Cesium carbonate → 2,6-Difluoro-N-{1-[(2-methyl-5-{[3-(methyloxy)propyl]oxy}phenyl)methyl]-1H-pyrazol-3-yl}benzamide
Reaction equation
[F:1][C:2]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:3]=1[C:4]([NH:6][C:7]1[CH:11]=[CH:10][N:9]([CH2:12][C:13]2[CH:18]=[C:17]([OH:19])[CH:16]=[CH:15][C:14]=2[CH3:20])[N:8]=1)=[O:5].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:33][CH2:34][CH2:35][O:36][CH3:37]>CS(C)=O>[F:1][C:2]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:3]=1[C:4]([NH:6][C:7]1[CH:11]=[CH:10][N:9]([CH2:12][C:13]2[CH:18]=[C:17]([O:19][CH2:33][CH2:34][CH2:35][O:36][CH3:37])[CH:16]=[CH:15][C:14]=2[CH3:20])[N:8]=1)=[O:5]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2,6-difluoro-N-{1-[(5-hydroxy-2-methylphenyl)methyl]-1H-pyrazol-3-yl}benzamide (for a preparation see Intermediate 49)(82 mg, 0.239 mmol) in DMSO (1 ml) was added cesium carbonate (155 mg, 0.476 mmol) and then a solution of 1-bromo-3-(methyloxy)propane (45 mg, 0.294 mmol, Matrix Scientific) in DMSO (0.1 ml). The resulting red solution was stirred at ambient temperature under nitrogen overnight. The solution was filtered using a hydrophobic frit and diluted with methanol (0.9 ml). The mixture was purified by MDAP on a Sunfire C18 column (Method B) using Acetonitrile-Water with a Formic acid modifier. The solvent was evaporated in vacuo to give the title compound as a luminous yellow gum (19.4 mg); LCMS (System 4) MH+=416, tRET=2.79 min.
Workup
- filtrationThe solution was filtered
- additiondiluted with methanol (0.9 ml)
- customThe mixture was purified by MDAP on a Sunfire C18 column (Method B)
- customThe solvent was evaporated in vacuo
Sources & evidence
- ORD record
- ord-78e1b8e283fa4200951a3a7f1ae1f409
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08399436B2
Reaction notes
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