2-Chloro-4-cyanopyridine → HCID 18677150, compound

HRID 1634084Notes

Reaction equation

HRID 1634084 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]([F:16])([F:15])[F:14])=[CH:11][C:10]([C:17]([F:20])([F:19])[F:18])=[N:9]2)=[CH:4][CH:3]=1.Cl[C:22]1[CH:27]=[C:26]([C:28]#[N:29])[CH:25]=[CH:24][N:23]=1>O1CCOCC1.C(OCC)(=O)C>[C:28]([C:26]1[CH:25]=[CH:24][N:23]=[C:22]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([N:8]3[C:12]([C:13]([F:14])([F:15])[F:16])=[CH:11][C:10]([C:17]([F:20])([F:19])[F:18])=[N:9]3)=[CH:6][CH:7]=2)[CH:27]=1)#[N:29]

Participants

5

Reactant 2

HCID 5686382-Chloro-4-cyanopyridineHCID 27406684-(3,5-Bis(trifluoromethyl)-1H-pyrazol-1-yl)aniline

Product 1

HCID 18677150HCID 18677150, compoundYield 54.8%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 1-(4′-aminophenyl)-3,5-bis(trifluoromethyl)pyrazole (0.36 g) and 2-chloro-4-cyanopyridine (0.14 g) in dioxane (1 mL) was heated at 125° C. in a sealed tube for 5 days. The mixture was diluted with ethyl acetate and washed with water. The organic phase was dried, filtered and evaporated. Chromatography of the residue over silica gel (methylene chloride to 2% ethanol/methylene chloride gradient gave the above-named compound (0.22 g) mp 152-153° C. NMR (CDCl3) 8.45 (1H, m), 7.86 (3H, m), 7.48 (2H, d), 7.20 (1H, br s), 7.07 (1H, s), 6.91 (1H, m).

Workup

  1. washwashed with water
  2. customThe organic phase was dried
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-75206f775d2343318e1bbd2630cf48e5
Source dataset
uspto-grants-2003_01
Patent number
US06506747B1

Reaction notes

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