HCID 59140934, compound → HCID 24944673, compound

HRID 574188Notes

Reaction equation

HRID 574188 reaction equation
[Br:1][C:2]1(C2C=CC=CN=2)[CH:7]=[CH:6][CH:5]=[C:4](Br)[NH:3]1.[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]1[N:26]=[N:25][C:24]([Sn](CCCC)(CCCC)CCCC)=[CH:23][CH:22]=1>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1>[Br:1][C:2]1[N:3]=[C:4]([C:24]2[N:25]=[N:26][C:21]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][N:15]=3)=[CH:22][CH:23]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 59140934HCID 59140934, compoundHCID 67041324HCID 67041324, compound

Product 1

HCID 24944673HCID 24944673, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Procedure

The 3-(6-bromopyridin-2-yl)-6-(pyridin-2-yl)pyridazine was prepared according to the general Stille coupling method, starting from a mixture of 1.6 g (6.74 mmol) of 2,6-dibromobipyridine 42, 3 g (6.74 mmol) of 6-(pyridin-2-yl)-3-(tributylstannyl)pyridazine 39, 546 mg (0.47 mmol) of tetrakis(triphenylphosphine)-palladium(0) and 50 ml of freshly distilled toluene. The mixture is refluxed for 24 h. The residue obtained is chromatographed on a silica gel (eluent: ethyl acetate/petroleum ether=1/9). The brominated product 43 is isolated with a yield of 72%.

Workup

  1. customThe 3-(6-bromopyridin-2-yl)-6-(pyridin-2-yl)pyridazine was prepared
  2. temperatureThe mixture is refluxed for 24 h
  3. customThe residue obtained
  4. customis chromatographed on a silica gel (eluent: ethyl acetate/petroleum ether=1/9)

Sources & evidence

ORD record
ord-f06685422dce4b4c8bce890fa98569d4
Source dataset
uspto-grants-2015_05
Patent number
US09034873B2

Reaction notes

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