HCID 178514519, compound → 2-(2,6-dichloro-4-fluorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine

HRID 626742Notes

Reaction equation

HRID 626742 reaction equation
[N:1]([C:4]1[C:9]([F:10])=[CH:8][N:7]=[CH:6][C:5]=1/[CH:11]=[N:12]/[C:13]1[C:18]([Cl:19])=[CH:17][C:16]([F:20])=[CH:15][C:14]=1[Cl:21])=[N+]=[N-]>C1(C)C=CC=CC=1>[Cl:21][C:14]1[CH:15]=[C:16]([F:20])[CH:17]=[C:18]([Cl:19])[C:13]=1[N:12]1[CH:11]=[C:5]2[CH:6]=[N:7][CH:8]=[C:9]([F:10])[C:4]2=[N:1]1

Participants

3

Reactant 1

HCID 178514519HCID 178514519, compound

Product 1

HCID 696717192-(2,6-dichloro-4-fluorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridineYield 77%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of [1-(4-azido-5-fluoropyridin-3-yl)-meth-(E)-ylidene]-(2,6-dichloro-4-fluorophenyl)-amine (14.7 mmol) in toluene (40 mL) was heated under reflux for 16 hours then allowed to cool to room temperature. The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (0-50% ethyl acetate in cyclohexane) to afford the title compound as an off-white solid (3.38 g, 77% yield). LCMS (Method D): RT=2.84 min, m/z: 300 [M+H+].

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customThe residue was purified by silica gel flash chromatography (0-50% ethyl acetate in cyclohexane)

Sources & evidence

ORD record
ord-acec05edc0a04d8fb28f51abed48e466
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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