Water → HCID 66547999, compound

HRID 1467931Notes

Reaction equation

HRID 1467931 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([OH:13])[N:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[N:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:27](Cl)(=[O:29])[CH3:28].O>C(Cl)(Cl)Cl>[C:27]([O:13][C:11]1[N:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[N:9]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)[CH:12]=1)(=[O:29])[CH3:28]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 178515505HCID 178515505, compound

Product 1

HCID 66547999HCID 66547999, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3-(4-bromophenyl)-1-(pyridin-2-yl)-1H-pyrazol-5-ol (3 mmol, 1 equivalent) was dissolved in 10 mL of CHCl3 and 1.2 equivalents of triethylamine were added thereto at 0° C. Then, 1 equivalent of acetyl chloride was added thereto, followed by refluxing for 10 minutes. After the reaction was completed, H2O (10 mL) was added to the solution which was then extracted with CHCl3. The organic layer was dried over anhydrous MgSO4, filtered, concentrated, and then separated by column chromatography (n-hexane:EA=5:1 (v/v)) to afford the title compound.

Workup

  1. customat 0° C
  2. temperatureby refluxing for 10 minutes
  3. extractionwas then extracted with CHCl3
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customseparated by column chromatography (n-hexane:EA=5:1 (v/v))

Sources & evidence

ORD record
ord-378e2b56c6be4b11bd03078c069a62f1
Source dataset
uspto-grants-2015_04
Patent number
US09000176B2

Reaction notes

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