Methanol → HCID 22285054, compound

HRID 1061883Notes

Reaction equation

HRID 1061883 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([Br:17])[CH:13]=2)[C:8]=1[CH:18]=[O:19])(=O)=O.C(N(CC)CC)C.[CH3:29][OH:30].CN([CH:34]=[O:35])C>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]>[Br:17][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[C:8]1[CH:18]([O:35][CH3:34])[O:19][C:29](=[O:30])[C:7]=1[CH:16]=[CH:15]2

Participants

8

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 233981606-Bromo-1-formyl-2-naphthyl trifluoromethanesulfonate

Product 1

HCID 22285054HCID 22285054, compound

Reagents, catalysts & solvents 3

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

Procedure

A mixture of 6-bromo-1-formyl-2-naphthyl trifluoromethanesulfonate (5.62 g), triethylamine (5.12 mL), methanol (10 mL), palladium acetate (0.20 g), 1,1′-bis(diphenylphosphino)ferrocene (0.49 g) and DMF (30 mL) was stirred under a carbon monoxide atmosphere at room temperature for 3 hrs. The reaction mixture was diluted with ethyl acetate and washed successively with 10% citric acid, water and saturated aqueous sodium hydrogen carbonate, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography (carrier: silica gel, developing solvent: hexane-ethyl acetate, 20:1-3:1) to give the title compound (1.66 g) as colorless crystals.

Workup

  1. washwashed successively with 10% citric acid, water and saturated aqueous sodium hydrogen carbonate
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography (carrier: silica gel, developing solvent: hexane-ethyl acetate, 20:1-3:1)

Sources & evidence

ORD record
ord-6e0fc68f2b634d90bb8d87ab11531105
Source dataset
uspto-grants-2005_11
Patent number
US06960586B2

Reaction notes

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