3-Iodopyridine → 3-Isopropoxy-4-(3-pyridyl)-cyclobut-3-ene-1,2-dione

HRID 990771

Reaction equation

HRID 990771 reaction equation
[CH:1]([O:4][C:5]1[C:6](=[O:23])[C:7](=[O:22])[C:8]=1[Sn](CCCC)(CCCC)CCCC)([CH3:3])[CH3:2].I[C:25]1[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=1>>[CH:1]([O:4][C:5]1[C:6](=[O:23])[C:7](=[O:22])[C:8]=1[C:25]1[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=1)([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 707143-IodopyridineHCID 27366833-Isopropoxy-4-(tri-n-butylstannyl)-3-cyclobutene-1,2-dione

Product 1

HCID 120516723-Isopropoxy-4-(3-pyridyl)-cyclobut-3-ene-1,2-dione

Procedure

In a manner similar to Example 9, Step 1, 3-isopropoxy-4-(tri-n-butylstannyl)-3-cyclobutene-1,2-dione (1.90 g, 4.43 mmol), 3-iodopyridine (1.00 g, 4.87 mmol), benzylchlorobis(triphenylphosphine)palladium (II) (0.201 g, 0.267 mmol), and cuprous iodide (0.076 g, 0.399 mmol) were reacted together to give the title compound which was of sufficient purity to use in the next step: 1H NMR (DMSO-d6) δ9.07(m,1H), 8.75(m,1H), 8.20(br d,1H), 7.65(m,1H), 5.50(sept,1H), 1.50(d,6H).

Sources & evidence

ORD record
ord-97de646ddda24e35beebc5106fd3ca08
Source dataset
uspto-grants-2002_10
Patent number
US06462059B1

Linked notes

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