Potassium Carbonate → 2,6-Difluoro-N-(1-{[2-(phenylmethyl)phenyl]methyl}-1H-pyrazol-3-yl)benzamide

HRID 1946354Notes

Reaction equation

HRID 1946354 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:3]=1[C:4]([NH:6][C:7]1[CH:11]=[CH:10][NH:9][N:8]=1)=[O:5].C(=O)([O-])[O-].[K+].[K+].Br[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CN(C=O)C>[F:1][C:2]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:3]=1[C:4]([NH:6][C:7]1[CH:11]=[CH:10][N:9]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:8]=1)=[O:5]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 124220982-Benzyl benzylbromideHCID 178522346HCID 178522346, compound

Product 1

HCID 595479062,6-Difluoro-N-(1-{[2-(phenylmethyl)phenyl]methyl}-1H-pyrazol-3-yl)benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,6-Difluoro-N-1H-pyrazol-3-ylbenzamide (for a preparation see Intermediate 9)(45 mg, 0.202 mmol), potassium carbonate (42 mg, 0.304 mmol) and 1-(bromomethyl)-2-(phenylmethyl)benzene (for a preparation see Intermediate 3)(64 mg, 0.245 mmol) were weighed into a vial with a stirrer. DMF (1 ml) was added, the vial was capped and the mixture was stirred at room temperature for 17 h. The reaction mixture was filtered, washing with MeOH to give a total volume of 2 ml. This solution was purified by MDAP (Sunfire column, formic acid buffer) (Method B). The solvent was removed to give the title compound as a colourless solid (10 mg); LCMS: (System 4) MH+=404, tRET=3.23 min.

Workup

  1. customthe vial was capped
  2. filtrationThe reaction mixture was filtered
  3. washwashing with MeOH
  4. customto give a total volume of 2 ml
  5. customThis solution was purified by MDAP (Sunfire column, formic acid buffer) (Method B)
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-16b6b332a7db4ae081f7f80f6b6a7fce
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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