Cesium carbonate → HCID 59547932, compound

HRID 1946381Notes

Reaction equation

HRID 1946381 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(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:36][CH2:37][O:38][CH3:39]>CS(C)=O>[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][CH2:36][CH2:37][O:38][CH3:39])=[CH:15][C:14]=2[C:20]([F:23])([F:21])[F:22])[N:8]=1)=[O:5]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 809722-Bromoethyl methyl etherHCID 59547990HCID 59547990, compound

Product 1

HCID 59547932HCID 59547932, 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)101 mg, 0.254 mmol) in DMSO (1 ml) was added cesium carbonate (166 mg, 0.508 mmol) and then 1-bromo-2-(methyloxy)ethane (0.035 ml, 0.372 mmol, Aldrich) under nitrogen at ambient temperature. The solution was stirred for 6 h. 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 Formic acid modifier (Method B). The solvent was evaporated in vacuo to give the title compound as a pale yellow gum (35 mg); LCMS: (System 4) MH+=456, tRET=2.84 min.

Workup

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

Sources & evidence

ORD record
ord-14f76f61d1cb4b4b880a1a1327d0882c
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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