Triphenylphosphine → 6-Trimethylsilylethynyl-8-(3-nitrophenyl)-1,7-naphthyridine

HRID 369031Notes

Reaction equation

HRID 369031 reaction equation
FC(F)(F)S(O[C:7]1[CH:8]=[C:9]2[C:14](=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=3)[N:16]=1)[N:13]=[CH:12][CH:11]=[CH:10]2)(=O)=O.[C:28]([Si:30]([CH3:33])([CH3:32])[CH3:31])#[CH:29].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C)C=O.C(N(CC)CC)C.C(OCC)(=O)C.[Cu](I)I>[CH3:31][Si:30]([C:28]#[C:29][C:7]1[CH:8]=[C:9]2[C:14](=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=3)[N:16]=1)[N:13]=[CH:12][CH:11]=[CH:10]2)([CH3:33])[CH3:32]

Participants

8

Reactant 3

HCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 108109346-Trifluoromethylsulfonyloxy-8-(3-nitrophenyl)-1,7-naphthyridine

Product 1

HCID 232846376-Trimethylsilylethynyl-8-(3-nitrophenyl)-1,7-naphthyridine

Reagents, catalysts & solvents 4

HCID 83717Copper iodideCatalystHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-trifluoromethylsulfonyloxy-8-(3-nitrophenyl)-1,7-naphthyridine (200 mg, 0.50 mmol; prepared according to example 13) in dimethylformamide (1 ml) and triethylamine (0.5 ml) is added ethynyltrimethylsilane (0.078 ml, 0.56 mmol), bis(dibensylideneacetone)palladium (5.8 mg, 0.020 mmol), triphenylphosphine (5.3 mg, 0.020 mmol) and copper iodide (3.8 mg, 0.020 mmol). The mixture is kept at 60° C. for 2 h. The solution is diluted with ethyl acetate and washed with water. The product is purified by flash column chromatography on silica gel (20:0.2 toluene/acetone) affording 6-trimethylsilylethynyl-8-(3-nitrophenyl)-1,7-naphthyridine. (Mass M+H 348; mp 160-163° C.)

Workup

  1. washwashed with water
  2. customThe product is purified by flash column chromatography on silica gel (20:0.2 toluene/acetone)

Sources & evidence

ORD record
ord-461c80cb2d6143afb7cffdcfb39eef8e
Source dataset
uspto-grants-2000_10
Patent number
US06136821

Reaction notes

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