Cesium carbonate → HCID 86662611, compound

HRID 1946378Notes

Reaction equation

HRID 1946378 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:39]=[N:40][CH:41]=[CH:42][CH:43]=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][O:30][CH2:37][C:38]3[CH:39]=[N:40][CH:41]=[CH:42][CH:43]=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 carbonateHCID 127070373-(Bromomethyl)pyridine hydrobromideHCID 59547990HCID 59547990, compound

Product 1

HCID 86662611HCID 86662611, 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 (166 mg, 0.509 mmol) and then 3-(bromomethyl)pyridine hydrobromide (89 mg, 0.352 mmol, Aldrich) at ambient temperature under nitrogen. The resulting yellow suspension was stirred for 3 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 TFA modifier (Method C). The solvent was evaporated in vacuo to give the title compound (65 mg) as a yellow solid; LCMS: (System 4) MH+=489, tRET=2.25 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-f8cdde9b227049108c122eb32a7ccfb5
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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