Cesium carbonate → HCID 178432944, compound

HRID 1671307Notes

Reaction equation

HRID 1671307 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[N:4]([C:8]2[C:12]([CH3:13])=[N:11][NH:10][C:9]=2[OH:14])[N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH:22]([CH3:33])[C:23]([C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=1[Cl:32])=[O:24]>CN(C=O)C>[Cl:32][C:26]1[CH:27]=[C:28]([Cl:31])[CH:29]=[CH:30][C:25]=1[C:23](=[O:24])[CH:22]([O:14][C:9]1[NH:10][N:11]=[C:12]([CH3:13])[C:8]=1[N:4]1[C:5]([CH3:7])=[N:6][C:2]([CH3:1])=[N:3]1)[CH3:33]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 109239912-Bromo-1-(2,4-dichlorophenyl)propan-1-oneHCID 178432945HCID 178432945, compound

Product 1

HCID 178432944HCID 178432944, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

To a stirring solution of 4-(3,5-dimethyl-[1,2,4]triazol-1-yl)-5-methyl-2H-pyrazol-3-ol (Intermediate KF) (97 mg, 0.502 mmol) and cesium carbonate (164 mg, 0.502 mmol) in DMF (1.158 ml) at 50° C. is added 2-bromo-1-(2,4-dichloro-phenyl)-propan-1-one (Intermediate AA) (142 mg, 0.502 mmol) in DMF (0.772 ml). The reaction mixture is stirred under N2 at 50° C. for 1.5 hours and then left to stand @ RT overnight. The resulting suspension is filtered and the filtrate is concentrated in vacuo. Purification by trituration from EtOAc affords the title product; MS: m/z 394.0 [M+H]+

Workup

  1. waitleft
  2. waitto stand @ RT overnight
  3. filtrationThe resulting suspension is filtered
  4. concentrationthe filtrate is concentrated in vacuo
  5. customPurification by trituration from EtOAc

Sources & evidence

ORD record
ord-313068d54a194c768ecfd5306c97849a
Source dataset
uspto-grants-2011_08
Patent number
US07994203B2

Reaction notes

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