HCID 178509437, compound → HCID 69671939, compound

HRID 626809Notes

Reaction equation

HRID 626809 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:20]([Cl:21])=[CH:19][C:18]([Br:22])=[CH:17][C:14]=1[C:15]#[N:16])=[N+]=[N-]>C1(C)C=CC=CC=1>[Br:22][C:18]1[CH:19]=[C:20]([Cl:21])[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]([CH:17]=1)[C:15]#[N:16]

Participants

3

Reactant 1

HCID 178509437HCID 178509437, compound

Product 1

HCID 69671939HCID 69671939, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-{[1-(4-azido-5-fluoropyridin-3-yl)meth-(E)-ylidene]amino}-5-bromo-3-chlorobenzonitrile (˜22.6 mmol) in toluene (100 mL) was heated under reflux for 5 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 (4.61 g, 58% yield over two steps). 1H NMR (400 MHz, DMSO-d6): δ 9.37 (d, J=2.7 Hz, 1H), 9.27 (d, J=2.6 Hz, 1H), 8.61-8.58 (m, 2H), 8.34 (d, J=3.8 Hz, 1H).

Workup

  1. temperatureunder reflux for 5 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-38592f8b6df94fc6a4e4c616958a5c1b
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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