2-(Tributylstannyl)pyridine → HCID 6417974, compound

HRID 574178Notes

Reaction equation

HRID 574178 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>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=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

4

Reactant 2

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

Product 1

HCID 6417974HCID 6417974, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Stille coupling starting from the 6,6′-dichloro-3,3′-bipyridazine 17 was subsequently carried out in the presence of two mol of tributylstannylpyridine 18 and 10% of Pd(PPh3)4 catalyst, so as to give a new 6,6′-bis(pyridin-2-yl)-3,3′-bipyridazine 19 with a yield of 62% (Scheme 8). In parallel, the formation of the homocoupling product 21 (23%) was observed. The use of an excess of organostannane makes the purification of the dimer more difficult.

Sources & evidence

ORD record
ord-6d0e2075946847e39866a4c526e1c423
Source dataset
uspto-grants-2015_05
Patent number
US09034873B2

Reaction notes

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