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

HRID 1946353Notes

Reaction equation

HRID 1946353 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[O:31][CH2:32][CH2:33][CH2:34][CH3:35].FC1C=CC=C(F)C=1C(NC1C=CN(CC2C=C(O)C=CC=2C)N=1)=O>CN(C)C=O>[CH2:32]([O:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][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)[CH2:33][CH2:34][CH3:35]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 201948961-(Bromomethyl)-2-butoxybenzeneHCID 595478422,6-Difluoro-N-{1-[(5-hydroxy-2-methylphenyl)methyl]-1H-pyrazol-3-yl}benzamideHCID 178522346HCID 178522346, compound

Product 1

HCID 59548017N-(1-{(2-(butyloxy)phenyl]methyl}-1H-pyrazol-3-yl)-2,6-difluorobenzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,6-Difluoro-N-1H-pyrazol-3-ylbenzamide (for a preparation see Intermediate 9)(89 mg, 0.40 mmol), potassium carbonate (83 mg, 0.60 mmol) and 1-(bromomethyl)-2-(butyloxy)benzene (for a preparation see Intermediate 2)(114 mg, 0.47 mmol) were weighed into a vial with a stirrer. N,N-dimethylformamide (1 ml) was added, the vial was capped and the mixture was stirred at room temperature for 28 h. The reaction mixture was filtered (hydrophobic frit), 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 (9.4 mg); LCMS: (System 4) MH+=386, tRET=3.17 min.

Workup

  1. customthe vial was capped
  2. filtrationThe reaction mixture was filtered (hydrophobic frit)
  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-c1c6f4c3e6bd445b9caa3dcb36379b88
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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