HCID 6417980, compound → 2,2'-Bipyridine

HRID 574179Notes

Reaction equation

HRID 574179 reaction equation
ClC1C=CN=NC=1C1C=CC=CN=1.C([Sn](CCCC)(CCCC)[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]2[N:30]=[C:29]([Sn](CCCC)(CCCC)CCCC)[CH:28]=[CH:27][CH:26]=2)[N:20]=1)CCC.N1C=CC=CC=1C1N=NC(C2N=C(C3C=CC=C(C4N=NC(C5C=CC=CN=5)=CC=4)N=3)C=CC=2)=CC=1>>[CH:27]1[CH:28]=[CH:29][N:30]=[C:25]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:19][N:20]=2)[CH:26]=1

Participants

4

Reactant 3

HCID 6417980HCID 6417980, compoundHCID 59592001HCID 59592001, compoundHCID 67041290HCID 67041290, compound2×

Product 1

HCID 14742,2'-BipyridineYield 68%

Procedure

Stille coupling of two mol of 3-chloro-6-(pyridin-2-yl)pyridazine 8a with the precursor 2,2′-bis(tributylstannyl)-6,6′-bipyridine 60 gives the disubstituted product 61 with a yield of 68% (Scheme 28). In practice, a slight excess of chloropyridazine 8a is added in order for all the monosubstituted product formed to be consumed.

Workup

  1. customformed
  2. customto be consumed

Sources & evidence

ORD record
ord-5e13de0eab114a6fa99fb440785d6994
Source dataset
uspto-grants-2015_05
Patent number
US09034873B2

Reaction notes

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