2-(2,6-Dichloro-4-nitrophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine → 3-Chloro-2-(7-fluoro-pyrazolo[4,3-c]pyridin-2-yl)-5-nitrobenzonitrile

HRID 626771Notes

Reaction equation

HRID 626771 reaction equation
ClC1C=C([N+]([O-])=O)C=C(Cl)C=1N1C=C2C=NC=C(F)C2=N1.[N:22]([C:25]1[C:30]([F:31])=[CH:29][N:28]=[CH:27][C:26]=1/[CH:32]=[N:33]/[C:34]1[C:41]([Cl:42])=[CH:40][C:39]([N+:43]([O-:45])=[O:44])=[CH:38][C:35]=1[C:36]#[N:37])=[N+]=[N-]>>[Cl:42][C:41]1[C:34]([N:33]2[CH:32]=[C:26]3[CH:27]=[N:28][CH:29]=[C:30]([F:31])[C:25]3=[N:22]2)=[C:35]([CH:38]=[C:39]([N+:43]([O-:45])=[O:44])[CH:40]=1)[C:36]#[N:37]

Participants

3

Reactant 2

HCID 696718262-(2,6-Dichloro-4-nitrophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridineHCID 178510232HCID 178510232, compound

Product 1

HCID 696710793-Chloro-2-(7-fluoro-pyrazolo[4,3-c]pyridin-2-yl)-5-nitrobenzonitrileYield 58%

Conditions

Temperature
107 °C

Procedure

Following the procedure described for 2-(2,6-dichloro-4-nitrophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine, 2-{[1-(4-azido-5-fluoropyridin-3-yl)-meth-(E)-ylidene]-amino}-3-chloro-5-nitrobenzonitrile was heated at 107° C. for 3.5 hours. After purification by silica gel chromatography (0-5% methanol in DCM), the product was triturated 5 times with diethyl ether/cyclohexane (1:1) to afford the title compound as a yellow solid (3.31 g, 58% yield). LCMS (Method C): RT=2.89 min, m/z: 318 [M+H+].

Workup

  1. customAfter purification by silica gel chromatography (0-5% methanol in DCM)
  2. customthe product was triturated 5 times with diethyl ether/cyclohexane (1:1)

Sources & evidence

ORD record
ord-e62bc1e809ab4c76858c8c4d81742dd0
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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