Phenol → HCID 12109652, compound

HRID 1838862Notes

Reaction equation

HRID 1838862 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[C:18](=[O:32])[NH:19][NH:20][C:21]=2[C:22]2[CH:27]=[CH:26][N:25]=[C:24](S(C)(=O)=O)[N:23]=2)=[CH:13][CH:12]=1>C1COCC1.C([O-])(O)=O.[Na+]>[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[C:18](=[O:32])[NH:19][NH:20][C:21]=2[C:22]2[CH:27]=[CH:26][N:25]=[C:24]([O:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[N:23]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 996PhenolHCID 24758Sodium hydrideHCID 12109651HCID 12109651, compound

Product 1

HCID 12109652HCID 12109652, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of phenol (0.66 g, 7.08 mmol) in THF (5 mL) is added NaH (0.24 g, 5.91 mmol) followed by a solution of the crude 4-(4-fluorophenyl)-5-(2-methanesulfonylpyrimidin-4-yl)-1,2-dihydro-pyrazol-3-one, 5, prepared herein above (0.22 g, 0.67 mmol) in THF (2 mL). The reaction mixture is stirred for 1.5 hours at room temperature, diluted with aqueous NaHCO3 and extracted with twice with ethyl acetate. The organic layers are combined, dried over MgSO4, and concentrated in vacuo to afford the crude product which is purified over silica (100% EtOAc, followed by 10% MeOH/EtOAc) to provide the desired product as a yellow solid.

Workup

  1. extractionextracted with twice with ethyl acetate
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customto afford the crude product which
  5. customis purified over silica (100% EtOAc, followed by 10% MeOH/EtOAc)

Sources & evidence

ORD record
ord-cbb9b2aa78334be198dd63378b673b4b
Source dataset
uspto-grants-2004_01
Patent number
US06677337B2

Reaction notes

Loading…