2

Reaction notes

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