2-(Tributylstannyl)pyridine → HCID 44224663, compound

HRID 1914550Notes

Reaction equation

HRID 1914550 reaction equation
[N:1]1([C:7]([C:9]2[CH:13]=[C:12](Br)[S:11][CH:10]=2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([Sn](CCCC)(CCCC)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1)CCC>C1(C)C=CC=CC=1.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:1]1([C:7]([C:9]2[CH:13]=[C:12]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)[S:11][CH:10]=2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 40012281HCID 40012281, compound

Product 1

HCID 44224663HCID 44224663, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of piperidin-1-yl-(5-bromo-thiophen-3-yl)-methanone (76 mg, 1 eq.), tributyl(2-pyridyl)tin (0.102 mL, 1 eq.) and PdCl2(PPh3)2 (0.011 g, 0.1 eq) were heated at 100° C. in toluene (1 mL) for 6 hours. The solvent was evaporated and the residue purified by column chromatography (EtOAc/iso-hexane) to give the desired product (9.2 mg, 12%). LCMS m/z 273 [M+H]+ R.T.=2.73 min (Analytical Method 3).

Workup

  1. customThe solvent was evaporated
  2. customthe residue purified by column chromatography (EtOAc/iso-hexane)

Sources & evidence

ORD record
ord-666ce1a5af904ca997b27b9a368b64f1
Source dataset
uspto-grants-2013_12
Patent number
US08614209B2

Reaction notes

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