Triethylsilane → HCID 57855975, compound

HRID 2039639Notes

Reaction equation

HRID 2039639 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[CH:10][C:11]([C:15]([F:18])([F:17])[F:16])=[N:12]2)=[C:7](OS(C(F)(F)F)(=O)=O)[C:6]=1[N+:27]([O-:29])=[O:28])=[O:4].C([SiH](CC)CC)C>CN(C)C=O.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[CH:10][C:11]([C:15]([F:17])([F:18])[F:16])=[N:12]2)=[CH:7][C:6]=1[N+:27]([O-:29])=[O:28])=[O:4]

Participants

7

Reactant 2

HCID 12052TriethylsilaneHCID 57855966HCID 57855966, compound

Product 1

HCID 57855975HCID 57855975, compoundYield 62.2%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 6-Nitro-5-trifluoromethanesulfonyloxy-2-trifluoromethyl-quinoline-7-carboxylic acid methyl ester (12.0 g, 24.094 mmol, step d, example H-18) is dissolved in dimethylformamide (50 ml) under argon and then treated with palladium(II)acetate (0.16 g, 0.723 mmol) and 1,1′bis(diphenylphosphino)ferrocene (0.4 g, 0.723 mmol). To this mixture at room temperature is added triethyl silane (7.0 g, 7.234 mmol) and the reaction then stirred overnight at room temperature. The reaction mixture is diluted with ethyl acetate and washed with brine. The ethyl acetate phase is dried over sodium sulphate, filtered and concentrated in vacuo. Purification of the residue by flash column chromatography (hexane:ethyl acetate, 6:1 as eluent) gives the title compound (4.5 g, 62%) as white crystals.

Workup

  1. customthe reaction
  2. washwashed with brine
  3. dry with materialThe ethyl acetate phase is dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue by flash column chromatography (hexane:ethyl acetate, 6:1 as eluent)

Sources & evidence

ORD record
ord-b56ecb75623e4bca8d4e7bbb90ed5ff0
Source dataset
uspto-grants-2013_11
Patent number
US08580785B2

Reaction notes

Loading…