HCID 178514521, compound → 2-(2-Chloro-6-fluorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine

HRID 626793Notes

Reaction equation

HRID 626793 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]([F:19])=[CH:17][CH:16]=[CH:15][C:14]=1[Cl:20])=[N+]=[N-]>C1(C)C=CC=CC=1>[Cl:20][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]([F: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 178514521HCID 178514521, compound

Product 1

HCID 696713422-(2-Chloro-6-fluorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridineYield 63%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of [1-(4-azido-5-fluoropyridin-3-yl)meth-(E)-ylidene]-(2-chloro-6-fluorophenyl)amine (˜60 mmol) in toluene (250 mL) was heated under reflux for 3 hours. The resultant mixture was cooled to room temperature and concentrated under reduced pressure. The residue was triturated with diethyl ether and the solid obtained was collected by filtration and dried to afford the title compound as an off-white solid (9.96 g, 63% yield over two steps). 1H NMR (400 MHz, DMSO-d6): δ 9.32 (d, J=2.7 Hz, 1H), 9.20 (d, J=2.6 Hz, 1H), 8.29 (d, J=3.8 Hz, 1H), 7.81-7.74 (m, 1H), 7.72-7.60 (m, 2H).

Workup

  1. temperatureunder reflux for 3 hours
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was triturated with diethyl ether
  4. customthe solid obtained
  5. filtrationwas collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-ee493f2d548c4eaebc73a26b653f5715
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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