HCID 178514518, compound → 2-(4-Bromo-2,6-dichlorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine

HRID 626801Notes

Reaction equation

HRID 626801 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]([Br:20])=[CH:15][C:14]=1[Cl:21])=[N+]=[N-]>C1(C)C=CC=CC=1>[Br:20][C:16]1[CH:17]=[C:18]([Cl:19])[C:13]([N:12]2[CH:11]=[C:5]3[CH:6]=[N:7][CH:8]=[C:9]([F:10])[C:4]3=[N:1]2)=[C:14]([Cl:21])[CH:15]=1

Participants

3

Reactant 1

HCID 178514518HCID 178514518, compound

Product 1

HCID 696717852-(4-Bromo-2,6-dichlorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridineYield 67%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of [1-(4-azido-5-fluoropyridin-3-yl)meth-(E)-ylidene]-(4-bromo-2,6-dichlorophenyl)amine (˜60 mmol) in toluene (200 mL) was heated at 105° C. for 2 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 (14.5 g, 67% yield over two steps). 1H NMR (400 MHz, DMSO-d6): δ 9.25 (d, J=2.7 Hz, 1H), 9.20 (d, J=2.6 Hz, 1H), 8.28 (dd, J=3.8, 0.5 Hz, 1H), 8.19 (s, 2H).

Workup

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

Sources & evidence

ORD record
ord-9997b47a75ec42a0bffd133255ac0633
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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