HCID 178514513, compound → 2-(2-chloro-6-fluorophenyl)-2H-pyrazolo[4,3-c]pyridine

HRID 626674Notes

Reaction equation

HRID 626674 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]([F: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]([F: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

3

Reactant 1

HCID 178514513HCID 178514513, compound

Product 1

HCID 696716312-(2-chloro-6-fluorophenyl)-2H-pyrazolo[4,3-c]pyridineYield 54.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of [1-(4-azidopyridin-3-yl)meth-(E)-ylidene]-(2-chloro-6-fluorophenyl)amine (17 mmol) in toluene (50 mL) was heated at 105° C. for 18 hours. The reaction mixture was cooled and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (60-70% ethyl acetate in cyclohexane) to afford the title compound as a yellow solid (2.29 g, 54% yield). 1H NMR (400 MHz, CDCl3): δ 9.31 (d, J=1.5 Hz, 1H), 8.38-8.33 (m, 2H), 7.65 (dd, J=6.4, 1.4 Hz, 1H), 7.52 (td, J=8.3, 5.6 Hz, 1H), 7.45-7.41 (m, 1H), 7.30-7.24 (m, 1H). LCMS (Method C): RT=1.42, m/z: 248 [M+H+].

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by silica gel flash chromatography (60-70% ethyl acetate in cyclohexane)

Sources & evidence

ORD record
ord-0d21518e7f1e4ab48692945b409c57f2
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

Loading…