Cesium carbonate → HCID 86646900, compound

HRID 1946377Notes

Reaction equation

HRID 1946377 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:3]=1[C:4]([NH:6][C:7]1[CH:11]=[CH:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][C:14]=2[C:20]([F:23])([F:22])[F:21])[N:8]=1)=[O:5].[C:29](=[O:32])([O-])[O-:30].[Cs+].[Cs+].Br.Br[CH2:37][C:38]1[CH:43]=[CH:42][N:41]=[CH:40][CH:39]=1>CS(C)=O>[F:21][C:20]([F:23])([F:22])[C:29]([OH:30])=[O:32].[F:28][C:24]1[CH:25]=[CH:26][CH:27]=[C:2]([F:1])[C:3]=1[C:4]([NH:6][C:7]1[CH:11]=[CH:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:37][C:38]3[CH:43]=[CH:42][N:41]=[CH:40][CH:39]=3)=[CH:15][C:14]=2[C:20]([F:23])([F:21])[F:22])[N:8]=1)=[O:5]

Participants

5

Reactant 3

HCID 10796Cesium carbonate2×HCID 127522194-(Bromomethyl)pyridine hbr2×HCID 59547990HCID 59547990, compound

Product 1

HCID 86646900HCID 86646900, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2,6-difluoro-N-(1-{[4-hydroxy-2-(trifluoromethyl)phenyl]methyl}-1H-pyrazol-3-yl)benzamide (for a preparation see Example 36)(100 mg, 0.252 mmol) in DMSO (1 ml) was added cesium carbonate (165 mg, 0.506 mmol) and then 4-(bromomethyl)pyridine hydrobromide (90 mg, 0.356 mmol, Aldrich) under nitrogen at ambient temperature. The resulting dark green suspension was then stirred for 7 h. A further amount of cesium carbonate (161 mg, 0.494 mmol) and then 4-(bromomethyl)pyridine hydrobromide (90 mg, 0.356 mmol, Aldrich) was added to the reaction mixture and stirred overnight. The mixture was filtered using a hydrophobic frit and the filtrate diluted with methanol (1 ml). The filtrate was purified by MDAP on Sunfire C18 column using Acetonitrile-Water with a TFA modifier (Method C). The solvent was evaporated in vacuo to give the title compound as a brown gum (44 mg);

Workup

  1. customat ambient temperature
  2. stirringstirred overnight
  3. filtrationThe mixture was filtered
  4. additionthe filtrate diluted with methanol (1 ml)
  5. customThe filtrate was purified by MDAP on Sunfire C18 column
  6. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-3361158df97a46ca8a22fac43aaa261f
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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