2-(Tributylstannyl)pyridine → HCID 6417974, compound

HRID 574185Notes

Reaction equation

HRID 574185 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([C:8]2[N:9]=[N:10][C:11](Cl)=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1)CCC>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[N:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:2]1[N:7]=[N:6][C:5]([C:8]2[N:9]=[N:10][C:11]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:20][N:21]=3)=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 498002428732-46-9

Product 1

HCID 6417974HCID 6417974, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

The 6,6′-bis(pyridin-2-yl)-3,3′-bipyridazine 19 was prepared according to the general Stille coupling procedure, starting from a reaction mixture of 500 mg (4.42 mmol) of dichlorobipyridazine 17, 2.03 g (5.52 mmol) of 6-tributylstannylpyridine 18 and 387 mg (0.55 mmol) of dichlorobis(triphenylphosphine)-palladium(II), in 40 ml of DMF. The reaction mixture is heated at 95° C. for 24 h. The residue obtained is purified by silica gel chromatography (eluent: ethyl acetate/petroleum ether=1/9). The disubstituted product 19 is isolated with a yield of 62%.

Workup

  1. customThe 6,6′-bis(pyridin-2-yl)-3,3′-bipyridazine 19 was prepared
  2. customThe residue obtained
  3. customis purified by silica gel chromatography (eluent: ethyl acetate/petroleum ether=1/9)

Sources & evidence

ORD record
ord-f6e546a5675b40d58f827002f35fbe01
Source dataset
uspto-grants-2015_05
Patent number
US09034873B2

Reaction notes

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