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

HRID 1946300Notes

Reaction equation

HRID 1946300 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[C:30]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:29][CH:28]=[CH:27][C:26]=1[Cl:39]>CN(C=O)C>[Cl:39][C:26]1[CH:27]=[CH:28][CH:29]=[C:30]([O:31][CH2:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:25]=1[CH2:24][N:9]1[CH:10]=[CH:11][C:7]([NH:6][C:4](=[O:5])[C:3]2[C:12]([F:16])=[CH:13][CH:14]=[CH:15][C:2]=2[F:1])=[N:8]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 595479962-(Bromomethyl)-1-chloro-3-[(phenylmethyl)oxy]benzeneHCID 178522346HCID 178522346, compound

Product 1

HCID 59547897N-[1-({2-Chloro-6-[(phenylmethyl)oxy]phenyl}methyl)-1H-pyrazol-3-yl]-2,6-difluorobenzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2,6-difluoro-N-(1H-pyrazol-3-yl)benzamide (for a preparation see Intermediate 9) (0.360 g, 1.61 mmol) and potassium carbonate (0.308 g, 2.23 mmol) was added a solution 2-(bromomethyl)-1-chloro-3-[(phenylmethyl)oxy]benzene (for a preparation see Intermediate 8)(0.50 g, 1.61 mmol) in DMF (5 ml). The suspension was stirred overnight at ambient temperature. The suspension was partitioned between ethyl acetate (30 ml) and water (30 ml). The phases were separated and the organic phase washed with ethyl acetate (30 ml). The combined organic extracts were washed with brine (30 ml) and the solvent removed in vacuo. The residue was loaded in dichloromethane and purified on silica 50 g using 0-50% ethyl acetate-cyclohexane. The appropriate fractions were combined and evaporated in vacuo to give the title compound as a white solid (0.212 g); LCMS: (System 1) MH+=455, tRET=3.59 min.

Workup

  1. customThe suspension was partitioned between ethyl acetate (30 ml) and water (30 ml)
  2. customThe phases were separated
  3. washthe organic phase washed with ethyl acetate (30 ml)
  4. washThe combined organic extracts were washed with brine (30 ml)
  5. customthe solvent removed in vacuo
  6. custompurified on silica 50 g
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-d6afad93988045a5910276dc4c3ca229
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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