Methanol → HCID 89586284, compound

HRID 1747838Notes

Reaction equation

HRID 1747838 reaction equation
[CH3:1][O:2][C:3]1[C:4]([OH:20])=[C:5]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:12]=[CH:11][CH:10]=2)[N:6]=[N:7][CH:8]=1.[H-].[Na+].[F:23][C:24]([F:35])([F:34])[CH2:25]OS(C(F)(F)F)(=O)=O.CO>CN(C=O)C>[CH3:1][O:2][C:3]1[C:4](=[O:20])[C:5]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:12]=[CH:11][CH:10]=2)=[N:6][N:7]([CH2:25][C:24]([F:35])([F:34])[F:23])[CH:8]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 24758Sodium hydrideHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 178493808HCID 178493808, compound

Product 1

HCID 89586284HCID 89586284, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under an argon atmosphere, to a solution of 5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4-ol (2.0 g) in dehydrated DMF (40 ml) was added 60% NaH in oil (596 mg) while stirring under ice-cooling, and the mixture was stirred at the same temperature for 0.5 hr. Then, trifluoromethanesulfonic acid 2,2,2-trifluoroethyl ester (2.6 g) was added, and the mixture was stirred at room temperature for 18 hr. To the reaction mixture was added methanol, and the mixture was concentrated to dryness under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.71 g).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at the same temperature for 0.5 hr
  3. stirringthe mixture was stirred at room temperature for 18 hr
  4. concentrationthe mixture was concentrated to dryness under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e473418063bf4dcd9f6d358c68d24b71
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Reaction notes

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